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

General Information of Drug (ID: DR1144)
Drug Name
Nicardipine hydrochloride
Synonyms
Nicardipine LA; Nicardipine [INN:BAN]; Nicardipino; Nicardipino [INN-Spanish]; Nicardipinum; Nicardipinum [INN-Latin]; Angioglebil; Bionicard; Cardene SR; Lincil; NICARDIPINE HYDROCHLORIDE; Nicardil; Nicardipine (Hydrochloride); Nicardipine HCl; Nicodel; Perdipina; Perdipine; RS-69216; RS-69216-XX-07-0; 2-(Benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylatemonohydrochloride; 54527-84-3; Dafil; Dagan; EINECS 259-198-4; Loxen; MFCD00057327; MLS000069782; Nicardipine hydrochloride [USAN:JAN]; SMR000058487; YC 93; YC-93; ZBBHBTPTTSWHBA-UHFFFAOYSA-N; nicardipine; 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-(benzylmethylamino)ethyl methyl ester; 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester; 55985-32-5; BRN 0504321; C26H29N3O6; CHEBI:7550; DSSTox_CID_3363; EINECS 259-932-3; NCGC00015747-03
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 516 Topological Polar Surface Area 114
Heavy Atom Count 36 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
41114
ChEBI ID
CHEBI:7551
CAS Number
54527-84-3
TTD Drug ID
D0T0KA
Formula
C26H30ClN3O6
Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC.Cl
InChI
1S/C26H29N3O6.ClH/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19;/h5-12,15,24,27H,13-14,16H2,1-4H3;1H
InChIKey
AIKVCUNQWYTVTO-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
De-benzylated nicardipine DM002174 N. A. Oxidation - N-Dealkylation 1 [4] , [2]
Dehydronicardipine DM002175
12529164
Oxidation - Heteroring Dehydrogenation 1 [4] , [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001729 Nicardipine hydrochloride De-benzylated nicardipine Oxidation - N-Dealkylation CYP2C8 ... [4], [2]
MR001730 Nicardipine hydrochloride Dehydronicardipine Oxidation - Heteroring Dehydrogenation CYP2C8 ... [4], [2], [3]
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 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
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Nicardipine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Inhibitory effects of nicardipine to cytochrome P450 (CYP) in human liver microsomes. Biol Pharm Bull. 2005 May;28(5):882-5.
4 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.

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