-- Table structure for table `django_content_type`
--

CREATE TABLE `django_content_type` (
  `id` int NOT NULL AUTO_INCREMENT,
  `app_label` varchar(100) NOT NULL,
  `model` varchar(100) NOT NULL,
  PRIMARY KEY (`id`),
  UNIQUE KEY `django_content_type_app_label_model_76bd3d3b_uniq` (`app_label`,`model`)
) ENGINE=InnoDB AUTO_INCREMENT=39 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_0900_ai_ci;

--
-- Dumping data for table `django_content_type`
--

INSERT INTO `django_content_type` VALUES (1,'admin','logentry'),(3,'auth','group'),(2,'auth','permission'),(4,'auth','user'),(8,'blog','category'),(10,'blog','comment'),(34,'blog','g_data'),(9,'blog','post'),(33,'blog','s_data'),(22,'carriers','carrier_create'),(21,'carriers','carriers'),(18,'categories','category'),(5,'contenttypes','contenttype'),(38,'django_check_seo','djangocheckseopermissions'),(15,'django_summernote','attachment'),(20,'drugs','drugs'),(11,'home','contact'),(36,'home','faq'),(26,'home','newsletter'),(37,'home','team'),(12,'news','category'),(14,'news','comment'),(13,'news','news'),(35,'rsslink','external_link'),(25,'rsslink','rsslink'),(6,'sessions','session'),(7,'sites','site'),(28,'social_django','association'),(29,'social_django','code'),(30,'social_django','nonce'),(32,'social_django','partial'),(31,'social_django','usersocialauth'),(16,'taggit','tag'),(17,'taggit','taggeditem'),(19,'university','university'),(23,'webinar','webinar'),(24,'webinar','webinar_category'),(27,'webinar','webinar_register');

--
-- Table structure for table `django_migrations`
--

CREATE TABLE `django_migrations` (
  `id` int NOT NULL AUTO_INCREMENT,
  `app` varchar(255) NOT NULL,
  `name` varchar(255) NOT NULL,
  `applied` datetime(6) NOT NULL,
  PRIMARY KEY (`id`)
) ENGINE=InnoDB AUTO_INCREMENT=119 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_0900_ai_ci;

--
-- Dumping data for table `django_migrations`
--

INSERT INTO `django_migrations` VALUES (1,'contenttypes','0001_initial','2022-02-23 03:04:14.123387'),(2,'auth','0001_initial','2022-02-23 03:04:16.427547'),(3,'admin','0001_initial','2022-02-23 03:04:18.334937'),(4,'admin','0002_logentry_remove_auto_add','2022-02-23 03:04:18.753653'),(5,'admin','0003_logentry_add_action_flag_choices','2022-02-23 03:04:18.877108'),(6,'contenttypes','0002_remove_content_type_name','2022-02-23 03:04:19.381595'),(7,'auth','0002_alter_permission_name_max_length','2022-02-23 03:04:19.633298'),(8,'auth','0003_alter_user_email_max_length','2022-02-23 03:04:19.845778'),(9,'auth','0004_alter_user_username_opts','2022-02-23 03:04:19.976874'),(10,'auth','0005_alter_user_last_login_null','2022-02-23 03:04:20.213615'),(11,'auth','0006_require_contenttypes_0002','2022-02-23 03:04:20.345997'),(12,'auth','0007_alter_validators_add_error_messages','2022-02-23 03:04:20.486509'),(13,'auth','0008_alter_user_username_max_length','2022-02-23 03:04:20.740900'),(14,'auth','0009_alter_user_last_name_max_length','2022-02-23 03:04:20.992308'),(15,'auth','0010_alter_group_name_max_length','2022-02-23 03:04:21.187248'),(16,'auth','0011_update_proxy_permissions','2022-02-23 03:04:21.477398'),(17,'auth','0012_alter_user_first_name_max_length','2022-02-23 03:04:21.721025'),(18,'taggit','0001_initial','2022-02-23 03:04:22.457743'),(19,'taggit','0002_auto_20150616_2121','2022-02-23 03:04:23.166313'),(20,'taggit','0003_taggeditem_add_unique_index','2022-02-23 03:04:23.377325'),(21,'blog','0001_initial','2022-02-23 03:04:25.458020'),(22,'django_summernote','0001_initial','2022-02-23 03:04:26.836606'),(23,'django_summernote','0002_update-help_text','2022-02-23 03:04:26.966517'),(24,'django_summernote','0003_alter_attachment_id','2022-02-23 03:04:27.191252'),(25,'django_summernote','0004_auto_20220209_1726','2022-02-23 03:04:27.411202'),(26,'home','0001_initial','2022-02-23 03:04:27.935784'),(27,'news','0001_initial','2022-02-23 03:04:29.705400'),(28,'sessions','0001_initial','2022-02-23 03:04:30.760276'),(29,'sites','0001_initial','2022-02-23 03:04:31.196583'),(30,'sites','0002_alter_domain_unique','2022-02-23 03:04:31.377636'),(31,'categories','0001_initial','2022-02-23 03:26:13.246218'),(32,'blog','0002_auto_20220223_0856','2022-02-23 03:26:14.803997'),(33,'news','0002_auto_20220223_0858','2022-02-23 03:29:03.154068'),(34,'blog','0003_auto_20220223_1155','2022-02-23 06:26:52.423371'),(35,'blog','0004_auto_20220223_1156','2022-02-23 06:26:52.559027'),(36,'news','0003_news_journal_reference','2022-02-23 06:26:52.978764'),(37,'blog','0005_alter_comment_id_alter_post_id','2022-02-23 11:20:21.854107'),(38,'categories','0002_alter_category_id','2022-02-23 11:20:22.638246'),(39,'home','0002_alter_contact_id','2022-02-23 11:20:22.699189'),(40,'news','0004_alter_comment_id_alter_news_id','2022-02-23 11:20:23.003991'),(41,'taggit','0004_alter_taggeditem_content_type_alter_taggeditem_tag','2022-02-23 11:20:23.039386'),(43,'university','0002_auto_20220226_1457','2022-02-26 09:28:04.882038'),(44,'categories','0002_category_created_on','2022-02-26 16:51:48.272168'),(45,'university','0003_auto_20220228_1117','2022-02-28 05:52:07.390143'),(46,'university','0004_university_fax_number','2022-02-28 05:52:07.836870'),(47,'university','0005_university_overview','2022-02-28 05:52:08.282090'),(48,'categories','0003_remove_category_created_on','2022-02-28 07:23:03.162549'),(49,'university','0001_initial','2022-02-28 07:28:16.786486'),(50,'university','0002_university_acrynon_and_more','2022-02-28 11:35:53.680165'),(51,'university','0003_alter_university_acrynon_and_more','2022-02-28 12:46:33.013714'),(52,'blog','0006_auto_20220301_1555','2022-03-01 10:28:05.477238'),(53,'categories','0003_auto_20220301_1555','2022-03-01 10:28:09.697620'),(54,'home','0003_auto_20220301_1555','2022-03-01 10:28:10.055103'),(55,'news','0005_auto_20220301_1555','2022-03-01 10:28:11.814531'),(56,'university','0004_auto_20220301_1555','2022-03-01 10:28:12.112435'),(57,'categories','0003_category_created_on','2022-03-05 05:37:40.209147'),(58,'drugs','0001_initial','2022-03-13 18:20:59.046350'),(59,'drugs','0002_auto_20220314_0007','2022-03-13 18:37:31.798954'),(60,'drugs','0003_auto_20220314_0042','2022-03-13 19:13:15.811643'),(61,'drugs','0004_auto_20220314_0148','2022-03-13 20:18:58.274708'),(62,'drugs','0005_auto_20220314_0148','2022-03-13 20:18:58.494686'),(63,'taggit','0005_auto_20220424_2025','2022-05-04 17:48:18.872109'),(65,'carriers','0002_carriers_carrier_field','2022-08-17 12:13:06.420326'),(66,'carriers','0003_alter_carriers_phone','2022-08-17 12:30:01.669523'),(67,'carriers','0004_alter_carriers_whats_app_number','2022-08-17 12:32:55.337609'),(68,'carriers','0005_alter_carriers_carrier_field','2022-08-18 05:19:41.895457'),(69,'home','0003_alter_contact_phone','2022-08-19 09:14:20.245764'),(70,'carriers','0006_auto_20220905_1952','2022-09-06 04:16:30.189849'),(71,'carriers','0007_auto_20220906_1226','2022-09-06 12:26:17.628362'),(72,'carriers','0008_carrier_create','2022-10-06 20:09:36.160775'),(73,'carriers','0009_auto_20221007_0726','2022-10-07 07:26:40.085010'),(74,'webinar','0001_initial','2022-10-07 21:12:43.576895'),(75,'carriers','0001_initial','2022-10-07 23:01:32.118442'),(76,'webinar','0002_auto_20221008_0715','2022-10-08 07:15:37.052046'),(77,'webinar','0003_auto_20221008_0717','2022-10-08 07:17:43.091627'),(78,'rsslink','0001_initial','2022-10-08 09:04:37.210343'),(79,'home','0004_newsletter','2022-10-10 19:50:52.306759'),(80,'webinar','0004_auto_20221026_1712','2022-10-26 17:12:34.172248'),(81,'default','0001_initial','2022-12-08 07:09:06.465045'),(82,'social_auth','0001_initial','2022-12-08 07:09:06.480057'),(83,'default','0002_add_related_name','2022-12-08 07:09:06.511618'),(84,'social_auth','0002_add_related_name','2022-12-08 07:09:06.520330'),(85,'default','0003_alter_email_max_length','2022-12-08 07:09:06.547394'),(86,'social_auth','0003_alter_email_max_length','2022-12-08 07:09:06.555716'),(87,'default','0004_auto_20160423_0400','2022-12-08 07:09:06.601736'),(88,'social_auth','0004_auto_20160423_0400','2022-12-08 07:09:06.611322'),(89,'social_auth','0005_auto_20160727_2333','2022-12-08 07:09:06.645133'),(90,'social_django','0006_partial','2022-12-08 07:09:06.716035'),(91,'social_django','0007_code_timestamp','2022-12-08 07:09:06.794534'),(92,'social_django','0008_partial_timestamp','2022-12-08 07:09:06.856321'),(93,'social_django','0009_auto_20191118_0520','2022-12-08 07:09:06.956206'),(94,'social_django','0010_uid_db_index','2022-12-08 07:09:07.004433'),(95,'social_django','0003_alter_email_max_length','2022-12-08 07:09:07.019293'),(96,'social_django','0004_auto_20160423_0400','2022-12-08 07:09:07.026985'),(97,'social_django','0001_initial','2022-12-08 07:09:07.032984'),(98,'social_django','0005_auto_20160727_2333','2022-12-08 07:09:07.040303'),(99,'social_django','0002_add_related_name','2022-12-08 07:09:07.047995'),(100,'blog','0006_s_data','2022-12-22 04:25:18.611093'),(101,'blog','0002_auto_20221222_0546','2022-12-22 05:52:38.660013'),(102,'blog','0003_auto_20221222_0602','2022-12-22 06:02:58.671141'),(103,'rsslink','0002_external_link','2022-12-23 10:52:50.844620'),(104,'home','0005_faq','2023-01-17 07:18:49.751619'),(105,'home','0006_team','2023-01-17 09:08:11.011152'),(106,'home','0007_alter_team_status','2023-02-03 10:15:00.186224'),(107,'home','0008_alter_team_status','2023-02-04 10:56:22.676196'),(108,'home','0009_alter_team_status','2023-02-04 11:08:36.801679'),(109,'home','0010_alter_team_status','2023-02-04 11:10:49.272769'),(110,'carriers','0002_carriers_status','2023-02-07 07:01:34.517597'),(111,'home','0011_alter_team_status','2023-02-19 09:53:56.415098'),(112,'django_check_seo','0001_initial','2024-04-06 05:05:28.689555'),(113,'social_django','0011_alter_id_fields','2024-04-06 05:05:29.771524'),(114,'social_django','0012_usersocialauth_extra_data_new','2024-04-06 05:05:30.163285'),(115,'social_django','0013_migrate_extra_data','2024-04-06 05:05:30.337435'),(116,'social_django','0014_remove_usersocialauth_extra_data','2024-04-06 05:05:30.499410'),(117,'social_django','0015_rename_extra_data_new_usersocialauth_extra_data','2024-04-06 05:05:30.666635'),(118,'taggit','0006_rename_taggeditem_content_type_object_id_taggit_tagg_content_8fc721_idx','2024-04-06 05:05:31.023831');

--
-- Table structure for table `django_session`
--

CREATE TABLE `django_session` (
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  `session_data` longtext NOT NULL,
  `expire_date` datetime(6) NOT NULL,
  PRIMARY KEY (`session_key`),
  KEY `django_session_expire_date_a5c62663` (`expire_date`)
) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_0900_ai_ci;

--
-- Dumping data for table `django_session`
--

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--
-- Table structure for table `django_site`
--

CREATE TABLE `django_site` (
  `id` int NOT NULL AUTO_INCREMENT,
  `domain` varchar(100) NOT NULL,
  `name` varchar(50) NOT NULL,
  PRIMARY KEY (`id`),
  UNIQUE KEY `django_site_domain_a2e37b91_uniq` (`domain`)
) ENGINE=InnoDB AUTO_INCREMENT=3 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_0900_ai_ci;

--
-- Dumping data for table `django_site`
--

INSERT INTO `django_site` VALUES (1,'educracypedia.com','educracypedia.com');

--
-- Table structure for table `django_summernote_attachment`
--

CREATE TABLE `django_summernote_attachment` (
  `id` int NOT NULL AUTO_INCREMENT,
  `name` varchar(255) DEFAULT NULL,
  `file` varchar(100) NOT NULL,
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--
-- Table structure for table `drugs_drugs`
--

CREATE TABLE `drugs_drugs` (
  `id` int NOT NULL AUTO_INCREMENT,
  `title` varchar(200) NOT NULL,
  `slug` varchar(200) NOT NULL,
  `summary` longtext NOT NULL,
  `brand_name` varchar(500) NOT NULL,
  `Generic_Name` varchar(200) NOT NULL,
  `Background` longtext NOT NULL,
  `Chemical_Formula` varchar(200) NOT NULL,
  `DrugBank_Accession_Number` varchar(200) NOT NULL,
  `Drugs_Groups` varchar(200) NOT NULL,
  `Drugs_Type` varchar(200) NOT NULL,
  `Weight` varchar(200) NOT NULL,
  `ATC_Codes` longtext NOT NULL,
  `Absorption` longtext NOT NULL,
  `Adverse_Effects` longtext NOT NULL,
  `Affected_organisms` longtext NOT NULL,
  `Alternative_Parents` longtext NOT NULL,
  `Associated_Conditions` longtext NOT NULL,
  `Associated_Therapies` longtext NOT NULL,
  `BindingDB` longtext NOT NULL,
  `CAS_number` varchar(300) NOT NULL,
  `ChEBI` longtext NOT NULL,
  `ChEMBL` longtext NOT NULL,
  `ChemSpider` longtext NOT NULL,
  `Chemical_Taxonomy` longtext NOT NULL,
  `Class` longtext NOT NULL,
  `Clearance` longtext NOT NULL,
  `Drugs_Description` longtext NOT NULL,
  `Direct_Parent` longtext NOT NULL,
  `Drug_Interactions` longtext NOT NULL,
  `Drugs` longtext NOT NULL,
  `Drugs_Catergories` longtext NOT NULL,
  `Experimental_Properties` longtext NOT NULL,
  `External_Descriptors` longtext NOT NULL,
  `External_Links` longtext NOT NULL,
  `Food_Interactions` longtext NOT NULL,
  `General_References` longtext NOT NULL,
  `Half_life` longtext NOT NULL,
  `Human_Metabolome_Database` longtext NOT NULL,
  `IUPAC_Name` varchar(300) NOT NULL,
  `InChI` varchar(300) NOT NULL,
  `InChI_Key` varchar(300) NOT NULL,
  `Indication` longtext NOT NULL,
  `KEGG_Compound` longtext NOT NULL,
  `KEGG_Drug` longtext NOT NULL,
  `Kingdom` longtext NOT NULL,
  `Metabolism` longtext NOT NULL,
  `Molecular_Framework` longtext NOT NULL,
  `PDBe_Ligand` longtext NOT NULL,
  `Pathways` longtext NOT NULL,
  `PharmGKB` longtext NOT NULL,
  `Protein_binding` longtext NOT NULL,
  `PubChem_Compound` longtext NOT NULL,
  `PubChem_Substance` longtext NOT NULL,
  `Route_of_elimination` longtext NOT NULL,
  `RxList` longtext NOT NULL,
  `RxNav` longtext NOT NULL,
  `SMILES` varchar(300) NOT NULL,
  `State` longtext NOT NULL,
  `Sub_class` longtext NOT NULL,
  `Substituents` longtext NOT NULL,
  `Super_Class` longtext NOT NULL,
  `Synthesis_Reference` longtext NOT NULL,
  `Therapeutic_Targets_Database` longtext NOT NULL,
  `Toxicity` longtext NOT NULL,
  `UNII` varchar(300) NOT NULL,
  `Volume_of_distribution` longtext NOT NULL,
  `Wikipedia` longtext NOT NULL,
  `ZINC` longtext NOT NULL,
  PRIMARY KEY (`id`),
  UNIQUE KEY `title` (`title`),
  UNIQUE KEY `slug` (`slug`)
) ENGINE=InnoDB AUTO_INCREMENT=101 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_0900_ai_ci;

