Cocaine metabolism (Homo sapiens)
From WikiPathways
Description
Cocaine is rapidly metabolized to major metabolites, benzoylecgonine and ecgonine methyl ester and minor metabolites, norcocaine, p-hydroxycocaine, m-hydroxycocaine, p-hydroxybenzoylecgonine (pOHBE),and rn-hydroxybenzoylecgonine. (http://jat.oxfordjournals.org/content/30/8/501.long)
Quality Tags
Ontology Terms
Saving...Bibliography
- Schneider KJ, DeCaprio AP; ''Evaluation of in vitro metabolic systems for common drugs of abuse. 1. Cocaine.''; Xenobiotica, 2013 PubMed Europe PMC Scholia
- Kolbrich EA, Barnes AJ, Gorelick DA, Boyd SJ, Cone EJ, Huestis MA; ''Major and minor metabolites of cocaine in human plasma following controlled subcutaneous cocaine administration.''; J Anal Toxicol, 2006 PubMed Europe PMC Scholia
- Maurer HH, Sauer C, Theobald DS; ''Toxicokinetics of drugs of abuse: current knowledge of the isoenzymes involved in the human metabolism of tetrahydrocannabinol, cocaine, heroin, morphine, and codeine.''; Ther Drug Monit, 2006 PubMed Europe PMC Scholia
- Watanabe K, Hida Y, Matsunaga T, Yamamoto I, Yoshimura H; ''Formation of p-hydroxycocaine from cocaine by hepatic microsomes of animals and its pharmacological effects in mice.''; Biol Pharm Bull, 1993 PubMed Europe PMC Scholia
- Kloss MW, Rosen GM, Rauckman EJ; ''N-demethylation of cocaine to norcocaine. Evidence for participation by cytochrome P-450 and FAD-containing monooxygenase.''; Mol Pharmacol, 1983 PubMed Europe PMC Scholia
History
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External references
DataNodes
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| Name | Type | Database reference | Comment |
|---|---|---|---|
| Benzoylecgonine | Metabolite | 395095 (Chemspider)  | |
| Benzoylnorecgonine | Metabolite | Q27281213 (Wikidata) | |
| CYP-450 | Protein | IPR0011 (InterPro) | cytochrome P450 |
| CYP3A4 | GeneProduct | ENSG00000160868 (Ensembl) | part of oxidative metabolism, N-demethylation |
| Cocaethylene | Metabolite | Q4586731 (Wikidata) | toxic metabolite |
| Cocaine-N-oxide | Metabolite | 72182-46-8 (CAS) | |
| Cocaine | Metabolite | 10194104 (Chemspider) | |
| Crack cocaine | Metabolite | Q330694 (Wikidata) | frecrack is the free base form of cocaine |
| Ecgonidine | Metabolite | Q5332352 (Wikidata) | anhydroecgonine |
| Ecgonine ethyl ester | Metabolite | 391939 (Chemspider) | |
| Ecgonine methyl ester | Metabolite | 391939 (Chemspider) | |
| Ethanol | Metabolite | HMDB0000108 (HMDB) | |
| Ethyl ecgonidine | Metabolite | 129847219 (PubChem-compound) | anhydroecgonine ethyl ester |
| FMO | Protein | 1.14.13.8 (Enzyme Nomenclature) | flavin-containing monooxygenase |
| Methylecgonidine | Metabolite | Q10858037 (Wikidata) | anhydroecgonine methylester |
| Nor-ecgonidine | Metabolite | Q82115307 (Wikidata) | noranhydroecgonine ; chemical annotation based on structural drawing in PMID:8570014 . Using CDK-depict (based on WikiPedia entry https://en.wikipedia.org/wiki/Ecgonidine). SMILES: CN1C2CCC1C(=CC2)C(=O)OC . Corresponding Inchi (with ChemAI) : InChI=1S/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3
Corresponding InChIKey (from CACTUS): MPSNEAHFGOEKBI-UHFFFAOYSA-N Through Scholia, landed at stable ID (was missing name): https://www.wikidata.org/wiki/Q82115307 |
| Norcocaethylene | Metabolite | 126246 (PubChem-compound) | |
| Norcocaine | Metabolite | 559083 (Chemspider) | |
| P-Hydroxybenzoylecgonine | Metabolite | 90899-22-2 (CAS) | |
| Pseudo-ChE | Protein | ENSG00000114200 (Ensembl) | pseudocholinesterase |
| hCE1 | Protein | P23141 (Uniprot-TrEMBL) | human carboxylesterase-1 |
| hCE2 | Protein | O00748 (Uniprot-TrEMBL) | human carboxylesterase-2 |
| m-Hydroxybenzoylecgonine | Metabolite | 15607453 (Chemspider) | |
| m-hydroxycocaine | Metabolite | 26502800 (Chemspider) | |
| p-hydroxycocaine | Metabolite | 26502800 (Chemspider) |
Annotated Interactions
No annotated interactions
