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

General Information of Drug (ID: DR3368)
Drug Name
Verapamil
Synonyms
VERAPAMIL; Iproveratril; 52-53-9; Vasolan; Dilacoran; Isoptin; Falicard; Isoptine; Isoptimo; Finoptin; Calan; Verapamilo; Verapamilum; Verapamilum [INN-Latin]; Lekoptin; Verapamilo [INN-Spanish]; Isotopin; Calcan; Tarka; D-365; Securon; Verelan; Izoptin; Verapamil [USAN:INN:BAN]; CP-16533-1; Covera-HS; Verpamil; CCRIS 6749; Verelan PM; Isoptin SR; C; Verapamil
Indication Hypertension [ICD11: BA00-BA04] Approved [1]
Coronavirus Disease 2019 (COVID-19) [ICD11: ICD11: 1D6Y] Phase 2/3 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 454.6 Topological Polar Surface Area 64
Heavy Atom Count 33 Rotatable Bond Count 13
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
2520
ChEBI ID
CHEBI:77733
CAS Number
52-53-9
TTD Drug ID
D06ECJ
Formula
C27H38N2O4
Canonical SMILES
CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
InChI
InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
InChIKey
SGTNSNPWRIOYBX-UHFFFAOYSA-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
D-702 DM015209
157039
Unclear - Unclear 1 [8]
Norverapamil DM005256
104972
Unclear - Unclear 1 [8]
O-Desmethylverapamil (D-703) DM005259
625729
Unclear - Unclear 1 [8]
Verapamil metabolite D-617 DM005252
93168
Unclear - Unclear 1 [8]
D-715 (PR-22) DM018495 N. A. Unclear - Unclear 2 [8]
Verapamil metabolite D-620 DM005254
161569
Unclear - Unclear 2 [8]
Verapamil metabolite PR-25 DM005253
10016311
Unclear - Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010523 Verapamil Norverapamil Unclear - Unclear CYP2C8 ... [8]
MR010526 Verapamil D-617 Unclear - Unclear CYP2C8 [8]
MR010529 Verapamil D-702 Unclear - Unclear CYP2C8 ... [8]
MR010531 Verapamil N19 (D-703) Unclear - Unclear CYP2C8 ... [8]
MR010527 D-617 PR 25 Unclear - Unclear Unclear [8]
MR010528 D-617 D-620 Unclear - Unclear CYP3A4 ... [8]
MR010530 D-702 D-620 Unclear - Unclear CYP3A4 ... [8]
MR010524 Norverapamil D-715 (PR-22) Unclear - Unclear CYP2C8 [8]
MR010525 Norverapamil D-620 Unclear - Unclear CYP2C8 [8]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4] , [5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4] , [6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 8  DME(s)
References
1 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 071881.
2 ClinicalTrials.gov (NCT04351763) Amiodarone or Verapamil in COVID-19 Hospitalized Patients With Symptoms. U.S. National Institutes of Health.
3 DrugBank(Pharmacology-Metabolism):Verapamil
4 Lactobacillus rhamnosus induces CYP3A and changes the pharmacokinetics of verapamil in rats
5 A Mechanistic, Enantioselective, Physiologically Based Pharmacokinetic Model of Verapamil and Norverapamil, Built and Evaluated for Drug-Drug Interaction Studies
6 Effect of verapamil on the pharmacokinetics of hydroxycamptothecin and its potential mechanism
7 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
8 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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