--
-- Dumping data for table `drugs_drugs`
--

INSERT INTO `drugs_drugs` VALUES (9,'Acetaminophen','acetaminophen','Acetaminophen is an analgesic drug used alone or in combination with opioids for pain management, and as an antipyretic agent.','Acephen, Acetadryl, Allzital, Apadaz, Arthriten Inflammatory Pain, Bupap, Butapap, Cetafen, Children\'s Silapap, Contac Cold and Flu Non Drowsy Maximum Strength, Coricidin Hbp Cold & Flu, Darvocet-N, Dayquil Sinex, Dolofin, Dologen, Dologesic Reformulated Jun 2016, Duralgina, Dvorah, Endocet, Esgic, Exaprin, Excedrin, Excedrin PM Triple Action, Excedrin Tension Headache, Feverall, Fioricet, Fioricet With Codeine, Goody\'s Back & Body Pain Relief, Goody\'s Body Pain, Goody\'s Extra Strength, Goody\'s ','Acetaminophen','<p>Acetaminophen (paracetamol), also commonly known as <em>Tylenol</em>, is the most commonly taken analgesic worldwide and is recommended as first-line therapy in pain conditions by the World Health Organization (WHO).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ennis ZN, Dideriksen D, Vaegter HB, Handberg G, Pottegard A: Acetaminophen for Chronic Pain: A Systematic Review on Efficacy. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):184-9. doi: 10.1111/bcpt.12527. Epub 2015 Dec 28. (PubMed ID 26572078)\" href=\"#reference-A176318\">10</a></sup> It is also used for its antipyretic effects, helping to reduce fever.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Acetaminophen monograph, suppository\" href=\"#reference-F4124\">23</a></sup> This drug was initially approved by the U.S. FDA in 1951 and is available in a variety of forms including syrup form, regular tablets, effervescent tablets, injection, suppository, and other forms.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Acetaminophen tablet, DailyMed\" href=\"#reference-L5756\">15</a>,<a class=\"reference-popover-link\" data-content=\"Acetaminophen effervescent tablets, Cleveland Clinic\" href=\"#reference-L5774\">16</a>,<a class=\"reference-popover-link\" data-content=\"Acetaminophen monograph, suppository\" href=\"#reference-F4124\">23</a>,<a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>Acetaminophen is often found combined with other drugs in more than 600 over the counter (OTC) allergy medications, cold medications, sleep medications, pain relievers, and other products.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA consumer health information: Acetaminophen\" href=\"#reference-L5783\">19</a></sup> Confusion about dosing of this drug may be caused by the availability of different formulas, strengths, and dosage instructions for children of different ages.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA consumer health information: Acetaminophen\" href=\"#reference-L5783\">19</a></sup> Due to the possibility of fatal overdose and liver failure associated with the incorrect use of acetaminophen, it is important to follow current and available national and manufacturer dosing guidelines while this drug is taken or prescribed.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA : Acetaminophen Information\" href=\"#reference-L5786\">20</a>,<a class=\"reference-popover-link\" data-content=\"Using Acetaminophen and Nonsteroidal Anti-inflammatory Drugs Safely\" href=\"#reference-L5789\">21</a>,<a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p>','C8H9NO2','DB00316','Approved','Small Molecule','Average: 151.1626 Monoisotopic: 151.063328537 ','N02BE71 — Paracetamol, combinations with psycholepticsN02BE — AnilidesN02B — OTHER ANALGESICS AND ANTIPYRETICSN02 — ANALGESICSN — NERVOUS SYSTEMN02BE01 — ParacetamolN02BE — AnilidesN02B — OTHER ANALGESICS AND ANTIPYRETICSN02 — ANALGESICSN — NERVOUS SYSTEMN02AJ13 — Tramadol and paracetamolN02AJ — Opioids in combination with non-opioid analgesicsN02A — OPIOIDSN02 — ANALGESICSN — NERVOUS SYSTEMN02AJ17 — Oxycodone and paracetamolN02AJ — Opioids in combination with non-opioid analgesicsN02A — OPIOIDSN02 — ANALGESICSN — NERVOUS SYSTEMN02BE51 — Paracetamol, combinations excl. psycholepticsN02BE — AnilidesN02B — OTHER ANALGESICS AND ANTIPYRETICSN02 — ANALGESICSN — NERVOUS SYSTEMN02AJ06 — Codeine and paracetamolN02AJ — Opioids in combination with non-opioid analgesicsN02A — OPIOIDSN02 — ANALGESICSN — NERVOUS SYSTEMN02AJ01 — Dihydrocodeine and paracetamolN02AJ — Opioids in combination with non-opioid analgesicsN02A — OPIOIDSN02 — ANALGESICSN — NERVOUS SYSTEM','Acetaminophen has 88% oral bioavailability and reaches its highest plasma concentration 90 minutes after ingestion.9\nPeak blood levels of free acetaminophen are not reached until 3 hours after rectal administration of the suppository form of acetaminophen and the peak blood concentration is approximately 50% of the observed concentration after the ingestion of an equivalent oral dose (10-20 mcg/mL).23\nThe percentage of a systemically absorbed rectal dose of acetaminophen is inconsistent, demonstrated by major differences in the bioavailability of acetaminophen after a dose administered rectally. Higher rectal doses or an increased frequency of administration may be used to attain blood concentrations of acetaminophen similar to those attained after oral acetaminophen administration.Label \n','Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Learn more  Improve decision support & research outcomes with our structured adverse effects data.Learn more','Humans and other mammals','Benzene and substituted derivatives / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives','Not Available','Not Available','26197','103-90-2','46195','CHEMBL112','1906','DescriptionThis compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.KingdomOrganic compoundsSuper ClassBenzenoidsClassPhenolsSub Class1-hydroxy-2-unsubstituted benzenoidsDirect Parent1-hydroxy-2-unsubstituted benzenoidsAlternative ParentsBenzene and substituted derivatives / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivativesSubstituents1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compoundMolecular FrameworkAromatic homomonocyclic compoundsExternal Descriptorsphenols, acetamides (CHEBI:46195)  / a small molecule (CPD-7669) ','Phenols','Adults: 0.27 L/h/kg following a 15 mg/kg intravenous (IV) dose.Label\nChildren: 0.34 L/h/kg following a 15 mg/kg intravenous (IV dose).Label\n','This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.','1-hydroxy-2-unsubstituted benzenoids','Avoid alcohol. Alcohol may increase the risk of hepatotoxicity.\nTake with or without food. The absorption is unaffected by food.','Drugs.com Drug Page','Acetaminophen and Prodrugs\nAmides\nAmines\nAnalgesics\nAnalgesics, Non-Narcotic\nAnilides\nAniline Compounds\nAntipyretics\nCentral Nervous System Agents\nCytochrome P-450 CYP1A2 Substrates\nCytochrome P-450 CYP2A6 Substrates\nCytochrome P-450 CYP2D6 Substrates\nCytochrome P-450 CYP2E1 Substrates\nCytochrome P-450 CYP3A Inducers\nCytochrome P-450 CYP3A Inhibitors\nCytochrome P-450 CYP3A Substrates\nCytochrome P-450 CYP3A4 Inducers\nCytochrome P-450 CYP3A4 Inducers (strength unknown)\nCytochrome P-450 CYP3A4 Inhibitors\nCytochrome P-450 CYP3A4 Inhibitors (weak)\nCytochrome P-450 CYP3A4 Substrates\nCytochrome P-450 Enzyme Inducers\nCytochrome P-450 Enzyme Inhibitors\nCytochrome P-450 Substrates\nDrugs that are Mainly Renally Excreted\nMethemoglobinemia Associated Agents\nMiscellaneous Analgesics and Antipyretics\nNervous System\nP-glycoprotein inhibitors\nP-glycoprotein substrates\nSensory System Agents\nUGT1A1 Substrates\nUGT1A6 substrate\nUGT1A9 Substrates','PropertyValueSourcemelting point (°C)170MSDSboiling point (°C)>500http://www.inchem.org/documents/icsc/icsc/eics1330.htmwater solubilityvery slightly soluble in cold water but greater solubility in hot waterhttp://www.inchem.org/documents/pims/pharm/pim396.htmlogP0.91http://www.t3db.ca/toxins/T3D2571logS-1.6http://www.t3db.ca/toxins/T3D2571pKa-4.4 (strongest basic)http://www.t3db.ca/toxins/T3D2571','phenols, acetamides (CHEBI:46195)  / a small molecule (CPD-7669) ','Human Metabolome DatabaseHMDB0001859KEGG DrugD00217KEGG CompoundC06804PubChem Compound1983PubChem Substance46506142ChemSpider1906BindingDB26197RxNav161ChEBI46195ChEMBLCHEMBL112ZINCZINC000013550868Therapeutic Targets DatabaseDAP001436PharmGKBPA448015PDBe LigandTYLRxListRxList Drug PageDrugs.comDrugs.com Drug PageWikipediaParacetamol','Avoid alcohol. Alcohol may increase the risk of hepatotoxicity.\nTake with or without food. The absorption is unaffected by food.','Kis B, Snipes JA, Busija DW: Acetaminophen and the cyclooxygenase-3 puzzle: sorting out facts, fictions, and uncertainties. J Pharmacol Exp Ther. 2005 Oct;315(1):1-7. Epub 2005 May 6. [Article] Aronoff DM, Oates JA, Boutaud O: New insights into the mechanism of action of acetaminophen: Its clinical pharmacologic characteristics reflect its inhibition of the two prostaglandin H2 synthases. Clin Pharmacol Ther. 2006 Jan;79(1):9-19. [Article] Bertolini A, Ferrari A, Ottani A, Guerzoni S, Tacchi R, Leone S: Paracetamol: new vistas of an old drug. CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75. [Article] Graham GG, Scott KF: Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55. [Article] Ohki S, Ogino N, Yamamoto S, Hayaishi O: Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. J Biol Chem. 1979 Feb 10;254(3):829-36. [Article] Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31. Epub 2002 Sep 19. [Article] Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article] Hazai E, Vereczkey L, Monostory K: Reduction of toxic metabolite formation of acetaminophen. Biochem Biophys Res Commun. 2002 Mar 8;291(4):1089-94. [Article] Mazaleuskaya LL, Sangkuhl K, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. doi: 10.1097/FPC.0000000000000150. [Article] Ennis ZN, Dideriksen D, Vaegter HB, Handberg G, Pottegard A: Acetaminophen for Chronic Pain: A Systematic Review on Efficacy. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):184-9. doi: 10.1111/bcpt.12527. Epub 2015 Dec 28. [Article] Bannwarth B, Pehourcq F: [Pharmacologic basis for using paracetamol: pharmacokinetic and pharmacodynamic issues]. Drugs. 2003;63 Spec No 2:5-13. [Article] Forrest JA, Clements JA, Prescott LF: Clinical pharmacokinetics of paracetamol. Clin Pharmacokinet. 1982 Mar-Apr;7(2):93-107. [Article] Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [Article] Valerie Gerriets; Thomas M. Nappe (2019). Acetaminophen. StatPearls publishing. Acetaminophen tablet, DailyMed [Link] Acetaminophen effervescent tablets, Cleveland Clinic [Link] FDA safety communication: FDA has reviewed possible risks of pain medicine use during pregnancy [Link] U.S. National Medical Library: MedlinePlus- Acetaminophen dosing for children [Link] FDA consumer health information: Acetaminophen [Link] FDA : Acetaminophen Information [Link] Using Acetaminophen and Nonsteroidal Anti-inflammatory Drugs Safely [Link] FDA Approved Drug Products: Acetaminophen solution for intravenous injection [Link] Acetaminophen monograph, suppository [File] Acetaminophen data sheet, ebi.ac.uk [File] Tylenol arthritis pain label, OTC [File] ','The half-life for adults is 2.5 h after an intravenous dose of 15 mg/kg.Label After an overdose, the half-life can range from 4 to 8 hours depending on the severity of injury to the liver, as it heavily metabolizes acetaminophen.9\n','HMDB0001859','N-(4-hydroxyphenyl)acetamide','InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)','RZVAJINKPMORJF-UHFFFAOYSA-N','In general, acetaminophen is used for the treatment of mild to moderate pain and reduction of fever.23 It is available over the counter in various forms, the most common being oral forms.\nAcetaminophen injection is indicated for the management of mild to moderate pain, the management of moderate to severe pain with adjunctive opioid analgesics, and the reduction of fever.Label\nBecause of its low risk of causing allergic reactions, this drug can be administered in patients who are intolerant to salicylates and those with allergic tendencies, including bronchial asthmatics.23 Specific dosing guidelines should be followed when administering acetaminophen to children.18\nReduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.See how  Build, train, & validate predictive machine-learning models with structured datasets.See how','C06804','D00217','Organic compounds','Acetaminophen is the major metabolite of phenacetin and acetanilid.23 Acetaminophen is mainly metabolized in the liver by first-order kinetics and its metabolism of comprised of 3 pathways: conjugation with glucuronide, conjugation with sulfate, and oxidation through the cytochrome P450 enzyme pathway, mainly CYP2E1, to produce a reactive metabolite (N-acetyl-p-benzoquinone imine or NAPQI). At normal therapeutic doses, NAPQI undergoes fast conjugation with glutathione and is subsequently metabolized to produce both cysteine and mercapturic acid conjugates.Label\nHigh doses of acetaminophen (overdoses) can lead to hepatic necrosis due to the depletion of glutathione and of binding of high levels of reactive metabolite (NAPQI) to important parts of liver cells. The abovementioned damage to the liver can be prevented by the early administration of sulfhydryl compounds, for example, methionine and N-acetylcysteine.12\nHover over products below to view reaction partnersAcetaminophen\n\n\nNAPQI\n\n\nAcetaminophen cysteine\n\n\nAcetaminophen glucuronide\n\n\nAcetaminophen sulfate','Aromatic homomonocyclic compounds','TYL','PathwayCategoryAcetaminophen Metabolism PathwayDrug metabolismAcetaminophen Action PathwayDrug action','PA448015','The binding of acetaminophen to plasma proteins is low (ranging from 10% to 25%), when given at therapeutic doses.Label\n','1983','46506142','Acetaminophen metabolites are mainly excreted in the urine. Less than 5% is excreted in the urine as free (unconjugated) acetaminophen and at least 90% of the administered dose is excreted within 24 hours.23\n','RxList Drug Page','161','CC(=O)NC1=CC=C(O)C=C1','Solid','1-hydroxy-2-unsubstituted benzenoids','1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound','Benzenoids','Jeffrey L. Finnan, Rudolph E. Lisa, Douglass N. Schmidt, \"Process for preparing spray dried acetaminophen powder and the powder prepared thereby.\" U.S. Patent US4710519, issued October, 1975.\nUS4710519','DAP001436','LD50 = 338 mg/kg (oral, mouse); LD50 = 1944 mg/kg (oral, rat)24\nOverdose and liver toxicity \nAcetaminophen overdose may be manifested by renal tubular necrosis, hypoglycemic coma, and thrombocytopenia. Sometimes, liver necrosis can occur as well as liver failure. Death and the requirement of a liver transplant may also occur.Label Metabolism by the CYP2E1 pathway releases a toxic acetaminophen metabolite known as N-acetyl-p-benzoquinoneimine(NAPQI). The toxic effects caused by this drug are attributed to NAPQI, not acetaminophen alone.24\nCarcinogenesis\nLong-term studies in mice and rats have been completed by the National Toxicology Program to study the carcinogenic risk of acetaminophen. In 2-year feeding studies, F344/N rats and B6C3F1 mice consumed a diet containing acetaminophen up to 6,000 ppm. Female rats showed evidence of carcinogenic activity demonstrated by a higher incidence of mononuclear cell leukemia at doses 0.8 times the maximum human daily dose (MHDD). No evidence of carcinogenesis in male rats (0.7 times) or mice (1.2 to 1.4 times the MHDD) was noted.Label The clinical relevance of this finding in humans is unknown.\nMutagenesis\nAcetaminophen was not found to be mutagenic in the bacterial reverse mutation assay (Ames test). Despite this finding, acetaminophen tested positive in the in vitro mouse lymphoma assay as well as the in vitro chromosomal aberration assay using human lymphocytes. In published studies, acetaminophen has been reported to be clastogenic (disrupting chromosomes) when given a high dose of 1,500 mg/kg/day to the rat model (3.6 times the MHDD). No clastogenicity was observed at a dose of 750 mg/kg/day (1.8 times the MHDD), indicating that this drug has a threshold before it may cause mutagenesis.Label The clinical relevance of this finding in humans is unknown.\nImpairment of Fertility\nIn studies conducted by the National Toxicology Program, fertility assessments have been performed in Swiss mice in a continuous breeding study. No effects on fertility were seen.Label \nUse in pregnancy and nursing\nThe FDA label for acetaminophen considers it a pregnancy category C drug, meaning this drug has demonstrated adverse effects in animal studies. No human clinical studies in pregnancy have been done to this date for intravenous acetaminophen.Label Use acetaminophen only when necessary during pregnancy.Label Epidemiological data on oral acetaminophen use in pregnant women demonstrate no increase in the risk of major congenital malformations.Label While prospective clinical studies examining the results of nursing with acetaminophen use have not been conducted, acetaminophen is found secreted in human milk at low concentrations after oral administration. Data from more than 15 nursing mothers taking acetaminophen was obtained, and the calculated daily dose of acetaminophen that reaches the infant is about 1 to 2% of the maternal dose. Caution should be observed when acetaminophen is taken by a nursing woman.Label\n','362O9ITL9D','Volume of distribution is about 0.9L/kg. 10 to 20% of the drug is bound to red blood cells.11 Acetaminophen appears to be widely distributed throughout most body tissues except in fat.Label\n','Paracetamol','ZINC000013550868'),(16,'Vitamin C','vitamin-c','Vitamin C is a vitamin used to correct vitamin C deficiency and to increase the intestinal absorption of iron.','Ascor, Citranatal B-calm Kit, Concept Ob, Ferralet 90, Ferraplus, Hematogen, Infuvite, Infuvite Pediatric, Moviprep, Mvc-fluoride, Mvi Pediatric, Natafort, Plenvu, Pregvit, Vitafol-one','Ascorbic acidCommonly known or available as Vitamin C','<p>A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.</p>','C6H8O6','DB00126','Approved, Nutraceutical','Small Molecule','Average: 176.1241 Monoisotopic: 176.032087988 ',' , G01AD — Organic acids , G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS , G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS , G — GENITO URINARY SYSTEM AND SEX HORMONES , A11GA — Ascorbic acid (vitamin C), plain , A11G — ASCORBIC ACID (VITAMIN C), INCL. COMBINATIONS , A11 — VITAMINS , A — ALIMENTARY TRACT AND METABOLISM , A11GB — Ascorbic acid (vitamin C), combinations , A11G — ASCORBIC ACID (VITAMIN C), INCL. COMBINATIONS , A11 — VITAMINS , A — ALIMENTARY TRACT AND METABOLISM , S01XA — Other ophthalmologicals , S01X — OTHER OPHTHALMOLOGICALS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS','<p>70% to 90%</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"An alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003626\" rel=\"noopener\" target=\"_blank\">Enoate esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enediol functional group, with the formula HO(R)C=C(R\')OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000131\" rel=\"noopener\" target=\"_blank\">Enediols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polyols containing an alcohol group at two adjacent positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002467\" rel=\"noopener\" target=\"_blank\">1,2-diols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 2 more</a>','Not Available','Not Available','50090256','50-81-7','29073','CHEMBL196','10189562','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001983\" rel=\"noopener\" target=\"_blank\">Dihydrofurans</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a furan ring bearing a ketone group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001982\" rel=\"noopener\" target=\"_blank\">Furanones</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Dihydrofurans with a carbonyl group at the C2 carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002223\" rel=\"noopener\" target=\"_blank\">Butenolides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"An alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003626\" rel=\"noopener\" target=\"_blank\">Enoate esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enediol functional group, with the formula HO(R)C=C(R\')OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000131\" rel=\"noopener\" target=\"_blank\">Enediols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polyols containing an alcohol group at two adjacent positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002467\" rel=\"noopener\" target=\"_blank\">1,2-diols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 2 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-diol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">2-furanone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha,beta-unsaturated carboxylic ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enediol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enoate ester</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">ascorbic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:29073\" rel=\"noopener\" target=\"_blank\">CHEBI:29073</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Water-soluble vitamins (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00072\" rel=\"noopener\" target=\"_blank\">C00072</a>) </span></span></dd></dl>','Dihydrofurans','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.','Butenolides','<li>Avoid multivalent ions. Do not infuse with elemental compounds that can be reduced, such as copper.</li>','Drugs.com Drug Page',' , Acids, Acyclic , Alimentary Tract and Metabolism , Antioxidants , Biological Factors , Carbohydrates , Compounds used in a research, industrial, or household setting , Diet, Food, and Nutrition , Food , Gastrointestinal Acidifying Agents , Genito Urinary System and Sex Hormones , Growth Substances , Gynecological Antiinfectives and Antiseptics , Hydroxy Acids , Micronutrients , Ophthalmologicals , Organic Acids , Physiological Phenomena , Protective Agents , Sensory Organs , Sugar Acids , Urinary Acidifying Agents , Vitamin C and analogues , Vitamins','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>191 dec °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>4E+005 mg/L (at 40 °C)</td><td>MERCK INDEX (1996)</td></tr><tr><td>logP</td><td>-1.85</td><td>AVDEEF,A (1997)</td></tr><tr><td>pKa</td><td>4.7 (at 10 °C)</td><td>KORTUM,G ET AL (1961)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">ascorbic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:29073\" rel=\"noopener\" target=\"_blank\">CHEBI:29073</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Water-soluble vitamins (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00072\" rel=\"noopener\" target=\"_blank\">C00072</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0000044\" rel=\"noopener\" target=\"_blank\">HMDB0000044</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00018\" rel=\"noopener\" target=\"_blank\">D00018</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00072\" rel=\"noopener\" target=\"_blank\">C00072</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=54670067\" rel=\"noopener\" target=\"_blank\">54670067</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505070\" rel=\"noopener\" target=\"_blank\">46505070</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.10189562.html\" rel=\"noopener\" target=\"_blank\">10189562</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50090256\" rel=\"noopener\" target=\"_blank\">50090256</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=1151\" rel=\"noopener\" target=\"_blank\">1151</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=29073\" rel=\"noopener\" target=\"_blank\">29073</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL196\" rel=\"noopener\" target=\"_blank\">CHEMBL196</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000100006770\" rel=\"noopener\" target=\"_blank\">ZINC000100006770</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DNC000259\" rel=\"noopener\" target=\"_blank\">DNC000259</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451898\" rel=\"noopener\" target=\"_blank\">PA451898</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/ASC\" rel=\"noopener\" target=\"_blank\">ASC</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic3/vitamc.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/ascorbic-acid.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0264.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Vitamin_C\" rel=\"noopener\" target=\"_blank\">Vitamin_C</a></dd></dl>','<li>Avoid multivalent ions. Do not infuse with elemental compounds that can be reduced, such as copper.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A7280\">Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M: Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr. 2003 Feb;22(1):18-35. [<a href=\"/articles/A7280\" target=\"_blank\">Article</a>] </li><li id=\"reference-A7281\">Meister A: Glutathione-ascorbic acid antioxidant system in animals. J Biol Chem. 1994 Apr 1;269(13):9397-400. [<a href=\"/articles/A7281\" target=\"_blank\">Article</a>] </li><li id=\"reference-A7282\">Englard S, Seifter S: The biochemical functions of ascorbic acid. Annu Rev Nutr. 1986;6:365-406. [<a href=\"/articles/A7282\" target=\"_blank\">Article</a>] </li><li id=\"reference-A7283\">Banhegyi G, Mandl J: The hepatic glycogenoreticular system. Pathol Oncol Res. 2001;7(2):107-10. [<a href=\"/articles/A7283\" target=\"_blank\">Article</a>] </li><li id=\"reference-A7284\">Proctor P: Similar functions of uric acid and ascorbate in man? Nature. 1970 Nov 28;228(5274):868. [<a href=\"/articles/A7284\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14571\">Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [<a href=\"/articles/A14571\" target=\"_blank\">Article</a>] </li><li id=\"reference-L12210\">FDA Approved Drug Products: Ascor Ascorbic Acid Intravenous Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209112s000lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>16 days (3.4 hours in people who have excess levels of vitamin C)</p>','HMDB0000044','(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one','InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1','CIWBSHSKHKDKBQ-JLAZNSOCSA-N','<p>Used to treat vitamin C deficiency, scurvy, delayed wound and bone healing, urine acidification, and in general as an antioxidant. It has also been suggested to be an effective antiviral agent.</p>','C00072','D00018','Organic compounds','<p>Hepatic. Ascorbic acid is reversibly oxidised (by removal of the hydrogen from the enediol group of ascorbic acid) to dehydroascorbic acid. The two forms found in body fluids are physiologically active. Some ascorbic acid is metabolized to inactive compounds including ascorbic acid-2-sulfate and oxalic acid.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteromonocyclic compounds','ASC','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000030?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Oxidation of Branched-Chain Fatty Acids</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000170?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Aromatic L-Aminoacid Decarboxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0002295?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">The Oncogenic Action of Fumarate</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000006?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Tyrosine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000012?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Catecholamine Biosynthesis</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000218?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Tyrosinemia Type I</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000429?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Disulfiram Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000450?