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

General Information of Drug (ID: DR1165)
Drug Name
Nisoldipine
Synonyms
Nisocor; Nisoldipin; Nisoldipino; Nisoldipino [INN-Spanish]; Nisoldipinum; Nisoldipinum [INN-Latin]; Syscor; VKQFCGNPDRICFG-UHFFFAOYSA-N; Baymycard; Zadipina; nisoldipine; 3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; 63675-72-9; BRN 0454188; Bay k 5552; Bay-k-5552; C20H24N2O6; CHEBI:76917; CHEMBL441428; EINECS 264-407-7; MFCD00478055; Sular; methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 388.4 Topological Polar Surface Area 110
Heavy Atom Count 28 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
4499
PubChem SID
9901 ; 5054384 ; 6595685 ; 6951250 ; 7594280 ; 7847684 ; 7980129 ; 8152772 ; 11528722 ; 12012773 ; 14780577 ; 26719878 ; 26758055 ; 29223593 ; 46386699 ; 46504546 ; 48416330 ; 49681768 ; 53787999 ; 56313694 ; 56463094 ; 57322301 ; 80626920 ; 81092916 ; 92307945 ; 92308528 ; 92308896 ; 92711446 ; 93166842 ; 103219831 ; 103680984 ; 104306583 ; 117875317 ; 118048486 ; 121363368 ; 124658895 ; 124799896 ; 125355226 ; 126630843 ; 126657331 ; 126665640 ; 131322121 ; 131846259 ; 134337886 ; 135004762 ; 135650722 ; 135692260 ; 137122027 ; 137349418 ; 139157574
ChEBI ID
CHEBI:76917
CAS Number
63675-72-9
TTD Drug ID
D0S5CU
Formula
C20H24N2O6
Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OCC(C)C)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
InChI
1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
InChIKey
VKQFCGNPDRICFG-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 [4]
Nisoldipine metabolite M13 DM002256
10385461
Oxidation - Dehydrogenation 1 [4]
Nisoldipine metabolite M9 DM002251
184690
Unclear 1 [4]
Furnidipine M-2 DM002257
175469
Oxidation - Dehydrogenation 2 [4]
Furnidipine M-2 DM002257
175469
Unclear 2 [5]
Nisoldipine metabolite M10 DM002252
91668155
Unclear 2 [4]
Nisoldipine metabolite M10 DM002252
91668155
Oxidation - Dehydrogenation 2 [6]
Nisoldipine metabolite M4 DM002253
9977556
Unclear 3 [4]
Nisoldipine metabolite M4 DM002253
9977556
Oxidation - Chain Hydroxylation 3 [4]
Nisoldipine metabolite M5 DM002254
91668156
Unclear 4 [4]
Nisoldipine metabolite M5 DM002254
91668156
Oxidation - Chain Hydroxylation 4 [4]
Nisoldipine metabolite M12 DM002255 N. A. Conjugation - Glucuronidation 5 [4]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001759 Nisoldipine Nisoldipine metabolite M9 Unclear Unclear [4]
MR001760 Nisoldipine Nisoldipine metabolite M13 Oxidation - Dehydrogenation CYP3A4 [4]
MR001761 Nisoldipine Nisoldipine metabolite M1 Unclear Unclear [4]
MR001758 Nisoldipine metabolite M1 Nisoldipine metabolite M2 Oxidation - Dehydrogenation CYP3A4 [4]
MR001756 Nisoldipine metabolite M13 Nisoldipine metabolite M10 Unclear Unclear [4]
MR001757 Nisoldipine metabolite M13 Nisoldipine metabolite M2 Unclear Unclear [5]
MR001752 Nisoldipine metabolite M9 Nisoldipine metabolite M10 Oxidation - Dehydrogenation CYP3A4 [6]
MR001753 Nisoldipine metabolite M10 Nisoldipine metabolite M4 Oxidation - Chain Hydroxylation Unclear [4]
MR001754 Nisoldipine metabolite M4 Nisoldipine metabolite M5 Oxidation - Chain Hydroxylation Unclear [4]
MR001755 Nisoldipine metabolite M5 Nisoldipine metabolite M12 Conjugation - Glucuronidation Unclear [4]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Nisoldipine 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 Drug Interactions Flockhart Table
4 Clinical pharmacokinetics of nisoldipine coat-core Clin Pharmacokinet. 1998 Sep;35(3):191-208. doi: 10.2165/00003088-199835030-00003.
5 Pharmacokinetics and metabolism of nilutamide Urology. 1991;37(2 Suppl):13-9. doi: 10.1016/0090-4295(91)80096-p.
6 U. S. FDA Label -Nisoldipine

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