Cocaine metabolism (WP2826)

Homo sapiens

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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)

Authors

Andra Waagmeester , Egon Willighagen , Martina Summer-Kutmon , Anders Riutta , Denise Slenter , and Alex Pico

Activity

last edited

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Cited In

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Organisms

Homo sapiens

Communities

Annotations

Pathway Ontology

classic metabolic pathway cocaine drug pathway

Participants
Query Drugst.One

Label Type Compact URI Comment
cocaine-N-oxide Metabolite cas:72182-46-8
norcocaine Metabolite chemspider:559083
Cocaine Metabolite chemspider:10194104
m-Hydroxybenzoylecgonine Metabolite chemspider:15607453
ecgonine methyl ester Metabolite chemspider:391939
Methylecgonidine Metabolite wikidata:Q10858037 anhydroecgonine methylester
Ecgonidine Metabolite wikidata:Q5332352 anhydroecgonine
m-hydroxycocaine Metabolite chemspider:26502800
Benzoylecgonine Metabolite chemspider:395095
ethyl ecgonidine Metabolite pubchem.compound:129847219 anhydroecgonine ethyl ester
P-Hydroxybenzoylecgonine Metabolite cas:90899-22-2
Cocaethylene Metabolite wikidata:Q4586731 toxic metabolite
benzoylnorecgonine Metabolite wikidata:Q27281213
Ethanol Metabolite hmdb:HMDB0000108
p-hydroxycocaine Metabolite chemspider:26502800
ecgonine ethyl ester Metabolite chemspider:391939
Ethanol Metabolite hmdb:HMDB0000108
CYP3A4 GeneProduct ensembl:ENSG00000160868 part of oxidative metabolism, N-demethylation
FMO Protein eccode:1.14.13.8 flavin-containing monooxygenase
Pseudo-ChE Protein ensembl:ENSG00000114200 pseudocholinesterase
hCE2 Protein uniprot:O00748 human carboxylesterase-2
hCE1 Protein uniprot:P23141 human carboxylesterase-1
CYP-450 Protein interpro:IPR0011 cytochrome P450
hCE1 Protein uniprot:P23141 human carboxylesterase-1
hCE2 Protein uniprot:O00748 human carboxylesterase-2
hCE1 Protein uniprot:P23141 human carboxylesterase-1

References

  1. N-demethylation of cocaine to norcocaine. Evidence for participation by cytochrome P-450 and FAD-containing monooxygenase. Kloss MW, Rosen GM, Rauckman EJ. Mol Pharmacol. 1983 Mar;23(2):482–5. PubMed Europe PMC Scholia
  2. Formation of p-hydroxycocaine from cocaine by hepatic microsomes of animals and its pharmacological effects in mice. Watanabe K, Hida Y, Matsunaga T, Yamamoto I, Yoshimura H. Biol Pharm Bull. 1993 Oct;16(10):1041–3. PubMed Europe PMC Scholia
  3. Toxicokinetics of drugs of abuse: current knowledge of the isoenzymes involved in the human metabolism of tetrahydrocannabinol, cocaine, heroin, morphine, and codeine. Maurer HH, Sauer C, Theobald DS. Ther Drug Monit. 2006 Jun;28(3):447–53. PubMed Europe PMC Scholia
  4. Major and minor metabolites of cocaine in human plasma following controlled subcutaneous cocaine administration. Kolbrich EA, Barnes AJ, Gorelick DA, Boyd SJ, Cone EJ, Huestis MA. J Anal Toxicol. 2006 Oct;30(8):501–10. PubMed Europe PMC Scholia
  5. Evaluation of in vitro metabolic systems for common drugs of abuse. 1. Cocaine. Schneider KJ, DeCaprio AP. Xenobiotica. 2013 Dec;43(12):1043–54. PubMed Europe PMC Scholia