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Phytanic Acid Peroxisomal Oxidation</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000465?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Carnitine Synthesis</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0002292?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">The Oncogenic Action of Succinate</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000169?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Alkaptonuria</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000190?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Hawkinsinuria</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000451?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Refsum Disease</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000494?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Tyrosinemia, Transient, of the Newborn</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000497?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Tyrosine Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000498?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Dopamine beta-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000533?highlight[compounds][]=DB00126&amp;highlight[proteins][]=DB00126\">Monoamine Oxidase-A Deficiency (MAO-A)</a></td><td>Disease</td></tr></tbody>','PA451898','<p>25%</p>','54670067','46505070','<p><span class=\"not-available\">Not Available</span></p>','RxList Drug Page','1151','[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO','Solid','Furanones','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-diol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">2-furanone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha,beta-unsaturated carboxylic ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enediol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enoate ester</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Lewis D. Morse, Paul A. Hammes, \"Beverage containing stabilized vitamin C and iron and method of making same.\" U.S. Patent US3958017, issued October, 1972.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=3958017&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US3958017</a>','DNC000259','<p><span class=\"not-available\">Not Available</span></p>','PQ6CK8PD0R','<p><span class=\"not-available\">Not Available</span></p>','Vitamin_C','ZINC000100006770'),(17,'Nicotine','nicotine','Nicotine is a stimulatory alkaloid found in tobacco products that is often used for the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.','Habitrol, Nicoderm C-Q, Nicorelief, Nicorette, Nicotrol','Nicotine','<p>Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.</p>','C10H14N2','DB00184','Approved','Small Molecule','Average: 162.2316 Monoisotopic: 162.115698458 ',' , N07BA — Drugs used in nicotine dependence , N07B — DRUGS USED IN ADDICTIVE DISORDERS , N07 — OTHER NERVOUS SYSTEM DRUGS , N — NERVOUS SYSTEM','<p>Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003449\" rel=\"noopener\" target=\"_blank\">N-alkylpyrrolidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span>','Not Available','Not Available','82070','54-11-5','17688','CHEMBL3','80863','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001975\" rel=\"noopener\" target=\"_blank\">Pyrrolidinylpyridines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001975\" rel=\"noopener\" target=\"_blank\">Pyrrolidinylpyridines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003449\" rel=\"noopener\" target=\"_blank\">N-alkylpyrrolidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkaloid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-alkylpyrrolidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">nicotine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17688\" rel=\"noopener\" target=\"_blank\">CHEBI:17688</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pesticides, Pyridine alkaloids, Alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00745\" rel=\"noopener\" target=\"_blank\">C00745</a>) </span></span></dd></dl>','Pyridines and derivatives','','This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.','Pyrrolidinylpyridines','<li>Take separate from meals. For nicotine gum, lozenges, and oral sprays, avoid eating and drinking for 15 minutes before and during its use.</li>','Drugs.com Drug Page',' , Agents producing tachycardia , Alkaloids , Autonomic Agents , Cholinergic Agents , Cholinergic Agonists , Cholinergic Nicotinic Agonist , Cytochrome P-450 CYP1A2 Inducers , Cytochrome P-450 CYP1A2 Inducers (strength unknown) , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP2A6 Inhibitors , Cytochrome P-450 CYP2A6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2A6 Substrates , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP2E1 Inducers , Cytochrome P-450 CYP2E1 Inducers (strength unknown) , Cytochrome P-450 CYP2E1 Inhibitors , Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) , Cytochrome P-450 CYP2E1 Substrates , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs Used in Addictive Disorders , Drugs Used in Nicotine Dependence , Ganglion Blockers , Ganglionic Stimulants , Miscellaneous Autonomic Drugs , Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates , Nervous System , Neurotransmitter Agents , Nicotine, antagonists & inhibitors , Nicotinic Agonists , OCT1 inhibitors , OCT2 Inhibitors , Peripheral Nervous System Agents , Pyridines , Smoking Cessation Agents , Solanaceous Alkaloids','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>-79 °C</td><td>PhysProp</td></tr><tr><td>boiling point (°C)</td><td>247 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>1E+006 mg/L</td><td>SEIDELL,A (1941)</td></tr><tr><td>logP</td><td>1.17</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>0.79</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.71</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>8.5</td><td>http://www.surgeongeneral.gov/library/reports/50-years-of-progress/sgr50-chap-5.pdf</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">nicotine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17688\" rel=\"noopener\" target=\"_blank\">CHEBI:17688</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pesticides, Pyridine alkaloids, Alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00745\" rel=\"noopener\" target=\"_blank\">C00745</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0001934\" rel=\"noopener\" target=\"_blank\">HMDB0001934</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D03365\" rel=\"noopener\" target=\"_blank\">D03365</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00745\" rel=\"noopener\" target=\"_blank\">C00745</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=89594\" rel=\"noopener\" target=\"_blank\">89594</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506924\" rel=\"noopener\" target=\"_blank\">46506924</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.80863.html\" rel=\"noopener\" target=\"_blank\">80863</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=82070\" rel=\"noopener\" target=\"_blank\">82070</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=31765\" rel=\"noopener\" target=\"_blank\">31765</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17688\" rel=\"noopener\" target=\"_blank\">17688</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL3\" rel=\"noopener\" target=\"_blank\">CHEMBL3</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000000391812\" rel=\"noopener\" target=\"_blank\">ZINC000000391812</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000175\" rel=\"noopener\" target=\"_blank\">DAP000175</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450626\" rel=\"noopener\" target=\"_blank\">PA450626</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/NCT\" rel=\"noopener\" target=\"_blank\">NCT</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic2/nicotini.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/nicotine.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nic1292.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Nicotine\" rel=\"noopener\" target=\"_blank\">Nicotine</a></dd></dl>','<li>Take separate from meals. For nicotine gum, lozenges, and oral sprays, avoid eating and drinking for 15 minutes before and during its use.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A261\">Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [<a href=\"/articles/A261\" target=\"_blank\">Article</a>] </li><li id=\"reference-A262\">de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [<a href=\"/articles/A262\" target=\"_blank\">Article</a>] </li><li id=\"reference-A263\">de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [<a href=\"/articles/A263\" target=\"_blank\">Article</a>] </li><li id=\"reference-A264\">Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [<a href=\"/articles/A264\" target=\"_blank\">Article</a>] </li></ol>','<p>Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours</p>','HMDB0001934','3-[(2S)-1-methylpyrrolidin-2-yl]pyridine','InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1','SNICXCGAKADSCV-JTQLQIEISA-N','<p>For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.</p>','C00745','D03365','Organic compounds','<p>Primarily hepatic, cotinine is the primary metabolite.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','NCT','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000431?highlight[compounds][]=DB00184&amp;highlight[proteins][]=DB00184\">Nicotine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000628?highlight[compounds][]=DB00184&amp;highlight[proteins][]=DB00184\">Nicotine Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA450626','<p>Less than 5%</p>','89594','46506924','<p>About 10% of the nicotine absorbed is excreted unchanged in the urine.</p>','RxList Drug Page','31765','CN1CCC[C@H]1C1=CN=CC=C1','Liquid','Pyrrolidinylpyridines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkaloid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-alkylpyrrolidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span></span></span>','Organoheterocyclic compounds','<span class=\"citations\"><p>Charles G. Chavdarian, Edward B. Sanders, \"Process for the preparation of optically active nicotine analogs.\" U.S. Patent US4321387, issued September, 1959.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4321387&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4321387</a>','DAP000175','<p>Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD<sub>50</sub>= 24 mg/kg (orally in mice).</p>','6M3C89ZY6R','','Nicotine','ZINC000000391812'),(18,'Erythromycin','erythromycin','Erythromycin is a macrolide antibiotic used to treat and prevent a variety of bacterial infections.','Aktipak, Apo-Erythro-S, Benzamycin, E.E.S., Ery, Ery-tab, Eryc, Erygel, Eryped, Erythro, Erythrocin, Erythrocin Stearate','Erythromycin','<p>Erythromycin is a bacteriostatic antibiotic drug produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics which consists of <a href=\"https://go.drugbank.com/drugs/DB00207\">Azithromycin</a>, <a href=\"https://go.drugbank.com/drugs/DB01211\">Clarithromycin</a>, <a href=\"https://go.drugbank.com/drugs/DB06145\">Spiramycin</a> and others. It was originally discovered in 1952.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"NIH StatPearls: Erythromycin\" href=\"#reference-L5245\">20</a></sup> Erythromycin is widely used for treating a variety of infections, including those caused by gram-positive and gram-negative bacteria.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"NIH StatPearls: Erythromycin\" href=\"#reference-L5245\">20</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> It is available for administration in various forms, including intravenous, topical, and eye drop preparations.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"NIH StatPearls: Erythromycin\" href=\"#reference-L5245\">20</a></sup></p>','C37H67NO13','DB00199','Approved, Investigational, Vet approved','Small Molecule','Average: 733.9268 Monoisotopic: 733.461241235 ',' , J01FA — Macrolides , J01F — MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , D10AF — Antiinfectives for treatment of acne , D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE , D10 — ANTI-ACNE PREPARATIONS , D — DERMATOLOGICALS , S01AA — Antibiotics , S01A — ANTIINFECTIVES , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , D10AF — Antiinfectives for treatment of acne , D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE , D10 — ANTI-ACNE PREPARATIONS , D — DERMATOLOGICALS','<p>Orally administered erythromycin is readily absorbed. Food intake does not appear to exert effects on serum concentrations of erythromycin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Some interindividual variation exists in terms of erythromycin absorption, which may impact absorption to varying degrees.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> The Cmax of erythromycin is 1.8 mcg/L<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Wang LQ, Hu ZY, Yu Q, Guo X, Xiong J, Huang ZZ, Cheng ZN: [Pharmacokinetics of erythromycin stinoprate capsule]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2005 Apr;30(2):197-201. (PubMed ID 15898434)\" href=\"#reference-A180598\">15</a></sup> and the Tmax is 1.2 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kavi J, Webberley JM, Andrews JM, Wise R: A comparison of the pharmacokinetics and tissue penetration of spiramycin and erythromycin. J Antimicrob Chemother. 1988 Jul;22 Suppl B:105-10. doi: 10.1093/jac/22.supplement_b.105. (PubMed ID 3182434)\" href=\"#reference-A180607\">19</a></sup> The serum AUC of erythromycin after the administration of a 500mg oral dose was 7.3±3.9 mg.h/l in one pharmacokinetic study.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kavi J, Webberley JM, Andrews JM, Wise R: A comparison of the pharmacokinetics and tissue penetration of spiramycin and erythromycin. J Antimicrob Chemother. 1988 Jul;22 Suppl B:105-10. doi: 10.1093/jac/22.supplement_b.105. (PubMed ID 3182434)\" href=\"#reference-A180607\">19</a></sup> Erythromycin is well known for a bioavailability that is variable (18-45%) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Amsden GW: Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 1996 Jan-Feb;18(1):56-72; discussion 55. (PubMed ID 8851453)\" href=\"#reference-A174451\">6</a>,<a class=\"reference-popover-link\" data-content=\"Mather LE, Austin KL, Philpot CR, McDonald PJ: Absorption and bioavailability of oral erythromycin. Br J Clin Pharmacol. 1981 Aug;12(2):131-40. doi: 10.1111/j.1365-2125.1981.tb01191.x. (PubMed ID 7306427)\" href=\"#reference-A180595\">14</a></sup> after oral administration and its susceptibility to broken down under acidic conditions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. (PubMed ID 22083477)\" href=\"#reference-A174448\">5</a></sup></p>','','Enteric bacteria and other eubacteria\nStreptococcus pyogenes\nHaemophilus influenzae\nStaphylococcus aureus','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a lactone ring of at least twelve members.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000147\" rel=\"noopener\" target=\"_blank\">Macrolides and analogues</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsGlucose-6-phosphate 1-dehydrogenaseVilleurbanneNot Available1000_1002delACCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTorunNot Available1006A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSunderlandNot Available105_107delCATADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIwatsukiNot Available1081G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSerresNot Available1082C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTondelaNot Available1084_1101delCTGAACGAGCGCAAGGCCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLoma LindaNot Available1089C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAachenNot Available1089C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTenriNot Available1096A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMontpellierNot Available1132G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCalvo MackennaNot Available1138A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRileyNot Available1139T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOlomoucNot Available1141T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTomahNot Available1153T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLynwoodNot Available1154G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMadridNot Available1155C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIowa, Walter Reed, SpringfieldNot Available1156A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBeverly Hills, Genova, Iwate, Niigata, YamaguchiNot Available1160G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHartfordNot Available1162A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePrahaNot Available1166A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKrakowNot Available1175T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWisconsinNot Available1177C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNashville, Anaheim, PorticiNot Available1178G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAlhambraNot Available1180G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBariNot Available1187C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePuerto LimonNot Available1192G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCovao do LoboNot Available1205C>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseClinicNot Available1215G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUtrechtNot Available1225C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSuwalkiNot Available1226C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRiversideNot Available1228G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseJapan, ShinagawaNot Available1229G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKawasakiNot Available1229G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMunichNot Available1231A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGeorgiaNot Available1284C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSumareNot Available1292T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTelti/KobeNot Available1318C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSantiago de Cuba, MoriokaNot Available1339G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHarimaNot Available1358T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFiguera da FozNot Available1366G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmiensNot Available1367A>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBangkok NoiNot Available1376G->T, 1502T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFukayaNot Available1462G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCampinasNot Available1463G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBuenos AiresNot Available1465C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseArakawaNot Available1466C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBrightonNot Available1488_1490delGAAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKozukataNot Available159G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmsterdamNot Available180_182delTCTADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNo nameNot Available202G->A, 376A->G, 1264C>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSwanseaNot Available224T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUrayasuNot Available281_283delAGAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVancouverNot Available317C->G544C->T592C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMt SinaiNot Available376A->G, 1159C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePlymouthNot Available488G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVolendamNot Available514C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseShinshuNot Available527A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChikugoNot Available535A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTsukuiNot Available561_563delCTCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePedoplis-CkaroNot Available573C>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSantiagoNot Available593G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMinnesota, Marion, Gastonia, LeJeuneNot Available637G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCincinnatiNot Available637G->T, 1037A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHarilaouNot Available648T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNorth DallasNot Available683_685delACAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAsahikawaNot Available695G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseDurhamNot Available713A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseStonybrookNot Available724_729delGGCACTADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWayneNot Available769C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAveiroNot Available806G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCleveland CorumNot Available820G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLilleNot Available821A>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBangkokNot Available825G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSugaoNot Available826C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLa JollaNot Available832T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWexhamNot Available833C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePiotrkowNot Available851T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWest VirginiaNot Available910G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOmiyaNot Available921G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNaraNot Available953_976delCCACCAAAGGGTACCTGGAC GACCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseManhattanNot Available962G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRehevotNot Available964T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHoniaraNot Available99A->G / 1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTokyo, FukushimaNot Available1246G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChathamNot Available1003G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFushanNot Available1004C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePartenopeNot Available1052G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIerapetraNot Available1057C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAnadiaNot Available1193A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAbenoNot Available1220A->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSurabayaNot Available1291G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePawneeNot Available1316G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseS. AntiocoNot Available1342A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCassanoNot Available1347G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHermoupolisNot Available1347G->C / 1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUnion,Maewo, Chinese-2, KaloNot Available1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAndalusNot Available1361G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCosenzaNot Available1376G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCanton, Taiwan- Hakka, Gifu-like, Agrigento-likeNot Available1376G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFloresNot Available1387C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKaiping, Anant, Dhon, Sapporo-like, WoseraNot Available1388G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKamogawaNot Available169C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCostanzoNot Available179T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmazoniaNot Available185C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSongklanagarindNot Available196T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHechiNot Available202G->A / 871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNamouruNot Available208T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBao LocNot Available352T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCrispimNot Available375G->T, 379G->T383T->C384C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAcrokorinthosNot Available376A->G / 463C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSanta MariaNot Available376A->G / 542A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAnanindeuaNot Available376A->G / 871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVanua LavaNot Available383T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseValladolidNot Available406C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBelemNot Available409C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLiuzhouNot Available442G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseShenzenNot Available473G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTaipei ‚ÄúChinese- 3‚ÄùNot Available493A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseToledoNot Available496C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNaoneNot Available497G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNankangNot Available517T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMiaoliNot Available519C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMediterranean, Dallas, Panama‚ Sassari, Cagliari, BirminghamNot Available563C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCoimbra ShundeNot Available592C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNilgiriNot Available593G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRadlowoNot Available679C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRoubaixNot Available811G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHaikouNot Available835A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChinese-1Not Available835A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMizushimaNot Available848A>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOsakaNot Available853C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseViangchan, JammuNot Available871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSeoulNot Available916G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLudhianaNot Available929G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFarroupilhaNot Available977C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChinese-5Not Available1024C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRignanoNot Available130G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOrissaNot Available131C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseG6PDNiceNot Available1380G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKamiube, KeelungNot Available1387C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNeapolisNot Available1400C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAuresNot Available143T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSplitNot Available1442C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKambosNot Available148C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePalestrinaNot Available170G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMetapontoNot Available172G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMusashinoNot Available185C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAsahiNot Available202G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (202), Ferrara INot Available202G->A / 376A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMurcia OristanoNot Available209A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUbe KonanNot Available241C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLagosantoNot Available242G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGuangzhouNot Available274C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHammersmithNot Available323T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSinnaiNot Available34G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (680)Not Available376A->G / 680G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (968), Betica,Selma, GuantanamoNot Available376A->G / 968T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSalerno PyrgosNot Available383T>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseQuing YanNot Available392G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLagesNot Available40G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIleshaNot Available466G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMahidolNot Available487G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMalagaNot Available542A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSibariNot Available634A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMexico CityNot Available680G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNanningNot Available703C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSeattle, Lodi, Modena, Ferrara II, Athens-likeNot Available844G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBajo MaumereNot Available844G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMontalbanoNot Available854G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKalyan-Kerala, Jamnaga, RohiniNot Available949G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGaoheNot Available95A->GADR InferredIncreased risk of dose-related hemolysis.