Cocaine metabolism (Homo sapiens)

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1, 2, 51, 455151555155513511555551555regular uptakeFMOethyl ecgonidinehCE1m-hydroxycocainenorcocaethyleneP-HydroxybenzoylecgoninePseudo-ChEhCE2CYP3A4Ethanolecgonine methyl esterbenzoylnorecgoninecocaine-N-oxideCocaethylenenor-ecgonidineCocaineEcgonidineBenzoylecgoninem-HydroxybenzoylecgonineCYP-450Methylecgonidinenorcocaine55555p-hydroxycocaineecgonine ethyl esterhCE1hCE255EthanolhCE1Uptake via smoking5


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)

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Ontology Terms

 

Bibliography

  1. 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
  2. Schneider KJ, DeCaprio AP; ''Evaluation of in vitro metabolic systems for common drugs of abuse. 1. Cocaine.''; Xenobiotica, 2013 PubMed Europe PMC Scholia
  3. 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
  4. 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
  5. 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

History

View all...
CompareRevisionActionTimeUserComment
106727view13:21, 17 September 2019MaintBotHMDB identifier normalization
95176view11:57, 21 November 2017DeSlChanged layout.
95175view11:56, 21 November 2017DeSlChanged layout, added node for crack cocaine
95083view16:37, 13 November 2017DeSlAdded additional metabolites, enzymes/proteins changed layout.
95082view15:57, 13 November 2017DeSlAdded additional metabolic conversion + ezymes/proteins involved
92529view17:51, 13 June 2017AlexanderPicoUpdated layout to display all interactions
92526view14:39, 13 June 2017DeSlTrying to fix metabolite name position
89185view03:52, 23 August 2016AriuttaOntology Term : 'cocaine drug pathway' added !
89184view03:51, 23 August 2016AriuttaOntology Term : 'classic metabolic pathway' added !
88586view19:27, 11 August 2016Mkutmonfix unconnected lines
76363view09:26, 4 July 2014EgonwPeriodical save, work in progress
76211view14:31, 17 June 2014AndraModified description
76210view14:23, 17 June 2014AndraNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
BenzoylecgonineMetabolite395095 (Chemspider)
CYP-450ProteinIPR0011 (InterPro) cytochrome P450
CYP3A4GeneProductENSG00000160868 (Ensembl) part of oxidative metabolism, N-demethylation
CocaethyleneMetaboliteQ4586731 (Wikidata) toxic metabolite
CocaineMetabolite10194104 (Chemspider)
EcgonidineMetaboliteQ5332352 (Wikidata) anhydroecgonine
EthanolMetaboliteHMDB00108 (HMDB)
FMOProtein1.14.13.8 (Enzyme Nomenclature) flavin-containing monooxygenase
MethylecgonidineMetaboliteQ10858037 (Wikidata) anhydroecgonine methylester
P-HydroxybenzoylecgonineMetabolite90899-22-2 (CAS)
Pseudo-ChEProteinENSG00000114200 (Ensembl) pseudocholinesterase
benzoylnorecgonineMetaboliteQ27281213 (Wikidata)
cocaine-N-oxideMetabolite72182-46-8 (CAS)
ecgonine ethyl esterMetabolite391939 (Chemspider)
ecgonine methyl esterMetabolite391939 (Chemspider)
ethyl ecgonidineMetabolite129847219 (PubChem-compound) anhydroecgonine ethyl ester
hCE1ProteinP23141 (Uniprot-TrEMBL) human carboxylesterase-1
hCE2ProteinO00748 (Uniprot-TrEMBL) human carboxylesterase-2
m-HydroxybenzoylecgonineMetabolite15607453 (Chemspider)
m-hydroxycocaineMetabolite26502800 (Chemspider)
nor-ecgonidineMetabolitenoranhydroecgonine
norcocaethyleneMetabolite
norcocaineMetabolite559083 (Chemspider)
p-hydroxycocaineMetabolite26502800 (Chemspider)

Annotated Interactions

No annotated interactions

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