Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D03DIG
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| Former ID |
DAP000213
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| Drug Name |
Codeine
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| Synonyms |
codeine; Methylmorphine; Codeine anhydrous; Codicept; l-Codeine; Coducept; Morphine monomethyl ether; Morphine 3-methyl ether; 76-57-3; (-)-Codeine; O3-Methylmorphine; codeinum; Morphine-3-methyl ether; Codein; Norcodine, N-methyl; Norcodeine, N-methyl; CODEINE BASE; Codeine polistirex; codeina; O(3)-methylmorphine; CCRIS 7555; Morphine-3-methyl ester; HSDB 3043; UNII-UX6OWY2V7J; CHEBI:16714; EINECS 200-969-1; UX6OWY2V7J; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-; Codeine Anhydrate
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| Drug Type |
Small molecular drug
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| Indication | Pain [ICD-11: MG30-MG3Z] | Approved | [1], [2] | |
| Cough [ICD-11: MD12; ICD-10: R05; ICD-9: 786.2] | Phase 1 | [1], [3] | ||
| Therapeutic Class |
Analgesics
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| Company |
Forest Pharmaceuticals
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| Structure |
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Download2D MOL |
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| Formula |
C18H21NO3
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| Canonical SMILES |
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
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| InChI |
1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
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| InChIKey |
OROGSEYTTFOCAN-DNJOTXNNSA-N
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| CAS Number |
CAS 76-57-3
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| PubChem Compound ID | ||||
| PubChem Substance ID |
8425, 841961, 7978983, 8144934, 11039235, 14825207, 15419416, 24892429, 24892819, 28325869, 39317728, 46507764, 48413480, 48415816, 48423163, 49855816, 50881119, 53788605, 57653987, 57654027, 87544102, 92710514, 103169342, 103930322, 104000895, 117497011, 124954734, 126631803, 126678046, 128851630, 134337528, 134971680, 135650117, 137001257, 137175320, 142842434, 144207280, 152094958, 160963666, 164838528, 175268396, 175442317, 179151116, 223554832, 223680835, 223739746, 226395484, 241129665
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| ChEBI ID |
CHEBI:16714
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| ADReCS Drug ID | BADD_D00516 ; BADD_D00517 | |||
| SuperDrug ATC ID |
R05DA04
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| SuperDrug CAS ID |
cas=000076573
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [4], [5] | |||
| Metabolic Reaction | Deglucuronidation | |||
| Metabolic Effect | Increase activity | |||
| Description | Codeine can be metabolized by gut microbiota through deglucuronidation, which results in the increase of the drug's activity. | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Opioid receptor delta (OPRD1) | Target Info | Agonist | [6] |
| KEGG Pathway | cGMP-PKG signaling pathway | |||
| Sphingolipid signaling pathway | ||||
| Neuroactive ligand-receptor interaction | ||||
| Panther Pathway | Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway | |||
| Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway | ||||
| Enkephalin release | ||||
| Opioid proenkephalin pathway | ||||
| Opioid proopiomelanocortin pathway | ||||
| Reactome | Peptide ligand-binding receptors | |||
| G alpha (i) signalling events | ||||
| WikiPathways | GPCRs, Class A Rhodopsin-like | |||
| Peptide GPCRs | ||||
| GPCR ligand binding | ||||
| GPCR downstream signaling | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1673). | |||
| REF 2 | FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 074256. | |||
| REF 3 | Effects of a mu-opioid receptor agonist (codeine phosphate) on visuo-motor coordination and dynamic visual acuity in man. Br J Clin Pharmacol. 1986 Nov;22(5):507-12. | |||
| REF 4 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 5 | Predicting and Understanding the Human Microbiome's Impact on Pharmacology. Trends Pharmacol Sci. 2019 Jul;40(7):495-505. | |||
| REF 6 | Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16. | |||
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