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsGlucose-6-phosphate 1-dehydrogenaseVilleurbanneNot Available1000_1002delACCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTorunNot Available1006A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSunderlandNot Available105_107delCATADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIwatsukiNot Available1081G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSerresNot Available1082C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTondelaNot Available1084_1101delCTGAACGAGCGCAAGGCCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLoma LindaNot Available1089C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAachenNot Available1089C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTenriNot Available1096A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMontpellierNot Available1132G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCalvo MackennaNot Available1138A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRileyNot Available1139T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOlomoucNot Available1141T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTomahNot Available1153T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLynwoodNot Available1154G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMadridNot Available1155C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIowa, Walter Reed, SpringfieldNot Available1156A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBeverly Hills, Genova, Iwate, Niigata, YamaguchiNot Available1160G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHartfordNot Available1162A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePrahaNot Available1166A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKrakowNot Available1175T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWisconsinNot Available1177C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNashville, Anaheim, PorticiNot Available1178G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAlhambraNot Available1180G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBariNot Available1187C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePuerto LimonNot Available1192G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCovao do LoboNot Available1205C>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseClinicNot Available1215G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUtrechtNot Available1225C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSuwalkiNot Available1226C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRiversideNot Available1228G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseJapan, ShinagawaNot Available1229G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKawasakiNot Available1229G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMunichNot Available1231A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGeorgiaNot Available1284C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSumareNot Available1292T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTelti/KobeNot Available1318C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSantiago de Cuba, MoriokaNot Available1339G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHarimaNot Available1358T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFiguera da FozNot Available1366G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmiensNot Available1367A>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBangkok NoiNot Available1376G->T, 1502T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFukayaNot Available1462G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCampinasNot Available1463G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBuenos AiresNot Available1465C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseArakawaNot Available1466C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBrightonNot Available1488_1490delGAAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKozukataNot Available159G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmsterdamNot Available180_182delTCTADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNo nameNot Available202G->A, 376A->G, 1264C>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSwanseaNot Available224T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUrayasuNot Available281_283delAGAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVancouverNot Available317C->G544C->T592C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMt SinaiNot Available376A->G, 1159C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePlymouthNot Available488G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVolendamNot Available514C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseShinshuNot Available527A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChikugoNot Available535A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTsukuiNot Available561_563delCTCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePedoplis-CkaroNot Available573C>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSantiagoNot Available593G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMinnesota, Marion, Gastonia, LeJeuneNot Available637G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCincinnatiNot Available637G->T, 1037A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHarilaouNot Available648T->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNorth DallasNot Available683_685delACAADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAsahikawaNot Available695G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseDurhamNot Available713A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseStonybrookNot Available724_729delGGCACTADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWayneNot Available769C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAveiroNot Available806G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCleveland CorumNot Available820G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLilleNot Available821A>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBangkokNot Available825G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSugaoNot Available826C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLa JollaNot Available832T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWexhamNot Available833C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePiotrkowNot Available851T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseWest VirginiaNot Available910G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOmiyaNot Available921G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNaraNot Available953_976delCCACCAAAGGGTACCTGGAC GACCADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseManhattanNot Available962G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRehevotNot Available964T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHoniaraNot Available99A->G / 1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTokyo, FukushimaNot Available1246G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChathamNot Available1003G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFushanNot Available1004C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePartenopeNot Available1052G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIerapetraNot Available1057C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAnadiaNot Available1193A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAbenoNot Available1220A->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSurabayaNot Available1291G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePawneeNot Available1316G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseS. AntiocoNot Available1342A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCassanoNot Available1347G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHermoupolisNot Available1347G->C / 1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUnion,Maewo, Chinese-2, KaloNot Available1360C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAndalusNot Available1361G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCosenzaNot Available1376G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCanton, Taiwan- Hakka, Gifu-like, Agrigento-likeNot Available1376G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFloresNot Available1387C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKaiping, Anant, Dhon, Sapporo-like, WoseraNot Available1388G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKamogawaNot Available169C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCostanzoNot Available179T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAmazoniaNot Available185C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSongklanagarindNot Available196T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHechiNot Available202G->A / 871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNamouruNot Available208T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBao LocNot Available352T>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCrispimNot Available375G->T, 379G->T383T->C384C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAcrokorinthosNot Available376A->G / 463C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSanta MariaNot Available376A->G / 542A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAnanindeuaNot Available376A->G / 871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseVanua LavaNot Available383T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseValladolidNot Available406C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBelemNot Available409C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLiuzhouNot Available442G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseShenzenNot Available473G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseTaipei ‚ÄúChinese- 3‚ÄùNot Available493A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseToledoNot Available496C>TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNaoneNot Available497G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNankangNot Available517T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMiaoliNot Available519C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMediterranean, Dallas, Panama‚ Sassari, Cagliari, BirminghamNot Available563C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseCoimbra ShundeNot Available592C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNilgiriNot Available593G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRadlowoNot Available679C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRoubaixNot Available811G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHaikouNot Available835A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChinese-1Not Available835A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMizushimaNot Available848A>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOsakaNot Available853C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseViangchan, JammuNot Available871G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSeoulNot Available916G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLudhianaNot Available929G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseFarroupilhaNot Available977C->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseChinese-5Not Available1024C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseRignanoNot Available130G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseOrissaNot Available131C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseG6PDNiceNot Available1380G>CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKamiube, KeelungNot Available1387C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNeapolisNot Available1400C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAuresNot Available143T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSplitNot Available1442C->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKambosNot Available148C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenasePalestrinaNot Available170G>AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMetapontoNot Available172G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMusashinoNot Available185C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseAsahiNot Available202G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (202), Ferrara INot Available202G->A / 376A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMurcia OristanoNot Available209A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseUbe KonanNot Available241C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLagosantoNot Available242G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGuangzhouNot Available274C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseHammersmithNot Available323T->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSinnaiNot Available34G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (680)Not Available376A->G / 680G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseA- (968), Betica,Selma, GuantanamoNot Available376A->G / 968T->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSalerno PyrgosNot Available383T>GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseQuing YanNot Available392G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseLagesNot Available40G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseIleshaNot Available466G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMahidolNot Available487G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMalagaNot Available542A->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSibariNot Available634A->GADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMexico CityNot Available680G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseNanningNot Available703C->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseSeattle, Lodi, Modena, Ferrara II, Athens-likeNot Available844G->CADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseBajo MaumereNot Available844G->TADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseMontalbanoNot Available854G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseKalyan-Kerala, Jamnaga, RohiniNot Available949G->AADR InferredIncreased risk of dose-related hemolysis.DetailsGlucose-6-phosphate 1-dehydrogenaseGaoheNot Available95A->GADR InferredIncreased risk of dose-related hemolysis.Details','50344942','114-07-8','42355','CHEMBL532','12041','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain one or more oxygen atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004603\" rel=\"noopener\" target=\"_blank\">Organic oxygen compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Monosaccharides, disaccharides, oligosaccharides, polysaccharides, and their derivatives.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000011\" rel=\"noopener\" target=\"_blank\">Carbohydrates and carbohydrate conjugates</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Molecules or a portion of a molecule composed of amino-modified sugars.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000282\" rel=\"noopener\" target=\"_blank\">Aminoglycosides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a lactone ring of at least twelve members.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000147\" rel=\"noopener\" target=\"_blank\">Macrolides and analogues</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Macrolide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">erythromycin (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42355\" rel=\"noopener\" target=\"_blank\">CHEBI:42355</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides, Macrolides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01912\" rel=\"noopener\" target=\"_blank\">C01912</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK04000006\" rel=\"noopener\" target=\"_blank\">LMPK04000006</a>) </span></span></dd></dl>','Organooxygen compounds','<p>The clearance of erythromycin in healthy subjects was 0.53 ± 0.13 l/h/kg after a 125mg intravenous dose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sun H, Frassetto LA, Huang Y, Benet LZ: Hepatic clearance, but not gut availability, of erythromycin is altered in patients with end-stage renal disease. Clin Pharmacol Ther. 2010 Apr;87(4):465-72. doi: 10.1038/clpt.2009.247. Epub 2010 Jan 20. (PubMed ID 20090676)\" href=\"#reference-A174457\">11</a></sup> In a clinical study of healthy patients and patients with liver cirrhosis, clearance of erythromycin was significantly reduced in those with severe liver cirrhosis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Barre J, Mallat A, Rosenbaum J, Deforges L, Houin G, Dhumeaux D, Tillement JP: Pharmacokinetics of erythromycin in patients with severe cirrhosis. Respective influence of decreased serum binding and impaired liver metabolic capacity. Br J Clin Pharmacol. 1987 Jun;23(6):753-7. doi: 10.1111/j.1365-2125.1987.tb03111.x. (PubMed ID 3606934)\" href=\"#reference-A180604\">17</a></sup> The clearance in cirrhotic patients was 42.2 ± 10.1 l h–1 versus 113.2 ± 44.2 l h-1 in healthy patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Barre J, Mallat A, Rosenbaum J, Deforges L, Houin G, Dhumeaux D, Tillement JP: Pharmacokinetics of erythromycin in patients with severe cirrhosis. Respective influence of decreased serum binding and impaired liver metabolic capacity. Br J Clin Pharmacol. 1987 Jun;23(6):753-7. doi: 10.1111/j.1365-2125.1987.tb03111.x. (PubMed ID 3606934)\" href=\"#reference-A180604\">17</a></sup></p>','This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.','Aminoglycosides','<li>Avoid grapefruit products.</li>\n<li>Take on an empty stomach. Allow approximately 30 minutes to 2 hours before meals, as this increases erythromycin absorption.</li>\n<li>Take with a full glass of water.</li>','Drugs.com Drug Page',' , Anti-Acne Preparations , Anti-Acne Preparations for Topical Use , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antiinfectives for Systemic Use , Antiinfectives for Treatment of Acne , BSEP/ABCB11 Inhibitors , BSEP/ABCB11 Substrates , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (moderate) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Inhibitors , Cytochrome P-450 CYP3A5 Inhibitors (moderate) , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Inhibitors , Cytochrome P-450 CYP3A7 Inhibitors (moderate) , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dermatologicals , Enzyme Inhibitors , Erythromycin and similars , Erythromycins , Gastrointestinal Agents , Lactones , Macrolide Antimicrobial , Macrolides , Macrolides, Lincosamides and Streptogramins , Moderate Risk QTc-Prolonging Agents , OATP1B1/SLCO1B1 Inhibitors , OATP1B1/SLCO1B1 Substrates , OATP1B3 inhibitors , OATP1B3 substrates , Ophthalmologicals , P-glycoprotein inhibitors , P-glycoprotein substrates , Protein Synthesis Inhibitors , QTc Prolonging Agents','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>133-135 </td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx</td></tr><tr><td>boiling point (°C)</td><td>719.69</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx</td></tr><tr><td>water solubility</td><td>Soluble in water at 2mg/ml</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx</td></tr><tr><td>logP</td><td>2.6</td><td>http://www.t3db.ca/toxins/T3D4764</td></tr><tr><td>logS</td><td>-3.2</td><td>http://www.t3db.ca/toxins/T3D4764</td></tr><tr><td>pKa</td><td>8.88 </td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">erythromycin (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42355\" rel=\"noopener\" target=\"_blank\">CHEBI:42355</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides, Macrolides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01912\" rel=\"noopener\" target=\"_blank\">C01912</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK04000006\" rel=\"noopener\" target=\"_blank\">LMPK04000006</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014344\" rel=\"noopener\" target=\"_blank\">HMDB0014344</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00140\" rel=\"noopener\" target=\"_blank\">D00140</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01912\" rel=\"noopener\" target=\"_blank\">C01912</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560\" rel=\"noopener\" target=\"_blank\">12560</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487\" rel=\"noopener\" target=\"_blank\">46508487</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.12041.html\" rel=\"noopener\" target=\"_blank\">12041</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344942\" rel=\"noopener\" target=\"_blank\">50344942</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=4053\" rel=\"noopener\" target=\"_blank\">4053</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=42355\" rel=\"noopener\" target=\"_blank\">42355</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532\" rel=\"noopener\" target=\"_blank\">CHEMBL532</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000085534336\" rel=\"noopener\" target=\"_blank\">ZINC000085534336</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111\" rel=\"noopener\" target=\"_blank\">DAP000111</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA449493\" rel=\"noopener\" target=\"_blank\">PA449493</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/ERY\" rel=\"noopener\" target=\"_blank\">ERY</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/erithrom.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/erythromycin-ointment.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Erythromycin\" rel=\"noopener\" target=\"_blank\">Erythromycin</a></dd></dl>','<li>Avoid grapefruit products.</li>\n<li>Take on an empty stomach. Allow approximately 30 minutes to 2 hours before meals, as this increases erythromycin absorption.</li>\n<li>Take with a full glass of water.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A290\">Kanazawa S, Ohkubo T, Sugawara K: The effects of grapefruit juice on the pharmacokinetics of erythromycin. Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):799-803. [<a href=\"/articles/A290\" target=\"_blank\">Article</a>] </li><li id=\"reference-A291\">Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. [<a href=\"/articles/A291\" target=\"_blank\">Article</a>] </li><li id=\"reference-A292\">Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment period with erythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. [<a href=\"/articles/A292\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174445\">Houin G, Tillement JP, Lhoste F, Rapin M, Soussy CJ, Duval J: Erythromycin pharmacokinetics in man. J Int Med Res. 1980;8 Suppl 2:9-14. [<a href=\"/articles/A174445\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174448\">Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. [<a href=\"/articles/A174448\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174451\">Amsden GW: Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 1996 Jan-Feb;18(1):56-72; discussion 55. [<a href=\"/articles/A174451\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174454\">Gordon RC, Regamey C, Kirby WM: Serum protein binding of erythromycin, lincomycin, and clindamycin. J Pharm Sci. 1973 Jul;62(7):1074-7. [<a href=\"/articles/A174454\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174175\">Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. [<a href=\"/articles/A174175\" target=\"_blank\">Article</a>] </li><li id=\"reference-A6505\">Champney WS, Burdine R: Macrolide antibiotics inhibit 50S ribosomal subunit assembly in Bacillus subtilis and Staphylococcus aureus. Antimicrob Agents Chemother. 1995 Sep;39(9):2141-4. [<a href=\"/articles/A6505\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14179\">Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [<a href=\"/articles/A14179\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174457\">Sun H, Frassetto LA, Huang Y, Benet LZ: Hepatic clearance, but not gut availability, of erythromycin is altered in patients with end-stage renal disease. Clin Pharmacol Ther. 2010 Apr;87(4):465-72. doi: 10.1038/clpt.2009.247. Epub 2010 Jan 20. [<a href=\"/articles/A174457\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174460\">Franke RM, Lancaster CS, Peer CJ, Gibson AA, Kosloske AM, Orwick SJ, Mathijssen RH, Figg WD, Baker SD, Sparreboom A: Effect of ABCC2 (MRP2) transport function on erythromycin metabolism. Clin Pharmacol Ther. 2011 May;89(5):693-701. doi: 10.1038/clpt.2011.25. Epub 2011 Mar 30. [<a href=\"/articles/A174460\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174193\">Dinos GP: The macrolide antibiotic renaissance. Br J Pharmacol. 2017 Sep;174(18):2967-2983. doi: 10.1111/bph.13936. Epub 2017 Aug 10. [<a href=\"/articles/A174193\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180595\">Mather LE, Austin KL, Philpot CR, McDonald PJ: Absorption and bioavailability of oral erythromycin. Br J Clin Pharmacol. 1981 Aug;12(2):131-40. doi: 10.1111/j.1365-2125.1981.tb01191.x. [<a href=\"/articles/A180595\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180598\">Wang LQ, Hu ZY, Yu Q, Guo X, Xiong J, Huang ZZ, Cheng ZN: [Pharmacokinetics of erythromycin stinoprate capsule]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2005 Apr;30(2):197-201. [<a href=\"/articles/A180598\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180601\">Colburn WA, Di Santo AR, Gibaldi M: Pharmacokinetics of erythromycin on repetitive dosing. J Clin Pharmacol. 1977 Oct;17(10 Pt 1):592-600. [<a href=\"/articles/A180601\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180604\">Barre J, Mallat A, Rosenbaum J, Deforges L, Houin G, Dhumeaux D, Tillement JP: Pharmacokinetics of erythromycin in patients with severe cirrhosis. Respective influence of decreased serum binding and impaired liver metabolic capacity. Br J Clin Pharmacol. 1987 Jun;23(6):753-7. doi: 10.1111/j.1365-2125.1987.tb03111.x. [<a href=\"/articles/A180604\" target=\"_blank\">Article</a>] </li><li id=\"reference-A33081\">Periti P, Mazzei T, Mini E, Novelli A: Clinical pharmacokinetic properties of the macrolide antibiotics. Effects of age and various pathophysiological states (Part I). Clin Pharmacokinet. 1989 Apr;16(4):193-214. doi: 10.2165/00003088-198916040-00001. [<a href=\"/articles/A33081\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180607\">Kavi J, Webberley JM, Andrews JM, Wise R: A comparison of the pharmacokinetics and tissue penetration of spiramycin and erythromycin. J Antimicrob Chemother. 