Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0365)
Drug Name
Cocaine
Synonyms
Cholly; Cocain; Cocaina; Cocaine free base; Cocaine, l-; Corine; Dama blanca; Eritroxilina; Erytroxylin; Gold dust; Happy dust; Bazooka; Benzoylmethylecgonine; Bernice; Bernies; Burese; Kokain; Kokayeen; L-Cocaine; Methyl Benzoylecgonine; Neurocaine; Nose candy; Pimp's drug; Sleighride; Star dust; Star-spangled powder; White girl or lady; beta-Cocain; cocaine; cocainum; l-Cocain; (-)-Cocaine; 1-Cocaine; 2-beta-Carbomethoxy-3-beta-benzoxytropane; 50-36-2; CHEBI:27958; Cecil; Coke; Girl; HSDB 6469; I5Y540LHVR; Kokan; Leaf; Rock; Snow; UNII-I5Y540LHVR
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 303.35 Topological Polar Surface Area 55.8
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
446220
PubChem SID
4603 ; 822487 ; 830115 ; 841206 ; 7886706 ; 7978982 ; 10299853 ; 10317514 ; 14717642 ; 14849677 ; 16061210 ; 23856122 ; 24875114 ; 24882022 ; 24893116 ; 36511843 ; 46392192 ; 46392962 ; 46506326 ; 49846233 ; 53786861 ; 57404730 ; 57651790 ; 78299047 ; 85756453 ; 92718042 ; 104636021 ; 123092435 ; 126621786 ; 129937523 ; 134971337 ; 135652677 ; 137001236 ; 152104973 ; 162220988 ; 175266196 ; 175443665 ; 179252632 ; 226411107 ; 241088610 ; 250229865 ; 250231451
ChEBI ID
ChEBI:27958
CAS Number
50-36-2
TTD Drug ID
D04XPW
Formula
C17H21NO4
Canonical SMILES
CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChI
1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
InChIKey
ZPUCINDJVBIVPJ-LJISPDSOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
BE DM003685 N. A. Unclear 1 [7]
Benzoylecgonine DM003693
448223
Spontaneous - Spontaneous 1 [7] , [8]
Cocaethylene DM003695
644006
Unclear 1 [7]
Cocaine DM003698
446220
Oxidation - N-demethylation 1 [7]
Cocaine-N-oxide DM003701
156037
Oxidation - Oxidationn 1 [7]
Ecgonine methyl ester DM003690
104904
Unclear 1 [7] , [8]
M-Hydroxycocaine DM003699
11823332
Oxidation - Oxidationn 1 [7]
Norcocaine DM003697
644007
Unclear 1 [7]
p-Hydroxycocaine DM003700
10687097
Oxidation - Oxidationn 1 [7]
AEME DM003691
119478
Unclear 2 [7]
Benzoylnorecgonine DM003694
114718
Unclear 2 [7]
Cocaethylene DM003695
644006
Unclear 2 [7]
EGC DM003686
91460
Unclear 2 [7]
EME DM003692
443844
Unclear 2 [7]
MHOBE DM003688
448357
Oxidation - Oxidationn 2 [7]
Norcocaethylene DM003696
126246
Unclear 2 [7]
PHOBE DM003689
56667780
Oxidation - Oxidationn 2 [7]
AECG DM003687
101709
Unclear 3 [7]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004074 Cocaine BE Unclear Unclear [7]
MR004079 Cocaine Ecgonine methyl ester Unclear BCHE [7], [8]
MR004083 Cocaine Benzoylecgonine Spontaneous - Spontaneous Unclear [7], [8]
MR004085 Cocaine Cocaethylene Unclear Unclear [7]
MR004087 Cocaine Norcocaine Unclear Unclear [7]
MR004090 Cocaine Cocaine Oxidation - N-demethylation CYP3A4 [7]
MR004091 Cocaine M-Hydroxycocaine Oxidation - Oxidationn Unclear [7]
MR004092 Cocaine p-Hydroxycocaine Oxidation - Oxidationn Unclear [7]
MR004093 Cocaine Cocaine-N-oxide Oxidation - Oxidationn Unclear [7]
MR004075 BE EGC Unclear Unclear [7]
MR004077 BE MHOBE Oxidation - Oxidationn Unclear [7]
MR004078 BE PHOBE Oxidation - Oxidationn Unclear [7]
MR004084 Benzoylecgonine Benzoylnorecgonine Unclear Unclear [7]
MR004086 Cocaethylene Norcocaethylene Unclear Unclear [7]
MR004080 Ecgonine methyl ester EGC Unclear Unclear [7]
MR004081 Ecgonine methyl ester AEME Unclear Unclear [7]
MR004082 Ecgonine methyl ester EME Unclear Unclear [7]
MR004088 Norcocaine Cocaethylene Unclear Unclear [7]
MR004089 Norcocaine Benzoylnorecgonine Unclear Unclear [7]
MR004076 EGC AECG Unclear Unclear [7]
⏷ Show the Full List of 20 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6]
References
1 Cocaine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 An albumin-butyrylcholinesterase for cocaine toxicity and addiction: catalytic and pharmacokinetic properties. Chem Biol Interact. 2008 Sep 25;175(1-3):83-7.
3 Neuronal cytochrome P450IID1 (debrisoquine/sparteine-type): potent inhibition of activity by (-)-cocaine and nucleotide sequence identity to human hepatic P450 gene CYP2D6. Mol Pharmacol. 1991 Jul;40(1):63-8.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Regenerative changes in hepatic morphology and enhanced expression of CYP2B10 and CYP3A during daily administration of cocaine. Hepatology. 1996 Mar;23(3):515-23.
6 Drug Interactions Flockhart Table
7 Liquid chromatography--tandem mass spectrometry analysis of cocaine and its metabolites from blood, amniotic fluid, placental and fetal tissues: study of the metabolism and distribution of cocaine in pregnant rats
8 Accelerating cocaine metabolism as an approach to the treatment of cocaine abuse and toxicity

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