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

General Information of Drug (ID: DR1379)
Drug Name
Quinidine
Synonyms
Quinact; Quinaglute; Quinalan; Quinatime; Quindine; Quinicardine; Quinidex; Quinidine sulfate; Quiniduran; Quinora; beta-Quinine; Cardioquin; Chinidin; Chinidine; Cin-Quin; Cinchonan-9-ol, 6'-methoxy-, (9S)-; Conchinin; Conchinine; Conquinine; Duraquin; ITX08688JL; Kinidin; Pitayine; chinidinum; quinidina; quinidine; (+)-Quinidine; (8R,9S)-Quinidine; (9S)-6'-Methoxycinchonan-9-ol; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; 56-54-2; CHEBI:28593; CHEMBL1294; MFCD00135581; UNII-ITX08688JL
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.4 Topological Polar Surface Area 45.6
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
441074
ChEBI ID
CHEBI:28593
CAS Number
56-54-2
Formula
C20H24N2O2
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
InChI
1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
InChIKey
LOUPRKONTZGTKE-LHHVKLHASA-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
2'-Quinidinone DM015873
14589192
Unclear - Unclear 1 [5]
3-OHquinidine DM015823
13217486
Oxidation - Hydroxylation 1 [5]
O-Desmethyl-Quinidine DM015769
11587639
Unclear - Unclear 1 [5]
Quinidine0,11-dihydrodiol DM018112 N. A. Unclear - Unclear 1 [5]
QuinidineN-oxide DM018111 N. A. Unclear - Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013120 Quinidine 3-OHquinidine Oxidation - Hydroxylation Unclear [5]
MR013121 Quinidine QuinidineN-oxide Unclear - Unclear Unclear [5]
MR013122 Quinidine Quinidine0,11-dihydrodiol Unclear - Unclear Unclear [5]
MR013123 Quinidine 2'-Quinidinone Unclear - Unclear Unclear [5]
MR013124 Quinidine O-Desmethyl-Quinidine Unclear - Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Quinidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
3 Effect of diclofenac, disulfiram, itraconazole, grapefruit juice and erythromycin on the pharmacokinetics of quinidine. Br J Clin Pharmacol. 1999 Dec;48(6):829-38.
4 Binding of quinidine radically increases the stability and decreases the flexibility of the cytochrome P450 2D6 active site. J Inorg Biochem. 2012 May;110:46-50.
5 In vitro metabolism of quinidine: the (3S)-3-hydroxylation of quinidine is a specific marker reaction for cytochrome P-4503A4 activity in human liver microsomes. J Pharmacol Exp Ther. 1999 Apr;289(1):31-7.
6 10th North American ISSX meeting. October 24-28, 2000. Indianapolis, Indiana, USA. Abstracts. Drug Metab Rev. 2000;32 Suppl 2:137-340.
7 Drug Interactions Flockhart Table

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.