1988 Jul;22 Suppl B:105-10. doi: 10.1093/jac/22.supplement_b.105. [<a href=\"/articles/A180607\" target=\"_blank\">Article</a>] </li><li id=\"reference-L5245\">NIH StatPearls: Erythromycin [<a href=\"https://www.ncbi.nlm.nih.gov/books/NBK532249/\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7261\">FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050207s074,050611s036lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7270\">MedSafe NZ: ERA (erythromycin stearate) oral filmtabs [<a href=\"https://www.medsafe.govt.nz/Profs/Datasheet/e/ERAcaptab.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7279\">Pfizer: Erythromycin MSDS [<a href=\"https://www.pfizer.com/system/files/products/material_safety_data/PZ00645.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-F3343\">Erythromycin estolate monograph [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/343/original/Erythromycin_Estolate.pdf?1549406070\" target=\"_blank\">File</a>] </li></ol>','<p>The elimination half-life of oral erythromycin was 3.5 hours according to one study<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Amsden GW: Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 1996 Jan-Feb;18(1):56-72; discussion 55. (PubMed ID 8851453)\" href=\"#reference-A174451\">6</a></sup> and ranged between 2.4-3.1 hours in another study.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Wang LQ, Hu ZY, Yu Q, Guo X, Xiong J, Huang ZZ, Cheng ZN: [Pharmacokinetics of erythromycin stinoprate capsule]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2005 Apr;30(2):197-201. (PubMed ID 15898434)\" href=\"#reference-A180598\">15</a></sup> Repetitive dosing of erythromycin leads to increased elimination half-life.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Colburn WA, Di Santo AR, Gibaldi M: Pharmacokinetics of erythromycin on repetitive dosing. J Clin Pharmacol. 1977 Oct;17(10 Pt 1):592-600. (PubMed ID 915023)\" href=\"#reference-A180601\">16</a></sup> </p>','HMDB0014344','(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione','InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1','ULGZDMOVFRHVEP-RWJQBGPGSA-N','<p>Erythromycin is indicated in the treatment of infections caused by susceptible strains of various bacteria.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> The indications for erythromycin have been summarized by body system below:</p><p><strong>Respiratory infections</strong></p><p>Mild to moderate upper respiratory tract infections caused by Streptococcus pyogenes, Streptococcus pneumoniae, or Haemophilus influenzae (when used concomitantly with appropriate doses of sulfonamides) can be treated with erythromycin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Mild to moderate lower-respiratory tract infections due to susceptible strains of Streptococcus pneumoniae or Streptococcus pyogenes may also be treated. Erythromycin treats listeriosis caused by Listeria monocytogenes may also be treated with erythromycin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup>\nErythromycin is indicated to treat pertussis (whooping cough) caused by Bordetella pertussis. It is effective in eliminating the causative organism from the nasopharynx of infected individuals, rendering them noninfectious. Clinical studies suggest that erythromycin may aid in the prevention of pertussis infection for individuals who have been exposed to the bacteria.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Respiratory tract infections due to Mycoplasma pneumoniae may also be treated with erythromycin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Despite the fact that no controlled clinical efficacy studies have been conducted to this date, in vitro and certain preliminary clinical study results indicate that erythromycin may be an effective treatment in Legionnaires’ Disease.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Finally, erythromycin is indicated to treat diphtheria and other infections due to Corynebacterium diphtheriae, as an adjunct to antitoxin, to prevent carrier status and to eradicate the organism in existing carriers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> In addition to the prevention of diphtheria, erythromycin can be used to prevent rheumatic fever in penicillin intolerant patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p><p><strong>Skin infections</strong></p><p>Mild to moderate skin or skin structure infections caused by Streptococcus pyogenes or Staphylococcus aureus may be treated with erythromycin, however, resistant staphylococcal organisms may emerge.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Erythromycin can also be used to treat erythrasma, an infectious condition caused by Corynebacterium minutissimum.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p><p><strong>Gastrointestinal infections</strong></p><p>Intestinal amebiasis caused by Entamoeba histolytica can be treated with oral erythromycin. Extraenteric amebiasis warrants treatment with other antimicrobial drugs.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p><p><strong>Genital infections/STIs</strong></p><p>Erythromycin can be used as an alternative drug in treating acute pelvic inflammatory disease caused by N. gonorrheae in female patients who have demonstrated hypersensitivity or intolerance to penicillin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Syphilis, caused by Treponema pallidum, can be treated with erythromycin. It serves as an alternative treatment for primary syphilis in patients who have demonstrated penicillin hypersensitivity. Erythromycin can also be used in the primary stage of primary syphilis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Another approved indication of erythromycin is to treat chlamydial infections that cause conjunctivitis of the newborn, pneumonia of infancy, and urogenital infections occurring in pregnancy. It is indicated as an alternative option to tetracyclines for the treatment of uncomplicated rectal, urethral and endocervical infections in adults caused by Chlamydia trachomatis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup> Erythromycin can be used in nongonococcal urethritis can be used when tetracyclines cannot be administered. Finally, erythromycin is indicated to treat nongonococcal urethritis due to Ureaplasma urealyticum.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p>','C01912','D00140','Organic compounds','<p>Hepatic first-pass metabolism contributes significantly to erythromycin metabolism after an oral dose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sun H, Frassetto LA, Huang Y, Benet LZ: Hepatic clearance, but not gut availability, of erythromycin is altered in patients with end-stage renal disease. Clin Pharmacol Ther. 2010 Apr;87(4):465-72. doi: 10.1038/clpt.2009.247. Epub 2010 Jan 20. (PubMed ID 20090676)\" href=\"#reference-A174457\">11</a></sup> Erythromycin is partially metabolized by CYP3A4 enzyme to N-desmethylerythromycin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a>,<a class=\"reference-popover-link\" data-content=\"Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. (PubMed ID 28146011)\" href=\"#reference-A174175\">8</a></sup> Erythromycin is also hydrolyzed to <em>anhydro</em> forms (anhydroerythromycin [AHE] and other metabolites), and this process is promoted by acidic conditions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. (PubMed ID 22083477)\" href=\"#reference-A174448\">5</a></sup> AHE is inactive against microbes but inhibits hepatic drug oxidation and is therefore considered to be an important contributor to erythromycin drug-drug interactions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. (PubMed ID 22083477)\" href=\"#reference-A174448\">5</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteromonocyclic compounds','ERY','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000250?highlight[compounds][]=DB00199&amp;highlight[proteins][]=DB00199\">Erythromycin Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449493','<p>Erythromycin demonstrates 93% serum protein binding in the erythromycin propionate form.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gordon RC, Regamey C, Kirby WM: Serum protein binding of erythromycin, lincomycin, and clindamycin. J Pharm Sci. 1973 Jul;62(7):1074-7. (PubMed ID 4714113)\" href=\"#reference-A174454\">7</a></sup> Another resource indicates that erythromycin protein binding ranges from 80 to 90%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Periti P, Mazzei T, Mini E, Novelli A: Clinical pharmacokinetic properties of the macrolide antibiotics. Effects of age and various pathophysiological states (Part I). Clin Pharmacokinet. 1989 Apr;16(4):193-214. doi: 10.2165/00003088-198916040-00001. (PubMed ID 2656049)\" href=\"#reference-A33081\">18</a></sup></p>','12560','46508487','<p>In patients with normal liver function, erythromycin concentrates in the liver and is then excreted in the bile.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"MedSafe NZ: ERA (erythromycin stearate) oral filmtabs\" href=\"#reference-L7270\">22</a></sup>Under 5% of the orally administered dose of erythromycin is found excreted in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"MedSafe NZ: ERA (erythromycin stearate) oral filmtabs\" href=\"#reference-L7270\">22</a>,<a class=\"reference-popover-link\" data-content=\"Kavi J, Webberley JM, Andrews JM, Wise R: A comparison of the pharmacokinetics and tissue penetration of spiramycin and erythromycin. J Antimicrob Chemother. 1988 Jul;22 Suppl B:105-10. doi: 10.1093/jac/22.supplement_b.105. (PubMed ID 3182434)\" href=\"#reference-A180607\">19</a></sup> A high percentage of absorbed erythromycin is not accounted for, but is likely metabolized.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"MedSafe NZ: ERA (erythromycin stearate) oral filmtabs\" href=\"#reference-L7270\">22</a></sup></p>','RxList Drug Page','4053','CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O','Solid','Carbohydrates and carbohydrate conjugates','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Macrolide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a>','Organic oxygen compounds','<span class=\"citations\"><p>Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, \"Process for preparing erythromycin A oxime or a salt thereof.\" U.S. Patent US5274085, issued October, 1966.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5274085&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5274085</a>','DAP000111','<p>LD50</p><p>The oral LD50 of erythromycin in rats is 9272 mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pfizer: Erythromycin MSDS\" href=\"#reference-L7279\">23</a></sup></p><p>Overdose information</p><p>Symptoms of overdose may include diarrhea, nausea, stomach cramps, and vomiting. Erythromycin should immediately be discontinued in cases of overdose. Rapid elimination of unabsorbed drug should be attempted. Supportive measures should be initiated. Erythromycin is not adequately removed by peritoneal dialysis or hemodialysis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p>','63937KV33D','<p>Erythromycin is found in most body fluids and accumulates in leucocytes and inflammatory liquid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a>,<a class=\"reference-popover-link\" data-content=\"Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. (PubMed ID 22083477)\" href=\"#reference-A174448\">5</a>,<a class=\"reference-popover-link\" data-content=\"Kavi J, Webberley JM, Andrews JM, Wise R: A comparison of the pharmacokinetics and tissue penetration of spiramycin and erythromycin. J Antimicrob Chemother. 1988 Jul;22 Suppl B:105-10. doi: 10.1093/jac/22.supplement_b.105. (PubMed ID 3182434)\" href=\"#reference-A180607\">19</a></sup> Spinal fluid concentrations of erythromycin are low, however, the diffusion of erythromycin through the blood-brain barrier increases in meningitis, likely due to the presence of inflamed tissues which are easily penetrated.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"MedSafe NZ: ERA (erythromycin stearate) oral filmtabs\" href=\"#reference-L7270\">22</a></sup> Erythromycin crosses the placenta.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ery-Ped (erythromycin ethylsuccinate) granules for oral suspension\" href=\"#reference-L7261\">21</a></sup></p>','Erythromycin','ZINC000085534336'),(19,'Lovastatin','lovastatin','Lovastatin is an HMG-CoA reductase inhibitor used to lower LDL cholesterol and reduce the risk of cardiovascular disease and associated conditions, including myocardial infarction and stroke.','Advicor, Altoprev','Lovastatin','<p>Lovastatin, also known as the brand name product Mevacor, is a lipid-lowering drug and fungal metabolite derived synthetically from a fermentation product of <em>Aspergillus terreus</em>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Boruta T, Bizukojc M: Production of lovastatin and itaconic acid by Aspergillus terreus: a comparative perspective. World J Microbiol Biotechnol. 2017 Feb;33(2):34. doi: 10.1007/s11274-017-2206-9. Epub 2017 Jan 19. (PubMed ID 28102516)\" href=\"#reference-A174550\">1</a></sup> Originally named Mevinolin, lovastatin belongs to the statin class of medications, which are used to lower the risk of cardiovascular disease and manage abnormal lipid levels by inhibiting the endogenous production of cholesterol in the liver.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffman C, Rothrock J, Lopez M, Joshua H, Harris E, Patchett A, Monaghan R, Currie S, Stapley E, Albers-Schonberg G, Hensens O, Hirshfield J, Hoogsteen K, Liesch J, Springer J: Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent. Proc Natl Acad Sci U S A. 1980 Jul;77(7):3957-61. (PubMed ID 6933445)\" href=\"#reference-A174553\">2</a></sup> More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Moghadasian MH: Clinical pharmacology of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors. Life Sci. 1999;65(13):1329-37. doi: 10.1016/s0024-3205(99)00199-x. (PubMed ID 10503952)\" href=\"#reference-A181421\">12</a></sup> which catalyzes the conversion of HMG-CoA to mevalonic acid and is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as \"bad cholesterol\"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. (PubMed ID 27712954)\" href=\"#reference-A181087\">13</a>,<a class=\"reference-popover-link\" data-content=\"Grundy SM, Stone NJ: 2018 American Heart Association/American College of Cardiology Multisociety Guideline on the Management of Blood Cholesterol: Primary Prevention. JAMA Cardiol. 2019 Apr 10. pii: 2730287. doi: 10.1001/jamacardio.2019.0777. (PubMed ID 30969322)\" href=\"#reference-A181406\">14</a></sup></p><p>Lovastatin and other drugs from the statin class of medications including <a href=\"https://go.drugbank.com/drugs/DB01076\">atorvastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB00175\">pravastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB01098\">rosuvastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB01095\">fluvastatin</a>, and <a href=\"https://go.drugbank.com/drugs/DB00641\">simvastatin</a> are considered first-line options for the treatment of dyslipidemia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. (PubMed ID 27712954)\" href=\"#reference-A181087\">13</a>,<a class=\"reference-popover-link\" data-content=\"Grundy SM, Stone NJ: 2018 American Heart Association/American College of Cardiology Multisociety Guideline on the Management of Blood Cholesterol: Primary Prevention. JAMA Cardiol. 2019 Apr 10. pii: 2730287. doi: 10.1001/jamacardio.2019.0777. (PubMed ID 30969322)\" href=\"#reference-A181406\">14</a></sup> Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kreatsoulas C, Anand SS: The impact of social determinants on cardiovascular disease. Can J Cardiol. 2010 Aug-Sep;26 Suppl C:8C-13C. doi: 10.1016/s0828-282x(10)71075-8. (PubMed ID 20847985)\" href=\"#reference-A181084\">15</a></sup> Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. (PubMed ID 27712954)\" href=\"#reference-A181087\">13</a>,<a class=\"reference-popover-link\" data-content=\"Kannel WB, Castelli WP, Gordon T, McNamara PM: Serum cholesterol, lipoproteins, and the risk of coronary heart disease. The Framingham study. Ann Intern Med. 1971 Jan;74(1):1-12. doi: 10.7326/0003-4819-74-1-1. (PubMed ID 5539274)\" href=\"#reference-A181553\">16</a></sup> Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Authors unspecified: Prevention of cardiovascular events and death with pravastatin in patients with coronary heart disease and a broad range of initial cholesterol levels. N Engl J Med. 1998 Nov 5;339(19):1349-57. doi: 10.1056/NEJM199811053391902. (PubMed ID 9841303)\" href=\"#reference-A181090\">17</a>,<a class=\"reference-popover-link\" data-content=\"Cannon CP, Braunwald E, McCabe CH, Rader DJ, Rouleau JL, Belder R, Joyal SV, Hill KA, Pfeffer MA, Skene AM: Intensive versus moderate lipid lowering with statins after acute coronary syndromes. N Engl J Med. 2004 Apr 8;350(15):1495-504. doi: 10.1056/NEJMoa040583. Epub 2004 Mar 8. (PubMed ID 15007110)\" href=\"#reference-A181093\">18</a>,<a class=\"reference-popover-link\" data-content=\"Ridker PM, Danielson E, Fonseca FA, Genest J, Gotto AM Jr, Kastelein JJ, Koenig W, Libby P, Lorenzatti AJ, MacFadyen JG, Nordestgaard BG, Shepherd J, Willerson JT, Glynn RJ: Rosuvastatin to prevent vascular events in men and women with elevated C-reactive protein. N Engl J Med. 2008 Nov 20;359(21):2195-207. doi: 10.1056/NEJMoa0807646. Epub 2008 Nov 9. (PubMed ID 18997196)\" href=\"#reference-A181096\">19</a>,<a class=\"reference-popover-link\" data-content=\"Nicholls SJ, Ballantyne CM, Barter PJ, Chapman MJ, Erbel RM, Libby P, Raichlen JS, Uno K, Borgman M, Wolski K, Nissen SE: Effect of two intensive statin regimens on progression of coronary disease. N Engl J Med. 2011 Dec 1;365(22):2078-87. doi: 10.1056/NEJMoa1110874. Epub 2011 Nov 15. (PubMed ID 22085316)\" href=\"#reference-A181427\">20</a>,<a class=\"reference-popover-link\" data-content=\"Authors unspecified: MRC/BHF Heart Protection Study of cholesterol lowering with simvastatin in 20,536 high-risk individuals: a randomised placebo-controlled trial. Lancet. 2002 Jul 6;360(9326):7-22. doi: 10.1016/S0140-6736(02)09327-3. (PubMed ID 12114036)\" href=\"#reference-A181475\">21</a>,<a class=\"reference-popover-link\" data-content=\"Authors unspecified: Randomised trial of cholesterol lowering in 4444 patients with coronary heart disease: the Scandinavian Simvastatin Survival Study (4S) Lancet. 1994 Nov 19;344(8934):1383-9. (PubMed ID 7968073)\" href=\"#reference-A181538\">22</a></sup> Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. (PubMed ID 27712954)\" href=\"#reference-A181087\">13</a>,<a class=\"reference-popover-link\" data-content=\"Grundy SM, Stone NJ: 2018 American Heart Association/American College of Cardiology Multisociety Guideline on the Management of Blood Cholesterol: Primary Prevention. JAMA Cardiol. 2019 Apr 10. pii: 2730287. doi: 10.1001/jamacardio.2019.0777. (PubMed ID 30969322)\" href=\"#reference-A181406\">14</a></sup> Evidence has shown that even for low-risk individuals (with &lt;10% risk of a major vascular event occurring within 5 years) statins cause a 20%-22% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Mihaylova B, Emberson J, Blackwell L, Keech A, Simes J, Barnes EH, Voysey M, Gray A, Collins R, Baigent C: The effects of lowering LDL cholesterol with statin therapy in people at low risk of vascular disease: meta-analysis of individual data from 27 randomised trials. Lancet. 2012 Aug 11;380(9841):581-90. doi: 10.1016/S0140-6736(12)60367-5. Epub 2012 May 17. (PubMed ID 22607822)\" href=\"#reference-A181397\">24</a>,<a class=\"reference-popover-link\" data-content=\"Taylor F, Huffman MD, Macedo AF, Moore TH, Burke M, Davey Smith G, Ward K, Ebrahim S: Statins for the primary prevention of cardiovascular disease. Cochrane Database Syst Rev. 2013 Jan 31;(1):CD004816. doi: 10.1002/14651858.CD004816.pub5. (PubMed ID 23440795)\" href=\"#reference-A181403\">23</a></sup></p><p>While all statin medications are considered equally effective from a clinical standpoint, <a href=\"https://go.drugbank.com/drugs/DB01098\">rosuvastatin</a> is considered the most potent; doses of 10 to 40mg <a href=\"https://go.drugbank.com/drugs/DB01098\">rosuvastatin</a> per day were found in clinical studies to result in a 45.8% to 54.6% decrease in LDL cholesterol levels, while lovastatin has been found to have an average decrease in LDL-C of 25-40%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Henwood JM, Heel RC: Lovastatin. A preliminary review of its pharmacodynamic properties and therapeutic use in hyperlipidaemia. Drugs. 1988 Oct;36(4):429-54. doi: 10.2165/00003495-198836040-00003. (PubMed ID 3069436)\" href=\"#reference-A174580\">5</a>,<a class=\"reference-popover-link\" data-content=\"Adams SP, Sekhon SS, Wright JM: Lipid-lowering efficacy of rosuvastatin. Cochrane Database Syst Rev. 2014 Nov 21;(11):CD010254. doi: 10.1002/14651858.CD010254.pub2. (PubMed ID 25415541)\" href=\"#reference-A181409\">25</a>,<a class=\"reference-popover-link\" data-content=\"Pedersen TR, Faergeman O, Kastelein JJ, Olsson AG, Tikkanen MJ, Holme I, Larsen ML, Bendiksen FS, Lindahl C, Szarek M, Tsai J: High-dose atorvastatin vs usual-dose simvastatin for secondary prevention after myocardial infarction: the IDEAL study: a randomized controlled trial. JAMA. 2005 Nov 16;294(19):2437-45. doi: 10.1001/jama.294.19.2437. (PubMed ID 16287954)\" href=\"#reference-A181535\">26</a>,<a class=\"reference-popover-link\" data-content=\"Authors unspecified: Randomised trial of cholesterol lowering in 4444 patients with coronary heart disease: the Scandinavian Simvastatin Survival Study (4S) Lancet. 1994 Nov 19;344(8934):1383-9. (PubMed ID 7968073)\" href=\"#reference-A181538\">22</a>,<a class=\"reference-popover-link\" data-content=\"Jones PH, Davidson MH, Stein EA, Bays HE, McKenney JM, Miller E, Cain VA, Blasetto JW: Comparison of the efficacy and safety of rosuvastatin versus atorvastatin, simvastatin, and pravastatin across doses (STELLAR* Trial). Am J Cardiol. 2003 Jul 15;92(2):152-60. (PubMed ID 12860216)\" href=\"#reference-A1793\">27</a></sup> Potency is thought to correlate to tissue permeability as the more lipophilic statins such as lovastatin are thought to enter endothelial cells by passive diffusion, as opposed to hydrophilic statins such as <a href=\"https://go.drugbank.com/drugs/DB00175\">pravastatin</a> and <a href=\"https://go.drugbank.com/drugs/DB01098\">rosuvastatin</a> which are taken up into hepatocytes through OATP1B1 (organic anion transporter protein 1B1)-mediated transport.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Liao JK, Laufs U: Pleiotropic effects of statins. Annu Rev Pharmacol Toxicol. 2005;45:89-118. doi: 10.1146/annurev.pharmtox.45.120403.095748. (PubMed ID 15822172)\" href=\"#reference-A181424\">31</a>,<a class=\"reference-popover-link\" data-content=\"Elsby R, Hilgendorf C, Fenner K: Understanding the critical disposition pathways of statins to assess drug-drug interaction risk during drug development: it\'s not just about OATP1B1. Clin Pharmacol Ther. 2012 Nov;92(5):584-98. doi: 10.1038/clpt.2012.163. Epub 2012 Oct 10. (PubMed ID 23047648)\" href=\"#reference-A181460\">28</a></sup> Despite these differences in potency, several trials have demonstrated only minimal differences in terms of clinical outcomes between statins.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Authors unspecified: Randomised trial of cholesterol lowering in 4444 patients with coronary heart disease: the Scandinavian Simvastatin Survival Study (4S) Lancet. 1994 Nov 19;344(8934):1383-9. (PubMed ID 7968073)\" href=\"#reference-A181538\">22</a>,<a class=\"reference-popover-link\" data-content=\"Nicholls SJ, Ballantyne CM, Barter PJ, Chapman MJ, Erbel RM, Libby P, Raichlen JS, Uno K, Borgman M, Wolski K, Nissen SE: Effect of two intensive statin regimens on progression of coronary disease. N Engl J Med. 2011 Dec 1;365(22):2078-87. doi: 10.1056/NEJMoa1110874. Epub 2011 Nov 15. (PubMed ID 22085316)\" href=\"#reference-A181427\">20</a></sup></p>','C24H36O5','DB00227','Approved, Investigational','Small Molecule','Average: 404.5396 Monoisotopic: 404.256274262 ',' , C10AA — HMG CoA reductase inhibitors , C10A — LIPID MODIFYING AGENTS, PLAIN , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , C10BA — HMG CoA reductase inhibitors in combination with other lipid modifying agents , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM','<p>Lovastatin Cmax was found to be 3.013ng/mL with a Tmax of 3.36 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p><p>Plasma concentrations of total radioactivity (lovastatin plus 14C-metabolites) peaked at 2 hours and declined rapidly to about 10% of peak by 24 hours postdose. Absorption of lovastatin, estimated relative to an intravenous reference dose, in each of four animal species tested, averaged about 30% of an oral dose. In animal studies, after oral dosing, lovastatin had high selectivity for the liver, where it achieved substantially higher concentrations than in non-target tissues. Lovastatin undergoes extensive first-pass extraction in the liver, its primary site of action, with subsequent excretion of drug equivalents in the bile. As a consequence of extensive hepatic extraction of lovastatin, the availability of drug to the general circulation is low and variable. In a single dose study in four hypercholesterolemic patients, it was estimated that less than 5% of an oral dose of lovastatin reaches the general circulation as active inhibitors. Following administration of lovastatin tablets the coefficient of variation, based on between-subject variability, was approximately 40% for the area under the curve (AUC) of total inhibitory activity in the general circulation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a>,<a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p><p>The peak concentrations of lovastatin when a dose of 10-40 mg is administered are reported to range from 1.04-4.03 ng/ml and an AUC of 14-53 ng.h/ml. This indicates that lovastatin presents a dose-dependent pharmacokinetic profile.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lamson M, Phillips G, Shen J, Lukacsko P, Friedhoff L, Niecestro RM: Pharmacokinetics of lovastatin extended-release dosage form (Lovastatin XL) in healthy volunteers. Biopharm Drug Dispos. 2002 May;23(4):143-9. doi: 10.1002/bdd.304. (PubMed ID 12015788)\" href=\"#reference-A174586\">8</a></sup> When lovastatin was given under fasting conditions, plasma concentrations of both active and total inhibitors were on average about two-thirds those found when lovastatin was administered immediately after a standard test meal.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p><p>Genetic differences in the OATP1B1 (Organic-Anion-Transporting Polypeptide 1B1) hepatic transporter encoded by the SCLCO1B1 gene (Solute Carrier Organic Anion Transporter family member 1B1) have been shown to impact lovastatin pharmacokinetics.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Zhao G, Liu M, Wu X, Li G, Qiu F, Gu J, Zhao L: Effect of polymorphisms in CYP3A4, PPARA, NR1I2, NFKB1, ABCG2 and SLCO1B1 on the pharmacokinetics of lovastatin in healthy Chinese volunteers. Pharmacogenomics. 2017 Jan;18(1):65-75. doi: 10.2217/pgs.16.31. Epub 2016 Dec 14. (PubMed ID 27967318)\" href=\"#reference-A181943\">34</a></sup> Evidence from pharmacogenetic studies of the c.521T&gt;C single nucleotide polymorphism (SNP) showed that lovastatin Cmax and AUC were 340 and 286% higher, respectively, for individuals homozygous for 521CC compared to homozygous 521TT individuals.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tornio A, Vakkilainen J, Neuvonen M, Backman JT, Neuvonen PJ, Niemi M: SLCO1B1 polymorphism markedly affects the pharmacokinetics of lovastatin acid. Pharmacogenet Genomics. 