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

General Information of Drug (ID: DR0099)
Drug Name
Amlodipine maleate
Synonyms
Amlodipine (maleate); Amlodipine maleate; Amlodipine maleate (USAN); Amlodipine maleate [USAN]; AmlodipineMaleate; C20H25ClN2O5.C4H4O4; UK 48,340-11; 3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (+-)-, (Z)-2-butenedioate (1:1); 3-Ethyl 5-methyl (+-)-2-((2-aminoethoxy)methyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate, maleate (1:1); 88150-47-4; Amlodipine (+-)-form maleate
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 524.9 Topological Polar Surface Area 175
Heavy Atom Count 36 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 11
Cross-matching ID
PubChem CID
6435922
CAS Number
88150-47-4
TTD Drug ID
D08JIV
Formula
C24H29ClN2O9
Canonical SMILES
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN.C(=CC(=O)O)C(=O)O
InChI
1S/C20H25ClN2O5.C4H4O4/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21;5-3(6)1-2-4(7)8/h5-8,17,23H,4,9-11,22H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
InChIKey
TZNOWAJJWCGILX-BTJKTKAUSA-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
Amlodipine besylate metabolite M3 DM001338 N. A. Oxidation - Monohydroxylation 1 [2]
Amlodipine besylate metabolite M5 DM001339 N. A. Oxidation - Monohydroxylation 1 [2]
Amlodipine besylate metabolite M6 DM001340 N. A. Oxidation - O-Demethylation 1 [2]
Amlodipine besylate metabolite M8 DM001341 N. A. Oxidation - Monohydroxylation 1 [2]
Amlodipine besylate metabolite M9 DM001328 N. A. Oxidation - Dehydrogenation 1 [2]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 2 [3]
Amlodipine besylate metabolite M1 DM001334 N. A. Oxidation - O-Demethylation 2 [2]
Amlodipine besylate metabolite M10 DM001329 N. A. Oxidation - Oxidative Deamination 2 [2]
Amlodipine besylate metabolite M4 DM001335 N. A. Oxidation - O-Dealkylation 2 [2]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 3 [3]
Amlodipine besylate metabolite M12 DM001333 N. A. Unclear 3 [2]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 4 [3]
⏷ 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
MR000194 Amlodipine besylate Amlodipine besylate metabolite M9 Oxidation - Dehydrogenation CYP3A4 [2]
MR000195 Amlodipine besylate Amlodipine besylate metabolite M3 Oxidation - Monohydroxylation Unclear [2]
MR000196 Amlodipine besylate Amlodipine besylate metabolite M5 Oxidation - Monohydroxylation Unclear [2]
MR000197 Amlodipine besylate Amlodipine besylate metabolite M6 Oxidation - O-Demethylation Unclear [2]
MR000198 Amlodipine besylate Amlodipine besylate metabolite M8 Oxidation - Monohydroxylation Unclear [2]
MR000186 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M10 Oxidation - Oxidative Deamination Unclear [2]
MR000187 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M1 Oxidation - O-Demethylation Unclear [2]
MR000188 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M4 Oxidation - O-Dealkylation Unclear [2]
MR000189 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite H Unclear Unclear [3]
MR000193 Amlodipine besylate metabolite M1 Amlodipine besylate metabolite H Unclear Unclear [3]
MR000190 Amlodipine besylate metabolite M10 Amlodipine besylate metabolite H Unclear Unclear [3]
MR000191 Amlodipine besylate metabolite M10 Amlodipine besylate metabolite M12 Unclear Unclear [2]
MR000192 Amlodipine besylate metabolite H Amlodipine besylate metabolite H Unclear Unclear [3]
⏷ Show the Full List of 13 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]
References
1 Amlodipine Maleate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Amlodipine metabolism in human liver microsomes and roles of CYP3A4/5 in the dihydropyridine dehydrogenation. Drug Metab Dispos. 2014 Feb;42(2):245-9.
3 Metabolism and kinetics of amlodipine in man Xenobiotica. 1988 Feb;18(2):245-54. doi: 10.3109/00498258809041660.

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