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

General Information of Drug (ID: DR1152)
Drug Name
Nifedipine
Synonyms
Nifangin; Nifecard; Nifediac; Nifedical; Nifedicor; Nifedin; Nifedipino; Nifedipinum; Nifelat; Oxcord; Pidilat; Procardia; Procardia XL; Adalat; Adalat CC; Adalat LA; Adalate; Adapine; Afeditab CR; Anifed; Chronadalate; Citilat; Coracten; Cordafen; Cordicant; Cordipin; Corinfar; Corotrend; Dignokonstant; Ecodipi; Ecodipin; Fenamon; Fenihidin; Fenihidine; Hexadilat; Introcar; Kordafen; Macorel; Megalat; Sepamit; Tibricol; Zenusin; nifedipine; 21829-25-4; Bay-a-1040; Orix; dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Indication Angina pectoris [ICD11: BA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 346.3 Topological Polar Surface Area 110
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
4485
PubChem SID
9475 ; 634276 ; 841058 ; 855613 ; 3153213 ; 5010834 ; 6300547 ; 7847503 ; 7980124 ; 8145946 ; 8149443 ; 8152762 ; 10321407 ; 10513802 ; 11111548 ; 11111549 ; 11113899 ; 11119993 ; 11120481 ; 11120969 ; 11121456 ; 11121936 ; 11147076 ; 11335488 ; 11360727 ; 11362525 ; 11363873 ; 11364812 ; 11365087 ; 11366435 ; 11367374 ; 11367649 ; 11368997 ; 11369936 ; 11370321 ; 11370322 ; 11371671 ; 11372976 ; 11373250 ; 11373766 ; 11375536 ; 11375811 ; 11377159 ; 11378103 ; 11461699 ; 11466091 ; 11467211 ; 11484752 ; 11485902 ; 11488874
ChEBI ID
ChEBI:7565
CAS Number
21829-25-4
TTD Drug ID
D04OSE
Formula
C17H18N2O6
Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
InChI
1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
InChIKey
HYIMSNHJOBLJNT-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
2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid DM002192
10664296
Unclear 1 [8]
Dehydronifedipine DM002194
128753
Oxidation - Dehydrogenation 1 [9] , [8]
2-hydroxymethyl-pyridine carboxylic acid DM002193
21327179
Unclear 2 [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001737 Nifedipine 2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid Unclear CYP3A4 ... [8]
MR001738 Nifedipine Dehydronifedipine Oxidation - Dehydrogenation CYP3A4 [9], [8]
MR001736 2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid 2-hydroxymethyl-pyridine carboxylic acid Unclear CYP3A4 ... [10]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
References
1 Nifedipine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem. 2007 Mar;12(3):313-23.
3 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
4 Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52.
5 Molecular basis of polymorphic drug metabolism. J Mol Med (Berl). 1995 Nov;73(11):539-53.
6 Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. Br J Clin Pharmacol. 1997 Nov;44(5):505-11.
7 In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44.
8 Pharmacokinetics and metabolism of nifedipine Hypertension. 1983 Jul-Aug;5(4 Pt 2):II18-24. doi: 10.1161/01.hyp.5.4_pt_2.ii18.
9 The first pass metabolism of nifedipine in man Br J Clin Pharmacol. 1984 Dec;18(6):951-4. doi: 10.1111/j.1365-2125.1984.tb02569.x.
10 CYP3A5 genotype did not impact on nifedipine disposition in healthy volunteers Pharmacogenomics J. 2004;4(1):34-9. doi: 10.1038/sj.tpj.6500218.

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