2015 Aug;25(8):382-7. doi: 10.1097/FPC.0000000000000148. (PubMed ID 26020121)\" href=\"#reference-A181946\">35</a></sup> The 521CC genotype is also associated with a marked increase in the risk of developing myopathy, likely secondary to increased systemic exposure.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Xiang Q, Chen SQ, Ma LY, Hu K, Zhang Z, Mu GY, Xie QF, Zhang XD, Cui YM: Association between SLCO1B1 T521C polymorphism and risk of statin-induced myopathy: a meta-analysis. Pharmacogenomics J. 2018 Dec;18(6):721-729. doi: 10.1038/s41397-018-0054-0. Epub 2018 Sep 24. (PubMed ID 30250148)\" href=\"#reference-A181955\">36</a></sup> Other statin drugs impacted by this polymorphism include <a href=\"https://go.drugbank.com/drugs/DB01098\">rosuvastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB08860\">pitavastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB01076\">atorvastatin</a>, <a href=\"https://go.drugbank.com/drugs/DB00641\">simvastatin</a>, and <a href=\"https://go.drugbank.com/drugs/DB00175\">pravastatin</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Elsby R, Hilgendorf C, Fenner K: Understanding the critical disposition pathways of statins to assess drug-drug interaction risk during drug development: it\'s not just about OATP1B1. Clin Pharmacol Ther. 2012 Nov;92(5):584-98. doi: 10.1038/clpt.2012.163. Epub 2012 Oct 10. (PubMed ID 23047648)\" href=\"#reference-A181460\">28</a></sup></p><p>While specific dosage instructions are not included in the available product monographs for lovastatin, individuals with the above-mentioned c.521CC OATP1B1 genotype should be monitored for development of adverse effects from increased exposure to the drug, such as muscle pain and risk of rhabdomyolysis, particularly at higher doses.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic ester derivatives of a fatty acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000324\" rel=\"noopener\" target=\"_blank\">Fatty acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Not Available','Not Available','34168','75330-75-5','40303','CHEMBL503','48085','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organic compounds containing an oxan-2- one moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001244\" rel=\"noopener\" target=\"_blank\">Delta valerolactones</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organic compounds containing an oxan-2- one moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001244\" rel=\"noopener\" target=\"_blank\">Delta valerolactones</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic ester derivatives of a fatty acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000324\" rel=\"noopener\" target=\"_blank\">Fatty acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta valerolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta_valerolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acyl</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">polyketide, fatty acid ester, delta-lactone, carbobicyclic compound, statin (naturally occurring) (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:40303\" rel=\"noopener\" target=\"_blank\">CHEBI:40303</a>) </span></span></dd></dl>','Lactones','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.','Delta valerolactones','<li>Avoid grapefruit products. Grapefruit products may increase the risk for lovastatin related adverse effects such as myopathy and rhabdomyolysis.</li>\n<li>Take with food. Food increases bioavailability.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , Anticholesteremic Agents , BSEP/ABCB11 Substrates , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (weak) , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (moderate) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Hydroxymethylglutaryl-CoA Reductase Inhibitors , Hypolipidemic Agents , Hypolipidemic Agents Indicated for Hyperlipidemia , Lipid Modifying Agents , Lipid Regulating Agents , OATP1B1/SLCO1B1 Inhibitors , OATP1B1/SLCO1B1 Substrates , P-glycoprotein inhibitors , Photosensitizing Agents , UGT1A1 Substrates , UGT1A3 substrates , UGT2B7 substrates','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>174.5 °C</td><td>\'MSDS\'</td></tr><tr><td>boiling point (°C)</td><td>559.2 ºC at 760 mmHg</td><td>Chemspider</td></tr><tr><td>water solubility</td><td>0.0004 mg/mL</td><td>\'MSDS\'</td></tr><tr><td>logP</td><td>4.08</td><td>\'MSDS\'</td></tr><tr><td>pKa</td><td>13.49</td><td>Chuong M. et al. (2013). International Journal of Applied Pharmaceutics.</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">polyketide, fatty acid ester, delta-lactone, carbobicyclic compound, statin (naturally occurring) (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:40303\" rel=\"noopener\" target=\"_blank\">CHEBI:40303</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014372\" rel=\"noopener\" target=\"_blank\">HMDB0014372</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00359\" rel=\"noopener\" target=\"_blank\">D00359</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07074\" rel=\"noopener\" target=\"_blank\">C07074</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=53232\" rel=\"noopener\" target=\"_blank\">53232</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508223\" rel=\"noopener\" target=\"_blank\">46508223</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.48085.html\" rel=\"noopener\" target=\"_blank\">48085</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=34168\" rel=\"noopener\" target=\"_blank\">34168</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=6472\" rel=\"noopener\" target=\"_blank\">6472</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=40303\" rel=\"noopener\" target=\"_blank\">40303</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL503\" rel=\"noopener\" target=\"_blank\">CHEMBL503</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003812841\" rel=\"noopener\" target=\"_blank\">ZINC000003812841</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000551\" rel=\"noopener\" target=\"_blank\">DAP000551</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450272\" rel=\"noopener\" target=\"_blank\">PA450272</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2739\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/803\" rel=\"noopener\" target=\"_blank\">803</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic3/altocor.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/lovastatin.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Lovastatin\" rel=\"noopener\" target=\"_blank\">Lovastatin</a></dd></dl>','<li>Avoid grapefruit products. Grapefruit products may increase the risk for lovastatin related adverse effects such as myopathy and rhabdomyolysis.</li>\n<li>Take with food. Food increases bioavailability.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A174550\">Boruta T, Bizukojc M: Production of lovastatin and itaconic acid by Aspergillus terreus: a comparative perspective. World J Microbiol Biotechnol. 2017 Feb;33(2):34. doi: 10.1007/s11274-017-2206-9. Epub 2017 Jan 19. [<a href=\"/articles/A174550\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174553\">Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffman C, Rothrock J, Lopez M, Joshua H, Harris E, Patchett A, Monaghan R, Currie S, Stapley E, Albers-Schonberg G, Hensens O, Hirshfield J, Hoogsteen K, Liesch J, Springer J: Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent. Proc Natl Acad Sci U S A. 1980 Jul;77(7):3957-61. [<a href=\"/articles/A174553\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174565\">Endo A: The origin of the statins. 2004. Atheroscler Suppl. 2004 Oct;5(3):125-30. doi: 10.1016/j.atherosclerosissup.2004.08.033. [<a href=\"/articles/A174565\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174568\">Chiloeches A, Lasa M, Brihuega F, Montes A, Toro MJ: Effects of lovastatin on adenylyl cyclase activity and G proteins in GH4C1 cells. FEBS Lett. 1995 Mar 13;361(1):46-50. [<a href=\"/articles/A174568\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174580\">Henwood JM, Heel RC: Lovastatin. A preliminary review of its pharmacodynamic properties and therapeutic use in hyperlipidaemia. Drugs. 1988 Oct;36(4):429-54. doi: 10.2165/00003495-198836040-00003. [<a href=\"/articles/A174580\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174583\">Lennernas H, Fager G: Pharmacodynamics and pharmacokinetics of the HMG-CoA reductase inhibitors. Similarities and differences. Clin Pharmacokinet. 1997 May;32(5):403-25. doi: 10.2165/00003088-199732050-00005. [<a href=\"/articles/A174583\" target=\"_blank\">Article</a>] </li><li id=\"reference-A414\">Whirl-Carrillo M, McDonagh EM, Hebert JM, Gong L, Sangkuhl K, Thorn CF, Altman RB, Klein TE: Pharmacogenomics knowledge for personalized medicine. Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96. [<a href=\"/articles/A414\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174586\">Lamson M, Phillips G, Shen J, Lukacsko P, Friedhoff L, Niecestro RM: Pharmacokinetics of lovastatin extended-release dosage form (Lovastatin XL) in healthy volunteers. Biopharm Drug Dispos. 2002 May;23(4):143-9. doi: 10.1002/bdd.304. [<a href=\"/articles/A174586\" target=\"_blank\">Article</a>] </li><li id=\"reference-A35026\">Neuvonen PJ, Backman JT, Niemi M: Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin. Clin Pharmacokinet. 2008;47(7):463-74. doi: 10.2165/00003088-200847070-00003. [<a href=\"/articles/A35026\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174589\">Greenspan MD, Yudkovitz JB, Alberts AW, Argenbright LS, Arison BH, Smith JL: Metabolism of lovastatin by rat and human liver microsomes in vitro. Drug Metab Dispos. 1988 Sep-Oct;16(5):678-82. [<a href=\"/articles/A174589\" target=\"_blank\">Article</a>] </li><li id=\"reference-A15320\">Draganov DI, Stetson PL, Watson CE, Billecke SS, La Du BN: Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation. J Biol Chem. 2000 Oct 27;275(43):33435-42. [<a href=\"/articles/A15320\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181421\">Moghadasian MH: Clinical pharmacology of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors. Life Sci. 1999;65(13):1329-37. doi: 10.1016/s0024-3205(99)00199-x. [<a href=\"/articles/A181421\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181087\">Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. [<a href=\"/articles/A181087\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181406\">Grundy SM, Stone NJ: 2018 American Heart Association/American College of Cardiology Multisociety Guideline on the Management of Blood Cholesterol: Primary Prevention. JAMA Cardiol. 2019 Apr 10. pii: 2730287. doi: 10.1001/jamacardio.2019.0777. [<a href=\"/articles/A181406\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181084\">Kreatsoulas C, Anand SS: The impact of social determinants on cardiovascular disease. Can J Cardiol. 2010 Aug-Sep;26 Suppl C:8C-13C. doi: 10.1016/s0828-282x(10)71075-8. [<a href=\"/articles/A181084\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181553\">Kannel WB, Castelli WP, Gordon T, McNamara PM: Serum cholesterol, lipoproteins, and the risk of coronary heart disease. The Framingham study. Ann Intern Med. 1971 Jan;74(1):1-12. doi: 10.7326/0003-4819-74-1-1. [<a href=\"/articles/A181553\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181090\">Authors unspecified: Prevention of cardiovascular events and death with pravastatin in patients with coronary heart disease and a broad range of initial cholesterol levels. N Engl J Med. 1998 Nov 5;339(19):1349-57. doi: 10.1056/NEJM199811053391902. [<a href=\"/articles/A181090\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181093\">Cannon CP, Braunwald E, McCabe CH, Rader DJ, Rouleau JL, Belder R, Joyal SV, Hill KA, Pfeffer MA, Skene AM: Intensive versus moderate lipid lowering with statins after acute coronary syndromes. N Engl J Med. 2004 Apr 8;350(15):1495-504. doi: 10.1056/NEJMoa040583. Epub 2004 Mar 8. [<a href=\"/articles/A181093\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181096\">Ridker PM, Danielson E, Fonseca FA, Genest J, Gotto AM Jr, Kastelein JJ, Koenig W, Libby P, Lorenzatti AJ, MacFadyen JG, Nordestgaard BG, Shepherd J, Willerson JT, Glynn RJ: Rosuvastatin to prevent vascular events in men and women with elevated C-reactive protein. N Engl J Med. 2008 Nov 20;359(21):2195-207. doi: 10.1056/NEJMoa0807646. Epub 2008 Nov 9. [<a href=\"/articles/A181096\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181427\">Nicholls SJ, Ballantyne CM, Barter PJ, Chapman MJ, Erbel RM, Libby P, Raichlen JS, Uno K, Borgman M, Wolski K, Nissen SE: Effect of two intensive statin regimens on progression of coronary disease. N Engl J Med. 2011 Dec 1;365(22):2078-87. doi: 10.1056/NEJMoa1110874. Epub 2011 Nov 15. [<a href=\"/articles/A181427\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181475\">Authors unspecified: MRC/BHF Heart Protection Study of cholesterol lowering with simvastatin in 20,536 high-risk individuals: a randomised placebo-controlled trial. Lancet. 2002 Jul 6;360(9326):7-22. doi: 10.1016/S0140-6736(02)09327-3. [<a href=\"/articles/A181475\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181538\">Authors unspecified: Randomised trial of cholesterol lowering in 4444 patients with coronary heart disease: the Scandinavian Simvastatin Survival Study (4S) Lancet. 1994 Nov 19;344(8934):1383-9. [<a href=\"/articles/A181538\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181403\">Taylor F, Huffman MD, Macedo AF, Moore TH, Burke M, Davey Smith G, Ward K, Ebrahim S: Statins for the primary prevention of cardiovascular disease. Cochrane Database Syst Rev. 2013 Jan 31;(1):CD004816. doi: 10.1002/14651858.CD004816.pub5. [<a href=\"/articles/A181403\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181397\">Mihaylova B, Emberson J, Blackwell L, Keech A, Simes J, Barnes EH, Voysey M, Gray A, Collins R, Baigent C: The effects of lowering LDL cholesterol with statin therapy in people at low risk of vascular disease: meta-analysis of individual data from 27 randomised trials. Lancet. 2012 Aug 11;380(9841):581-90. doi: 10.1016/S0140-6736(12)60367-5. Epub 2012 May 17. [<a href=\"/articles/A181397\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181409\">Adams SP, Sekhon SS, Wright JM: Lipid-lowering efficacy of rosuvastatin. Cochrane Database Syst Rev. 2014 Nov 21;(11):CD010254. doi: 10.1002/14651858.CD010254.pub2. [<a href=\"/articles/A181409\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181535\">Pedersen TR, Faergeman O, Kastelein JJ, Olsson AG, Tikkanen MJ, Holme I, Larsen ML, Bendiksen FS, Lindahl C, Szarek M, Tsai J: High-dose atorvastatin vs usual-dose simvastatin for secondary prevention after myocardial infarction: the IDEAL study: a randomized controlled trial. JAMA. 2005 Nov 16;294(19):2437-45. doi: 10.1001/jama.294.19.2437. [<a href=\"/articles/A181535\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1793\">Jones PH, Davidson MH, Stein EA, Bays HE, McKenney JM, Miller E, Cain VA, Blasetto JW: Comparison of the efficacy and safety of rosuvastatin versus atorvastatin, simvastatin, and pravastatin across doses (STELLAR* Trial). Am J Cardiol. 2003 Jul 15;92(2):152-60. [<a href=\"/articles/A1793\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181460\">Elsby R, Hilgendorf C, Fenner K: Understanding the critical disposition pathways of statins to assess drug-drug interaction risk during drug development: it\'s not just about OATP1B1. Clin Pharmacol Ther. 2012 Nov;92(5):584-98. doi: 10.1038/clpt.2012.163. Epub 2012 Oct 10. [<a href=\"/articles/A181460\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31225\">Jacobsen W, Kirchner G, Hallensleben K, Mancinelli L, Deters M, Hackbarth I, Benet LZ, Sewing KF, Christians U: Comparison of cytochrome P-450-dependent metabolism and drug interactions of the 3-hydroxy-3-methylglutaryl-CoA reductase inhibitors lovastatin and pravastatin in the liver. Drug Metab Dispos. 1999 Feb;27(2):173-9. [<a href=\"/articles/A31225\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181925\">Bradford RH, Shear CL, Chremos AN, Dujovne CA, Franklin FA, Grillo RB, Higgins J, Langendorfer A, Nash DT, Pool JL, et al.: Expanded Clinical Evaluation of Lovastatin (EXCEL) study results: two-year efficacy and safety follow-up. Am J Cardiol. 1994 Oct 1;74(7):667-73. doi: 10.1016/0002-9149(94)90307-7. [<a href=\"/articles/A181925\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181424\">Liao JK, Laufs U: Pleiotropic effects of statins. Annu Rev Pharmacol Toxicol. 2005;45:89-118. doi: 10.1146/annurev.pharmtox.45.120403.095748. [<a href=\"/articles/A181424\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181559\">Weitz-Schmidt G, Welzenbach K, Brinkmann V, Kamata T, Kallen J, Bruns C, Cottens S, Takada Y, Hommel U: Statins selectively inhibit leukocyte function antigen-1 by binding to a novel regulatory integrin site. Nat Med. 2001 Jun;7(6):687-92. doi: 10.1038/89058. [<a href=\"/articles/A181559\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181937\">Mahmoud AM, Aboul-Soud MA, Han J, Al-Sheikh YA, Al-Abd AM, El-Shemy HA: Transcriptional profiling of breast cancer cells in response to mevinolin: Evidence of cell cycle arrest, DNA degradation and apoptosis. Int J Oncol. 2016 May;48(5):1886-94. doi: 10.3892/ijo.2016.3418. Epub 2016 Mar 4. [<a href=\"/articles/A181937\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181943\">Zhao G, Liu M, Wu X, Li G, Qiu F, Gu J, Zhao L: Effect of polymorphisms in CYP3A4, PPARA, NR1I2, NFKB1, ABCG2 and SLCO1B1 on the pharmacokinetics of lovastatin in healthy Chinese volunteers. Pharmacogenomics. 2017 Jan;18(1):65-75. doi: 10.2217/pgs.16.31. Epub 2016 Dec 14. [<a href=\"/articles/A181943\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181946\">Tornio A, Vakkilainen J, Neuvonen M, Backman JT, Neuvonen PJ, Niemi M: SLCO1B1 polymorphism markedly affects the pharmacokinetics of lovastatin acid. Pharmacogenet Genomics. 2015 Aug;25(8):382-7. doi: 10.1097/FPC.0000000000000148. [<a href=\"/articles/A181946\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181955\">Xiang Q, Chen SQ, Ma LY, Hu K, Zhang Z, Mu GY, Xie QF, Zhang XD, Cui YM: Association between SLCO1B1 T521C polymorphism and risk of statin-induced myopathy: a meta-analysis. Pharmacogenomics J. 2018 Dec;18(6):721-729. doi: 10.1038/s41397-018-0054-0. Epub 2018 Sep 24. [<a href=\"/articles/A181955\" target=\"_blank\">Article</a>] </li><li id=\"reference-A15235\">Lin YC, Lin JH, Chou CW, Chang YF, Yeh SH, Chen CC: Statins increase p21 through inhibition of histone deacetylase activity and release of promoter-associated HDAC1/2. Cancer Res. 2008 Apr 1;68(7):2375-83. doi: 10.1158/0008-5472.CAN-07-5807. [<a href=\"/articles/A15235\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182258\">Harper CR, Jacobson TA: The broad spectrum of statin myopathy: from myalgia to rhabdomyolysis. Curr Opin Lipidol. 2007 Aug;18(4):401-8. doi: 10.1097/MOL.0b013e32825a6773. [<a href=\"/articles/A182258\" target=\"_blank\">Article</a>] </li><li id=\"reference-T412\">Acton A. (2013). Advances in Lovastatin Research and Application. ScholarlyBrief. </li><li id=\"reference-T415\">Loughlin K. and Generali J. (2006). Prescription Drugs: Alternative Uses, Alternative Cures. Free Press. [<a href=\"https://www.google.com/search?tbo=p&amp;tbm=bks&amp;q=0-7432-9925-6\" rel=\"noopener\" target=\"_blank\">ISBN:0-7432-9925-6</a>] </li><li id=\"reference-L12561\">FDA Approved Drug Products: Altoprev (lovastatin extended-release) oral tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021316s036lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L12564\">FDA Approved Drug Products: Mevacor (lovastatin) oral tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019643s088lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-F4661\">FDA Label - Lovastatin [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/661/original/FDA_Label_-_Lovastatin.pdf?1564095428\" target=\"_blank\">File</a>] </li><li id=\"reference-F4664\">Health Canada Monograph - Lovastatin [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/664/original/Health_Canada_Monograph_-_Lovastatin.PDF?1564095447\" target=\"_blank\">File</a>] </li></ol>','<p>Lovastatin half-life is reported to be of 13.37 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup> The elimination half-life of the hydroxy acid form of lovastatin is reported to be of 0.7-3 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lennernas H, Fager G: Pharmacodynamics and pharmacokinetics of the HMG-CoA reductase inhibitors. Similarities and differences. Clin Pharmacokinet. 1997 May;32(5):403-25. doi: 10.2165/00003088-199732050-00005. (PubMed ID 9160173)\" href=\"#reference-A174583\">6</a></sup></p>','HMDB0014372','(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate','InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1','PCZOHLXUXFIOCF-BXMDZJJMSA-N','<p>Lovastatin is indicated to reduce the risk of myocardial infarction, unstable angina, and the need for coronary revascularization procedures in individuals without symptomatic cardiovascular disease, average to moderately elevated total-C and LDL-C, and below average HDL-C. It is indicated as an intervention alternative in individuals presenting dyslipidemia at risk of developing atherosclerotic vascular disease. The administration of this agent should be accompanied by the implementation of a fat and cholesterol-restricted diet.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a></sup></p><p>Therapy with lipid-altering agents should be a component of multiple risk factor intervention in those individuals at significantly increased risk for atherosclerotic vascular disease due to hypercholesterolemia. Lovastatin is indicated as an adjunct to diet for the reduction of elevated total-C and LDL-C levels in patients with primary hypercholesterolemia (Types IIa and IIb2), when the response to diet restricted in saturated fat and cholesterol and to other nonpharmacological measures alone has been inadequate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a>,<a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p><p>Lovastatin is also indicated to slow the progression of coronary atherosclerosis in patients with coronary heart disease as part of a treatment strategy to lower total-C and LDL-C to target levels.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a></sup></p><p>Lovastatin is indicated as an adjunct to diet to reduce total-C, LDL-C and apolipoprotein B levels in adolescent boys and girls with Heterozygous Familial Hypercholesterolemia (HeFH) who are at least one year post-menarche, 10 to 17 years of age, with HeFH if after an adequate trial of diet therapy the following findings are present: LDL-C remains greater than 189 mg/dL or LDL-C remains greater than 160 mg/dL and there is a positive family history of premature cardiovascular disease or two or more other CVD risk factors are present in the adolescent patient.</p><p>Before administering lovastatin, it is important to rule out the presence of secondary causes of hypercholesterolemia and a lipid profile should be performed.</p><p>Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD. Statin-indicated conditions include diabetes mellitus, clinical atherosclerosis (including myocardial infarction, acute coronary syndromes, stable angina, documented coronary artery disease, stroke, trans ischemic attack (TIA), documented carotid disease, peripheral artery disease, and claudication), abdominal aortic aneurysm, chronic kidney disease, and severely elevated LDL-C levels.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Anderson TJ, Gregoire J, Pearson GJ, Barry AR, Couture P, Dawes M, Francis GA, Genest J Jr, Grover S, Gupta M, Hegele RA, Lau DC, Leiter LA, Lonn E, Mancini GB, McPherson R, Ngui D, Poirier P, Sievenpiper JL, Stone JA, Thanassoulis G, Ward R: 2016 Canadian Cardiovascular Society Guidelines for the Management of Dyslipidemia for the Prevention of Cardiovascular Disease in the Adult. Can J Cardiol. 2016 Nov;32(11):1263-1282. doi: 10.1016/j.cjca.2016.07.510. Epub 2016 Jul 25. (PubMed ID 27712954)\" href=\"#reference-A181087\">13</a>,<a class=\"reference-popover-link\" data-content=\"Grundy SM, Stone NJ: 2018 American Heart Association/American College of Cardiology Multisociety Guideline on the Management of Blood Cholesterol: Primary Prevention. JAMA Cardiol. 2019 Apr 10. pii: 2730287. doi: 10.1001/jamacardio.2019.0777. (PubMed ID 30969322)\" href=\"#reference-A181406\">14</a></sup></p>','C07074','D00359','Organic compounds','<p>Lovastatin is given as a lactone prodrug and thus, in order to produce its mechanism of action, it is required to be converted to the active beta-hydroxy form. This drug activation process does not seem to be related to CYP isoenzyme activity<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Whirl-Carrillo M, McDonagh EM, Hebert JM, Gong L, Sangkuhl K, Thorn CF, Altman RB, Klein TE: Pharmacogenomics knowledge for personalized medicine. Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96. (PubMed ID 22992668)\" href=\"#reference-A414\">7</a></sup> but rather to be controlled by the activity of serum paraoxonase.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Draganov DI, Stetson PL, Watson CE, Billecke SS, La Du BN: Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation. J Biol Chem. 2000 Oct 27;275(43):33435-42. (PubMed ID 10931838)\" href=\"#reference-A15320\">11</a></sup></p><p>Lovastatin is metabolized by the microsomal hepatic enzyme system (Cytochrome P-450 isoform 3A4). The major active metabolites present in human plasma are the β-hydroxy acid of lovastatin, its 6\'-hydroxy, 6\'-hydroxymethyl, and 6\'-exomethylene derivatives.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup> The uptake of lovastatin by the liver is enhanced by the activity of OATP1B1.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Neuvonen PJ, Backman JT, Niemi M: Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin. Clin Pharmacokinet. 2008;47(7):463-74. doi: 10.2165/00003088-200847070-00003. (PubMed ID 18563955)\" href=\"#reference-A35026\">9</a></sup> </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteropolycyclic compounds','803','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000099?highlight[compounds][]=DB00227&amp;highlight[proteins][]=DB00227\">Lovastatin Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450272','<p>Both lovastatin and its β-hydroxy acid metabolite are highly bound (&gt;95%) to human plasma proteins, largely due to its lipophilicity. Animal studies demonstrated that lovastatin crosses the blood-brain and placental barriers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a>,<a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p>','53232','46508223','<p>Following an oral dose of 14C-labeled lovastatin to man, 10% of the dose was excreted in urine and 83% in feces. The latter represents absorbed drug excreted in bile, together with unabsorbed drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p>','RxList Drug Page','6472','[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC','Solid','Delta valerolactones','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta valerolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta_valerolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acyl</span></span></span>','Organoheterocyclic compounds','<span class=\"citations\"><p>Donald F. Gerson, Xinfa Xiao, \"Process for the production of lovastatin using Coniothyrium fuckelii.\" U.S. Patent US5409820, issued January, 1984.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5409820&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5409820</a>','DAP000551','<p>The median lethal dose of lovastatin is higher than 15 g/m2. Five healthy human volunteers have received up to 200 mg of lovastatin as a single dose without clinically significant adverse experiences. A few cases of accidental overdosage have been reported; no patients had any specific symptoms, and all patients recovered without sequelae. The maximum dose taken was 5 to 6 g.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a></sup></p><p>In carcinogenic studies, there is an increase in the incidence of hepatocellular carcinomas and adenomas, pulmonary adenomas, papilloma in non-glandular mucose in stomach and thyroid neoplasms. However, with respect to effects on fertility, lovastatin has been reported to present testicular atrophy, decreased spermatogenesis, spermatocytic degeneration and giant cell formation which derived into decreased fertility in males. Lastly, there is no evidence of mutagenicity induced by lovastatin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - Lovastatin\" href=\"#reference-F4661\">43</a></sup></p>','9LHU78OQFD','<p>Lovastatin is able to cross the blood-brain barrier and placenta.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Health Canada Monograph - Lovastatin\" href=\"#reference-F4664\">44</a></sup></p>','Lovastatin','ZINC000003812841'),(20,'Nevirapine','nevirapine','Nevirapine is a non-nucleoside reverse transcriptase inhibitor used as part of a management regimen for HIV-1 virus infection.','Viramune','Nevirapine','<p>A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. Structurally, nevirapine belongs to the dipyridodiazepinone chemical class.</p>','C15H14N4O','DB00238','Approved','Small Molecule','Average: 266.2979 Monoisotopic: 266.11676109 ',' , J05AG — Non-nucleoside reverse transcriptase inhibitors , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE','<p>Nevirapine is readily absorbed (greater than 90%) after oral administration in healthy subjects and adults with HIV-1 infection. The absolute bioavailability in healthy adults following a single dose administration is 93 ± 9% (mean ± SD) for a 50 mg tablet and 91 ± 8% for an oral solution. Peak plasma nevirapine concentrations of 2 ± 0.4 mcg/mL (7.5 micromolar) were attained by 4 hours following a single 200 mg dose. Nevirapine tablets and suspension have been shown to be comparably bioavailable and interchangeable at doses up to 200 mg. When the oral tablet is given with a high-fat meal, the extent of absorption is compared to that of the fasted-state. </p>','','Human Immunodeficiency Virus','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a pyridine fused to a diazepine ring. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002782\" rel=\"noopener\" target=\"_blank\">Pyridodiazepines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004152\" rel=\"noopener\" target=\"_blank\">Methylpyridines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001336\" rel=\"noopener\" target=\"_blank\">1,4-diazepines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 3 more</a>','Not Available','Not Available','1434','129618-40-2','63613','CHEMBL57','4308','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004707\" rel=\"noopener\" target=\"_blank\">Organic nitrogen compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds formally derived from ammonia by replacing one, two or three hydrogen atoms by hydrocarbyl groups, and having the general structures RNH2 (primary amines), R2NH (secondary amines), R3N (tertiary amines).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002449\" rel=\"noopener\" target=\"_blank\">Amines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003902\" rel=\"noopener\" target=\"_blank\">Alkyldiarylamines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a pyridine fused to a diazepine ring. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002782\" rel=\"noopener\" target=\"_blank\">Pyridodiazepines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004152\" rel=\"noopener\" target=\"_blank\">Methylpyridines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001336\" rel=\"noopener\" target=\"_blank\">1,4-diazepines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 3 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyldiarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methylpyridine</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Para-diazepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrido-para-diazepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dipyridodiazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63613\" rel=\"noopener\" target=\"_blank\">CHEBI:63613</a>) </span></span></dd></dl>','Organonitrogen compounds','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.','Alkyldiarylamines','<li>Avoid alcohol.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Anti-HIV Agents , Anti-Infective Agents , Anti-Retroviral Agents , Antiinfectives for Systemic Use , Antiviral Agents , Antivirals for Systemic Use , Antivirals used in combination for the treatment of HIV infections , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (weak) , Cytochrome P-450 CYP2A6 Substrates , Cytochrome P-450 CYP2B6 Inducers , Cytochrome P-450 CYP2B6 Inducers (strong) , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2C9 Inducers , Cytochrome P-450 CYP2C9 Inducers (strength unknown) , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (weak) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (weak) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Direct Acting Antivirals , Enzyme Inhibitors , Hepatotoxic Agents , Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor , Inducers of Drug Clearance , Non-Nucleoside Reverse Transcriptase Inhibitors , Nonnucleoside Reverse Transcriptase Inhibitors , Nucleic Acid Synthesis Inhibitors , OCT1 inhibitors , Pyridines , Reverse Transcriptase Inhibitors','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>196.06</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>0.7046 mg/L</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>2.5</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>Caco2 permeability</td><td>-4.52</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dipyridodiazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63613\" rel=\"noopener\" target=\"_blank\">CHEBI:63613</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014383\" rel=\"noopener\" target=\"_blank\">HMDB0014383</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00435\" rel=\"noopener\" target=\"_blank\">D00435</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07263\" rel=\"noopener\" target=\"_blank\">C07263</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4463\" rel=\"noopener\" target=\"_blank\">4463</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506789\" rel=\"noopener\" target=\"_blank\">46506789</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.4308.html\" rel=\"noopener\" target=\"_blank\">4308</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=1434\" rel=\"noopener\" target=\"_blank\">1434</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=53654\" rel=\"noopener\" target=\"_blank\">53654</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=63613\" rel=\"noopener\" target=\"_blank\">63613</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL57\" rel=\"noopener\" target=\"_blank\">CHEMBL57</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000000004778\" rel=\"noopener\" target=\"_blank\">ZINC000000004778</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000184\" rel=\"noopener\" target=\"_blank\">DAP000184</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450616\" rel=\"noopener\" target=\"_blank\">PA450616</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/NVP\" rel=\"noopener\" target=\"_blank\">NVP</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic2/nevira.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/nevirapine.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Nevirapine\" rel=\"noopener\" target=\"_blank\">Nevirapine</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','<span class=\"not-available\">Not Available</span>','<p>45 hours</p>','HMDB0014383','2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one','InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)','NQDJXKOVJZTUJA-UHFFFAOYSA-N','<p>For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.</p>','C07263','D00435','Organic compounds','<p>Hepatic. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','NVP','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000642?highlight[compounds][]=DB00238&amp;highlight[proteins][]=DB00238\">Nevirapine Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000743?highlight[compounds][]=DB00238&amp;highlight[proteins][]=DB00238\">Nevirapine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450616','<p>60% bound to plasma protein. </p>','4463','46506789','<p>Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (&lt;5%) of the radioactivity in urine (representing &lt;3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.</p>','RxList Drug Page','53654','CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1','Solid','Amines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyldiarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methylpyridine</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Para-diazepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrido-para-diazepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 10 more</a>','Organic nitrogen compounds','<a href=\"https://www.google.com/?tbm=pts#q=5366972&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5366972</a>','DAP000184','<p>Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease. The most common adverse reaction is rash. </p>','99DK7FVK1H','','Nevirapine','ZINC000000004778'),(21,'Doxycycline','doxycycline','Doxycycline is a tetracycline antibiotic used to treat a wide variety of bacterial infections.','Acticlate, Adoxa, Apprilon, Atridox, Doryx, Doxy, Doxycin, Lymepak, Mondoxyne, Monodox, Morgidox, Okebo, Oracea, Periostat, Targadox, Vibramycin','Doxycycline','<p>Doxycycline is a broad-spectrum antibiotic synthetically derived from oxytetracycline <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. This drug is a second-generation tetracycline, exhibiting lesser toxicity than first-generation tetracyclines <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Smilack JD: The tetracyclines. Mayo Clin Proc. 1999 Jul;74(7):727-9. doi: 10.4065/74.7.727. (PubMed ID 10405705)\" href=\"#reference-A174034\">7</a></sup>. Doxycycline may be used to treat a wide range of bacterial infections, depending on the results of antibiotic susceptibility testing.</p>','C22H24N2O8','DB00254','Approved, Investigational, Vet approved','Small Molecule','Average: 444.4346 Monoisotopic: 444.153265754 ',' , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , A01AB — Antiinfectives and antiseptics for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE','<p>Tetracyclines, such as doxycycline, are readily absorbed and are bound to plasma proteins by varying degrees. Doxycycline is almost completely absorbed after oral administration. This drug is highly lipid soluble and has a low affinity for calcium binding <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Absorption is not significantly affected by the concomitant ingestion of food or milk <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>. Peak serum levels of approximately 2.6 mcg/ml are reached at 2 hours following a 200 mg tablet oral dose <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a>','Not Available','Not Available','50041429','564-25-0','50845','CHEMBL1433','10469369','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that are synthesized either from the amino acid phenylalanine (phenylpropanoids) or the decarboxylative condensation of malonyl-CoA (polyketides). Phenylpropanoids are aromatic compounds based on the phenylpropane skeleton. Polyketides usually consist of alternating carbonyl and methylene groups (beta-polyketones), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000261\" rel=\"noopener\" target=\"_blank\">Phenylpropanoids and polyketides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 24 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50845\" rel=\"noopener\" target=\"_blank\">CHEBI:50845</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06973\" rel=\"noopener\" target=\"_blank\">C06973</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK07000001\" rel=\"noopener\" target=\"_blank\">LMPK07000001</a>) </span></span></dd></dl>','Tetracyclines','<p>The excretion of doxycycline by the kidney is about 40% over 72 hours in individuals with normal kidney function (creatinine clearance approximately 75 mL/min). This rate may fall as low as 1-5% over 72 hours in individuals with severe renal insufficiency (creatinine clearance below 10 mL/min). Some clinical studies have shown no major difference in serum half-life of doxycycline (range 18-22 hours) in patients with normal and severely impaired renal function. Hemodialysis does not affect serum half-life of doxycycline <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.','Tetracyclines','<li>Avoid alcohol.</li>\n<li>Avoid multivalent ions. Calcium, iron, and aluminum containing products taken up to 2 hours before and 6 hours after administration can decrease drug concentrations.</li>\n<li>Take with a full glass of water.</li>','Drugs.com Drug Page',' , Agents that produce neuromuscular block (indirect) , Alimentary Tract and Metabolism , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antiinfectives and Antiseptics for Local Oral Treatment , Antiinfectives for Systemic Use , Antiparasitic Agents , Antiprotozoals , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Drugs that are Mainly Renally Excreted , Naphthacenes , OAT1/SLC22A6 inhibitors , Photosensitizing Agents , Stomatological Preparations , Tetracyclines','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>201 °C</td><td>https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf</td></tr><tr><td>water solubility</td><td>50 mg/mL</td><td>https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf</td></tr><tr><td>logP</td><td>0.63</td><td>https://deepblue.lib.umich.edu/bitstream/handle/2027.42/64911/21954_ftp.pdf?sequence=1</td></tr><tr><td>pKa</td><td>3.09</td><td>https://www.ncbi.nlm.nih.gov/pubmed/34018</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50845\" rel=\"noopener\" target=\"_blank\">CHEBI:50845</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06973\" rel=\"noopener\" target=\"_blank\">C06973</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK07000001\" rel=\"noopener\" target=\"_blank\">LMPK07000001</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014399\" rel=\"noopener\" target=\"_blank\">HMDB0014399</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D07876\" rel=\"noopener\" target=\"_blank\">D07876</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06973\" rel=\"noopener\" target=\"_blank\">C06973</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=54671203\" rel=\"noopener\" target=\"_blank\">54671203</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506491\" rel=\"noopener\" target=\"_blank\">46506491</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.10469369.html\" rel=\"noopener\" target=\"_blank\">10469369</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50041429\" rel=\"noopener\" target=\"_blank\">50041429</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=1545992\" rel=\"noopener\" target=\"_blank\">1545992</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=50845\" rel=\"noopener\" target=\"_blank\">50845</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1433\" rel=\"noopener\" target=\"_blank\">CHEMBL1433</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000016052277\" rel=\"noopener\" target=\"_blank\">ZINC000016052277</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP001371\" rel=\"noopener\" target=\"_blank\">DAP001371</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA449415\" rel=\"noopener\" target=\"_blank\">PA449415</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/DXT\" rel=\"noopener\" target=\"_blank\">DXT</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/doxycyc.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/doxycycline.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Doxycycline\" rel=\"noopener\" target=\"_blank\">Doxycycline</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Avoid multivalent ions. Calcium, iron, and aluminum containing products taken up to 2 hours before and 6 hours after administration can decrease drug concentrations.</li>\n<li>Take with a full glass of water.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A371\">Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. [<a href=\"/articles/A371\" target=\"_blank\">Article</a>] </li><li id=\"reference-A372\">Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. [<a href=\"/articles/A372\" target=\"_blank\">Article</a>] </li><li id=\"reference-A373\">Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. [<a href=\"/articles/A373\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174025\">Bernatova S, Samek O, Pilat Z, Sery M, Jezek J, Jakl P, Siler M, Krzyzanek V, Zemanek P, Hola V, Dvorackova M, Ruzicka F: Following the mechanisms of bacteriostatic versus bactericidal action using Raman spectroscopy. Molecules. 2013 Oct 24;18(11):13188-99. doi: 10.3390/molecules181113188. [<a href=\"/articles/A174025\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174028\">Bonnetblanc JM: [Doxycycline]. Ann Dermatol Venereol. 2002 Jun-Jul;129(6-7):874-82. [<a href=\"/articles/A174028\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174031\">Valentin S, Morales A, Sanchez JL, Rivera A: Safety and efficacy of doxycycline in the treatment of rosacea. Clin Cosmet Investig Dermatol. 2009 Aug 12;2:129-40. [<a href=\"/articles/A174031\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174034\">Smilack JD: The tetracyclines. Mayo Clin Proc. 1999 Jul;74(7):727-9. doi: 10.4065/74.7.727. [<a href=\"/articles/A174034\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174037\">Weinberg JM: The anti-inflammatory effects of tetracyclines. Cutis. 2005 Apr;75(4 Suppl):6-11. [<a href=\"/articles/A174037\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174040\">Chukwudi CU: rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4433-41. doi: 10.1128/AAC.00594-16. Print 2016 Aug. [<a href=\"/articles/A174040\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174043\">Nguyen F, Starosta AL, Arenz S, Sohmen D, Donhofer A, Wilson DN: Tetracycline antibiotics and resistance mechanisms. Biol Chem. 2014 May;395(5):559-75. doi: 10.1515/hsz-2013-0292. [<a href=\"/articles/A174043\" target=\"_blank\">Article</a>] </li><li id=\"reference-A19429\">Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [<a href=\"/articles/A19429\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174046\">Laursen BS, Sorensen HP, Mortensen KK, Sperling-Petersen HU: Initiation of protein synthesis in bacteria. Microbiol Mol Biol Rev. 2005 Mar;69(1):101-23. doi: 10.1128/MMBR.69.1.101-123.2005. [<a href=\"/articles/A174046\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174070\">Xu Z, Culver GM: Differential assembly of 16S rRNA domains during 30S subunit formation. RNA. 2010 Oct;16(10):1990-2001. doi: 10.1261/rna.2246710. Epub 2010 Aug 24. [<a href=\"/articles/A174070\" target=\"_blank\">Article</a>] </li><li id=\"reference-L33330\">FDA Approved Drug Products: Vibramycin (doxycycline) for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/050006s092,050007s034,050480s058,050533s047lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-F3052\">Doxycycline MedSafe NZ [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/052/original/Doxycycline__Medsafe_NZ.pdf?1548177564\" target=\"_blank\">File</a>] </li><li id=\"reference-F3055\">Doxycycline EMA label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/055/original/oracea-article-29-referral-annex-i-ii-iii-iv_en.pdf?1548195540\" target=\"_blank\">File</a>] </li><li id=\"reference-F3073\">Antibiotics that affect the ribosome [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/073/original/06lambert5764.pdf?1548269571\" target=\"_blank\">File</a>] </li></ol>','<p>16.33 hr (± 4.53 sd) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','HMDB0014399','(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide','InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1','JBIWCJUYHHGXTC-AKNGSSGZSA-N','<p>Doxycycline is indicated for the treatment of various infections by gram-positive and gram-negative bacteria, aerobes and anaerobes, as well other types of bacteria. A complete list of organisms is available in the FDA label and in the \"indications\" section of this drug entry <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>The following are some of the major infections that may be treated with doxycycline <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>:</p><p>Rocky mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae</p><p>Respiratory tract infections caused by Mycoplasma pneumoniae</p><p>Lymphogranuloma venereum caused by Chlamydia trachomatis</p><p>Psittacosis (ornithosis) caused by Chlamydia psittaci</p><p>Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence</p><p>Inclusion conjunctivitis caused by Chlamydia trachomatis</p><p>Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis</p><p>Nongonococcal urethritis caused by Ureaplasma urealyticum</p><p>Relapsing fever due to Borrelia recurrentis</p><p><strong>A note regarding anti-microbial resistance</strong></p><p>It is important to note that doxycycline is not the drug of choice in the treatment of any type of staphylococcal infection.\nUp to 44 percent of strains of Streptococcus pyogenes and 74 percent of Streptococcus faecalis have been found to be resistant to tetracyclines. Therefore, tetracyclines such as doxycycline should not be used to treat streptococcal infections unless the microorganism has been demonstrated to be susceptible <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','C06973','D07876','Organic compounds','<p>Doxycycline is metabolized in the liver and gastrointestinal tract and concentrated in bile <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline EMA label\" href=\"#reference-F3055\">16</a></sup>.\nMajor metabolic pathways of doxycycline have not been identified, however, enzyme inducers have been found to decrease the half-life of doxycycline <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline EMA label\" href=\"#reference-F3055\">16</a></sup>.</p>','Aromatic homopolycyclic compounds','DXT','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000291?highlight[compounds][]=DB00254&amp;highlight[proteins][]=DB00254\">Doxycycline Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449415','<p>&gt;90% <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline EMA label\" href=\"#reference-F3055\">16</a></sup>.</p>','54671203','46506491','<p>Mainly the urine and feces as active and unchanged drug <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Between 40% and 60% of an administered dose can be accounted for in the urine by 92 hours, and approximately 30% can be accounted for in the feces <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline EMA label\" href=\"#reference-F3055\">16</a></sup>.</p>','RxList Drug Page','1545992','[H][C@@]12[C@@H](C)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 24 more</a>','Phenylpropanoids and polyketides','<span class=\"citations\"><p>Dai-Wu Seol, \"DNA cassette for the production of secretable recombinant trimeric TRAIL proteins, tetracycline/ doxycycline-inducible adeno-associated virus vector, their combination and use in gene therapy.\" U.S. Patent US20020128438, issued September 12, 2002.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20020128438&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20020128438</a>','DAP001371','<p>There are various precautions to be undertaken while doxycyline is administered <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>. A full list of adverse events is included in the \"Adverse Effects\" section of this drug entry.</p><p><strong>A note on tooth development and tetracycline use</strong></p><p>The use of tetracyclines, including doxycycline, during tooth development (i.e. the last half of pregnancy, throughout infancy, and in childhood up to 8 years of age) may lead to tooth enamel hypoplasia and yellow-gray discoloration of teeth. It is advisable not to administer doxycycline in this age group according to the FDA label, except for in cases of post-exposure cases of anthrax (including inhalational anthrax) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Other sources state that doxycycline should not be administered in children under 12 years <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p><p><strong>A note on Clostridium difficile</strong>\nClostridium difficile associated diarrhea (CDAD) and antibiotic associated pseudomembranous colitis may result from doxycycline use. Administering antibacterial agents changes the normal flora of the colon leading to an overgrowth of C. difficile. This bacteria produces toxins A and B, which contribute to the development of CDAD <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>. in moderate to severe cases, therapy with a suitable oral antibacterial agent effective against Clostridium difficile should be considered. Fluids, electrolytes and protein replacement should be provided when warranted <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p><p><strong>A note on gastrointestinal irritation</strong>\nGastrointestinal irritation may also occur. Rarely, esophagitis and esophageal ulcers have been reported in patients receiving doxycycline. Most of these patients took medication immediately before going to bed. Administration of appropriate amounts of fluid with the tablets is recommended to reduce the risk of esophageal irritation and ulceration, and late evening ingestion of the dose should be avoided <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>. To decrease the risk of gastric irritation, it is recommended that doxycycline is taken with food or milk. The absorption of doxycycline is not significantly influenced by simultaneous ingestion of food or milk <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p><p><strong>Pregnancy</strong>\nResults of animal research indicate that tetracyclines cross the placenta, are found in fetal tissues and exert toxic effects on the developing fetus, manifested by retardation of skeletal development. The importance of this in humans is not known, however, doxycycline should not be used in pregnant women unless the benefit significantly outweighs the risk <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>. </p><p><strong>Carcinogenicity</strong>\nIn vivo studies conducted in rats and mice have not provided conclusive evidence that tetracyclines may be carcinogenic or that they affect fertility. In two mammalian cell lines, positive tests for mutagenicity occurred at concentrations of 60 and 10 mcg/ml respectively. In humans, no association between tetracyclines and these effects have been established <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p>','334895S862','<p>Doxycycline diffuses readily into most body tissues, fluid and/or cavities and the volume of distribution has been measured as 0.7 L/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Doxycycline MedSafe NZ\" href=\"#reference-F3052\">15</a></sup>.</p>','Doxycycline','ZINC000016052277'),(22,'Theophylline','theophylline','Theophylline is a xanthine used to manage the symptoms of asthma, COPD, and other lung conditions caused by reversible airflow obstruction.','Elixophyllin, Elixophylline, Pulmophylline, Quibron-T, Theo-24, Theolair, Uniphyl','Theophylline','<p>A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD.</p>','C7H8N4O2','DB00277','Approved','Small Molecule','Average: 180.164 Monoisotopic: 180.06472552 ',' , R03DA — Xanthines , R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R — RESPIRATORY SYSTEM , R03DA — Xanthines , R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R — RESPIRATORY SYSTEM , R03DA — Xanthines , R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R — RESPIRATORY SYSTEM , R03DA — Xanthines , R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R — RESPIRATORY SYSTEM , R03DB — Xanthines and adrenergics , R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES , R — RESPIRATORY SYSTEM','<p>Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Purines that carry a C=O group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001505\" rel=\"noopener\" target=\"_blank\">6-oxopurines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000291\" rel=\"noopener\" target=\"_blank\">Pyrimidones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000078\" rel=\"noopener\" target=\"_blank\">Imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing two amine groups joined by a carbonyl (C=O) functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000517\" rel=\"noopener\" target=\"_blank\">Ureas</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 1A2-2964(G/A)(A;A) / (G;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of theophylline.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 1A2-2964(G/A)(A;A) / (G;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of theophylline.Details','10847','58-55-9','28177','CHEMBL190','2068','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic polycyclic compounds containing an imidazole ring fused to a pyrimidine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001797\" rel=\"noopener\" target=\"_blank\">Imidazopyrimidines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000245\" rel=\"noopener\" target=\"_blank\">Purines and purine derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000247\" rel=\"noopener\" target=\"_blank\">Xanthines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Purines that carry a C=O group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001505\" rel=\"noopener\" target=\"_blank\">6-oxopurines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000291\" rel=\"noopener\" target=\"_blank\">Pyrimidones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000078\" rel=\"noopener\" target=\"_blank\">Imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing two amine groups joined by a carbonyl (C=O) functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000517\" rel=\"noopener\" target=\"_blank\">Ureas</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">6-oxopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkaloid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Urea</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Xanthine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 11 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dimethylxanthine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28177\" rel=\"noopener\" target=\"_blank\">CHEBI:28177</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Purine alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07130\" rel=\"noopener\" target=\"_blank\">C07130</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a small molecule (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-12479\" rel=\"noopener\" target=\"_blank\">CPD-12479</a>) </span></span></dd></dl>','Imidazopyrimidines','','This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.','Xanthines','<li>Avoid excessive or chronic alcohol consumption. Ingesting alcohol may reduce the clearance, and therefore increase the serum concentrations of theophylline.</li>\n<li>Avoid St. John\'s Wort.</li>\n<li>Take with or without food. Take consistently with regard to food.</li>','Drugs.com Drug Page',' , Agents that reduce seizure threshold , Alkaloids , Anti-Asthmatic Agents , Autonomic Agents , Bronchodilator Agents , Cardiovascular Agents , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2E1 Substrates , Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Substrates , Drugs for Obstructive Airway Diseases , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Narrow Therapeutic Index Drugs , Neurotransmitter Agents , Peripheral Nervous System Agents , Phosphodiesterase 5 Inhibitors , Phosphodiesterase Inhibitors , Purinergic Agents , Purinergic Antagonists , Purinergic P1 Receptor Antagonists , Purines , Purinones , Respiratory Smooth Muscle Relaxants , Respiratory System Agents , Vasodilating Agents , Xanthine derivatives , Xanthines and Adrenergics','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>273 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>7360 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; HE,Y (2003)</td></tr><tr><td>logP</td><td>-0.02</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>Caco2 permeability</td><td>-4.35</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>8.81</td><td>KORTUM,G ET AL (1961)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dimethylxanthine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28177\" rel=\"noopener\" target=\"_blank\">CHEBI:28177</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Purine alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07130\" rel=\"noopener\" target=\"_blank\">C07130</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a small molecule (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-12479\" rel=\"noopener\" target=\"_blank\">CPD-12479</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0001889\" rel=\"noopener\" target=\"_blank\">HMDB0001889</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00371\" rel=\"noopener\" target=\"_blank\">D00371</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07130\" rel=\"noopener\" target=\"_blank\">C07130</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2153\" rel=\"noopener\" target=\"_blank\">2153</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505949\" rel=\"noopener\" target=\"_blank\">46505949</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.2068.html\" rel=\"noopener\" target=\"_blank\">2068</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=10847\" rel=\"noopener\" target=\"_blank\">10847</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=10438\" rel=\"noopener\" target=\"_blank\">10438</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28177\" rel=\"noopener\" target=\"_blank\">28177</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL190\" rel=\"noopener\" target=\"_blank\">CHEMBL190</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000018043251\" rel=\"noopener\" target=\"_blank\">ZINC000018043251</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000002\" rel=\"noopener\" target=\"_blank\">DAP000002</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451647\" rel=\"noopener\" target=\"_blank\">PA451647</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=413\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/TEP\" rel=\"noopener\" target=\"_blank\">TEP</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/theosr.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/theophylline.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/the1440.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Theophylline\" rel=\"noopener\" target=\"_blank\">Theophylline</a></dd></dl>','<li>Avoid excessive or chronic alcohol consumption. Ingesting alcohol may reduce the clearance, and therefore increase the serum concentrations of theophylline.</li>\n<li>Avoid St. John\'s Wort.</li>\n<li>Take with or without food. Take consistently with regard to food.</li>','<span class=\"not-available\">Not Available</span>','<p>8 hours</p>','HMDB0001889','1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione','InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)','ZFXYFBGIUFBOJW-UHFFFAOYSA-N','<p>For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis.</p>','C07130','D00371','Organic compounds','<p>Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','TEP','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000028?highlight[compounds][]=DB00277&amp;highlight[proteins][]=DB00277\">Caffeine Metabolism</a></td><td>Metabolic</td></tr></tbody>','PA451647','<p>40%, primarily to albumin.</p>','2153','46505949','<p>Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults.</p>','RxList Drug Page','10438','CN1C2=C(NC=N2)C(=O)N(C)C1=O','Solid','Purines and purine derivatives','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">6-oxopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkaloid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Urea</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Xanthine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 11 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Nicolae S. Bodor, Kenneth B. Sloan, Yu-Neng Kuo, \"Method for synthesizing certain selected pro-drug forms of theophylline.\" U.S. Patent US4000132, issued January, 1956.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4000132&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4000132</a>','DAP000002','<p>Symptoms of overdose include seizures, arrhythmias, and GI effects.</p>','0I55128JYK','','Theophylline','ZINC000018043251'),(23,'Morphine','morphine','Morphine is an opioid agonist used for the relief of moderate to severe acute and chronic pain.','Arymo, Avinza, Doloral, Duramorph, Embeda, Infumorph, Kadian, M-ediat, M-eslon, MSIR, Mitigo, Ms Contin, Statex','Morphine','<p>Morphine, the main alkaloid of opium, was first obtained from poppy seeds in 1805.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pacifici GM: Metabolism and pharmacokinetics of morphine in neonates: A review. Clinics (Sao Paulo). 2016 Aug;71(8):474-80. doi: 10.6061/clinics/2016(08)11. (PubMed ID 27626479)\" href=\"#reference-A176035\">1</a></sup> It is a potent analgesic, though its use is limited due to tolerance, withdrawal, and the risk of abuse.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kim J, Ham S, Hong H, Moon C, Im HI: Brain Reward Circuits in Morphine Addiction. Mol Cells. 2016 Sep;39(9):645-53. doi: 10.14348/molcells.2016.0137. Epub 2016 Aug 9. (PubMed ID 27506251)\" href=\"#reference-A176050\">2</a></sup> Morphine is still routinely used today, though there are a number of semi-synthetic opioids of varying strength such as <a href=\"https://go.drugbank.com/drugs/DB00318\">codeine</a>, <a href=\"https://go.drugbank.com/drugs/DB00813\">fentanyl</a>, <a href=\"https://go.drugbank.com/drugs/DB00333\">methadone</a>, <a href=\"https://go.drugbank.com/drugs/DB00956\">hydrocodone</a>, <a href=\"https://go.drugbank.com/drugs/DB00327\">hydromorphone</a>, <a href=\"https://go.drugbank.com/drugs/DB00454\">meperidine</a>, and <a href=\"https://go.drugbank.com/drugs/DB00497\">oxycodone</a>.</p><p>Morphine was granted FDA approval in 1941.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Morphine Sulfate Oral Tablets\" href=\"#reference-L12114\">13</a></sup></p>','C17H19NO3','DB00295','Approved, Investigational','Small Molecule','Average: 285.3377 Monoisotopic: 285.136493479 ',' , A07DA — Antipropulsives , A07D — ANTIPROPULSIVES , A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS , A — ALIMENTARY TRACT AND METABOLISM , N02AA — Natural opium alkaloids , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM , N02AA — Natural opium alkaloids , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM , N02AG — Opioids in combination with antispasmodics , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM','<p>Morphine is absorbed in the alkaline environments of the upper intestine and rectal mucosa.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. (PubMed ID 2245160)\" href=\"#reference-A176119\">6</a></sup> The bioavailability of morphine is 80-100%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. (PubMed ID 10718775)\" href=\"#reference-A176164\">8</a></sup> There is significant first-pass metabolism, therefore oral doses are 6 times larger than parenteral doses to achieve the same effect. Morphine reaches steady-state concentrations after 24-48 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pacifici GM: Metabolism and pharmacokinetics of morphine in neonates: A review. Clinics (Sao Paulo). 2016 Aug;71(8):474-80. doi: 10.6061/clinics/2016(08)11. (PubMed ID 27626479)\" href=\"#reference-A176035\">1</a></sup> Parenteral morphine has a T<sub>max</sub> of 15 minutes and oral morphine has a T<sub>max</sub> of 90 minutes, with a C<sub>max</sub> of 283nmol/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Glare PA, Walsh TD: Clinical pharmacokinetics of morphine. Ther Drug Monit. 1991 Jan;13(1):1-23. (PubMed ID 2057987)\" href=\"#reference-A176122\">7</a>,<a class=\"reference-popover-link\" data-content=\"Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. (PubMed ID 10718775)\" href=\"#reference-A176164\">8</a></sup> The AUC of morphine is 225-290nmol*h/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. (PubMed ID 10718775)\" href=\"#reference-A176164\">8</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000025\" rel=\"noopener\" target=\"_blank\">Phenanthrenes and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004189\" rel=\"noopener\" target=\"_blank\">Coumarans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000195\" rel=\"noopener\" target=\"_blank\">Piperidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 3 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsMultidrug resistance protein 1---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.DetailsMu-type opioid receptor---(A;A)A AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsMultidrug resistance protein 1---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.DetailsMu-type opioid receptor---(A;A)A AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.Details','50000092','57-27-2','17303','CHEMBL70','4450907','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000058\" rel=\"noopener\" target=\"_blank\">Morphinans</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000058\" rel=\"noopener\" target=\"_blank\">Morphinans</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000025\" rel=\"noopener\" target=\"_blank\">Phenanthrenes and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004189\" rel=\"noopener\" target=\"_blank\">Coumarans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000195\" rel=\"noopener\" target=\"_blank\">Piperidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 3 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Coumaran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Morphinan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenanthrene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Piperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 15 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">morphinane alkaloid, organic heteropentacyclic compound (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17303\" rel=\"noopener\" target=\"_blank\">CHEBI:17303</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Alkaloids, Isoquinoline alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01516\" rel=\"noopener\" target=\"_blank\">C01516</a>) </span></span></dd></dl>','Morphinans','<p>The apparent clearance of intravenous or subcutaneous morphine is 1600 mL/min.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. (PubMed ID 10718775)\" href=\"#reference-A176164\">8</a></sup></p>','This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.','Morphinans','<li>Avoid alcohol. Concomitant use may lead to profound sedation, respiratory depression, coma, and death.</li>\n<li>Take with or without food. There is no significant different in the AUC or Cmax of oral extended release tablets when taken with or without food.</li>','Drugs.com Drug Page',' , Alkaloids , Analgesics , Anesthetics , Central Nervous System Agents , Central Nervous System Depressants , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Substrates , Heterocyclic Compounds, Fused-Ring , High-risk opioids , Hypotensive Agents , Narcotics , Natural Opium Alkaloids , Nervous System , Neuraxial Anesthetics , Opiate Agonists , Opiate Alkaloids , Opioid Agonist , Opioids , P-glycoprotein substrates , Peripheral Nervous System Agents , Phenanthrenes , Sensory System Agents , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome , UGT1A1 Substrates , UGT1A3 substrates , UGT2B7 substrates','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>255 °C</td><td>MSDS</td></tr><tr><td>boiling point (°C)</td><td>190ºC</td><td>Lide DR. CRC Handbook of Chemistry. 2004 </td></tr><tr><td>water solubility</td><td>149 mg/L (at 20 °C)</td><td>MSDS</td></tr><tr><td>logP</td><td>0.87</td><td>Agilent Technology. LC/MS/MS Analysis of Opiates. </td></tr><tr><td>pKa</td><td>8.21 (at 25 °C)</td><td>Agilent Technology. LC/MS/MS Analysis of Opiates. </td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">morphinane alkaloid, organic heteropentacyclic compound (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17303\" rel=\"noopener\" target=\"_blank\">CHEBI:17303</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Alkaloids, Isoquinoline alkaloids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01516\" rel=\"noopener\" target=\"_blank\">C01516</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014440\" rel=\"noopener\" target=\"_blank\">HMDB0014440</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D08233\" rel=\"noopener\" target=\"_blank\">D08233</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01516\" rel=\"noopener\" target=\"_blank\">C01516</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5288826\" rel=\"noopener\" target=\"_blank\">5288826</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505161\" rel=\"noopener\" target=\"_blank\">46505161</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.4450907.html\" rel=\"noopener\" target=\"_blank\">4450907</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50000092\" rel=\"noopener\" target=\"_blank\">50000092</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=7052\" rel=\"noopener\" target=\"_blank\">7052</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17303\" rel=\"noopener\" target=\"_blank\">17303</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL70\" rel=\"noopener\" target=\"_blank\">CHEMBL70</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003812983\" rel=\"noopener\" target=\"_blank\">ZINC000003812983</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000071\" rel=\"noopener\" target=\"_blank\">DAP000071</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450550\" rel=\"noopener\" target=\"_blank\">PA450550</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/MOI\" rel=\"noopener\" target=\"_blank\">MOI</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/ms.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/morphine.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/msc1277.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Morphine\" rel=\"noopener\" target=\"_blank\">Morphine</a></dd></dl>','<li>Avoid alcohol. Concomitant use may lead to profound sedation, respiratory depression, coma, and death.</li>\n<li>Take with or without food. There is no significant different in the AUC or Cmax of oral extended release tablets when taken with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A176035\">Pacifici GM: Metabolism and pharmacokinetics of morphine in neonates: A review. Clinics (Sao Paulo). 2016 Aug;71(8):474-80. doi: 10.6061/clinics/2016(08)11. [<a href=\"/articles/A176035\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176050\">Kim J, Ham S, Hong H, Moon C, Im HI: Brain Reward Circuits in Morphine Addiction. Mol Cells. 2016 Sep;39(9):645-53. doi: 10.14348/molcells.2016.0137. Epub 2016 Aug 9. [<a href=\"/articles/A176050\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176056\">Beltran-Campos V, Silva-Vera M, Garcia-Campos ML, Diaz-Cintra S: Effects of morphine on brain plasticity. Neurologia. 2015 Apr;30(3):176-80. doi: 10.1016/j.nrl.2014.08.004. Epub 2014 Nov 11. [<a href=\"/articles/A176056\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176059\">Klimas R, Mikus G: Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. Br J Anaesth. 2014 Dec;113(6):935-44. doi: 10.1093/bja/aeu186. Epub 2014 Jul 1. [<a href=\"/articles/A176059\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176116\">Lotsch J: Pharmacokinetic-pharmacodynamic modeling of opioids. J Pain Symptom Manage. 2005 May;29(5 Suppl):S90-103. doi: 10.1016/j.jpainsymman.2005.01.012. [<a href=\"/articles/A176116\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176119\">Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. [<a href=\"/articles/A176119\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176122\">Glare PA, Walsh TD: Clinical pharmacokinetics of morphine. Ther Drug Monit. 1991 Jan;13(1):1-23. [<a href=\"/articles/A176122\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176164\">Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. [<a href=\"/articles/A176164\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176167\">Shigeev S: Severity of opiate intoxication to gender and age. Soud Lek. 2007 Jan;52(1):21-4. [<a href=\"/articles/A176167\" target=\"_blank\">Article</a>] </li><li id=\"reference-L5713\">FDA approvals [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=018565\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5728\">NIH [<a href=\"https://medlineplus.gov/magazine/issues/spring11/articles/spring11pg9.html\" target=\"_blank\">Link</a>] </li><li id=\"reference-L12108\">FDA Approved Drug Products: Infumorph Morphine Sulfate Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018565s024lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L12114\">FDA Approved Drug Products: Morphine Sulfate Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022207s009lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L35490\">FDA Approved Drug Products: Morphine Sulfate Oral Solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/022195s020lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L35495\">FDA Approved Drug Products: MS Contin (Morphine Sulfate) Oral Extended Release Tablet [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/019516s057lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L35500\">FDA Approved Drug Products: Kadian (Morphine Sulfate) Oral Extended Release Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020616s065lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>Morphine has a half life of 2-3 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lotsch J: Pharmacokinetic-pharmacodynamic modeling of opioids. J Pain Symptom Manage. 2005 May;29(5 Suppl):S90-103. doi: 10.1016/j.jpainsymman.2005.01.012. (PubMed ID 15907650)\" href=\"#reference-A176116\">5</a></sup></p>','HMDB0014440','(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol','InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1','BQJCRHHNABKAKU-KBQPJGBKSA-N','<p>Morphine is used for the management of chronic, moderate to severe pain.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kim J, Ham S, Hong H, Moon C, Im HI: Brain Reward Circuits in Morphine Addiction. Mol Cells. 2016 Sep;39(9):645-53. doi: 10.14348/molcells.2016.0137. Epub 2016 Aug 9. (PubMed ID 27506251)\" href=\"#reference-A176050\">2</a></sup></p><p>Opiods, including morphine, are effective for the short term management of pain. Patients taking opioids long term may need to be monitored for the development of physical dependence, addiction disorder, and drug abuse.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"NIH\" href=\"#reference-L5728\">11</a></sup></p>','C01516','D08233','Organic compounds','<p>Morphine is 90% metabolized by glucuronidation by UGT2B7 and sulfation at positions 3 and 6.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klimas R, Mikus G: Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. Br J Anaesth. 2014 Dec;113(6):935-44. doi: 10.1093/bja/aeu186. Epub 2014 Jul 1. (PubMed ID 24985077)\" href=\"#reference-A176059\">4</a></sup> Morphine can also be metabolized to codeine, normorphine, and morphine ethereal sulfate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. (PubMed ID 2245160)\" href=\"#reference-A176119\">6</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','MOI','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000406?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Morphine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000405?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Codeine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000623?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Heroin Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000407?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Heroin Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000621?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Codeine Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000622?highlight[compounds][]=DB00295&amp;highlight[proteins][]=DB00295\">Morphine Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA450550','<p>Morphine is 35% protein bound, the metabolite morphine-3-glucuronide is 10% protein bound, and morphine-6-glucuronide is 15% protein bound.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klimas R, Mikus G: Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. Br J Anaesth. 2014 Dec;113(6):935-44. doi: 10.1093/bja/aeu186. Epub 2014 Jul 1. (PubMed ID 24985077)\" href=\"#reference-A176059\">4</a></sup></p>','5288826','46505161','<p>70-80% of an administered dose is excreted within 48 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. (PubMed ID 2245160)\" href=\"#reference-A176119\">6</a></sup> Morphine is predominantly eliminated in the urine with 2-10% of a dose recovered as the unchanged parent drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klimas R, Mikus G: Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. Br J Anaesth. 2014 Dec;113(6):935-44. doi: 10.1093/bja/aeu186. Epub 2014 Jul 1. (PubMed ID 24985077)\" href=\"#reference-A176059\">4</a></sup> 7-10% of a dose of morphine is eliminated in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Morphine Sulfate Oral Tablets\" href=\"#reference-L12114\">13</a></sup></p>','RxList Drug Page','7052','[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Coumaran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Morphinan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenanthrene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Piperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 15 more</a>','Alkaloids and derivatives','<a href=\"https://www.google.com/?tbm=pts#q=4764615&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4764615</a>','DAP000071','<p>The LD<sub>50</sub> is 0.78µg/mL in males and 0.98µg/mL in females.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Shigeev S: Severity of opiate intoxication to gender and age. Soud Lek. 2007 Jan;52(1):21-4. (PubMed ID 17370507)\" href=\"#reference-A176167\">9</a></sup></p><p>Patients experiencing an overdose present with respiratory depression, somnolence, skeletal muscle flaccidity, cold and clammy skin, miosis, and mydriasis. Symptoms of overdose can progress to pulmonary edema, bradycardia, hypotension, cardiac arrest, and death.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Infumorph Morphine Sulfate Injection\" href=\"#reference-L12108\">12</a></sup> Treat overdose with symptomatic and supportive treatment which may include the use of oxygen, vasopressors, and naloxone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Infumorph Morphine Sulfate Injection\" href=\"#reference-L12108\">12</a></sup></p>','76I7G6D29C','<p>The volume of distribution of morphine is 5.31L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. (PubMed ID 2245160)\" href=\"#reference-A176119\">6</a></sup> Morphine-6-glucuronide has a volume of distribution of 3.61L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. (PubMed ID 2245160)\" href=\"#reference-A176119\">6</a></sup></p>','Morphine','ZINC000003812983'),