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

General Information of Drug (ID: DR0098)
Drug Name
Amlodipine besylate
Synonyms
Amcard; Amdepin; Amdipin; Amlodin; Amlodipine; Amlodipine (besylate); Amlodipine benzenesulfonate; Amlodipine besylate (Norvasc); Amlodipine besylate [USAN]; Amlogard; Amlopin; Amlosyn; Antacal; Astudar; CHEBI:2669; Cardiorex; Cordarene; HSDB 7079; Monopina; Myodura; NCGC00095835-01; Norlopin; Norvas; Norvask; Pelmec; Tensivask; Terloc; UK 48340-26; Amlocard; Amlodipine Free Base; Amlodipine [INN:BAN]; Amlodipino; Amlodipino [Spanish]; Amlodipinum; Amlodipinum [Latin]; Amlodis; Amlor; CHEBI:2668; Caduet; Coroval; HTIQEAQVCYTUBX-UHFFFAOYSA-N; Lipinox; Norvasc; UK-4834011; amlodipine; (s)-(-)-amlodipine; 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; 88150-42-9; AMLODIPINE BASE; 111470-99-6; 3-ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate benzenesulfonate; AMLODIPINE BESYLATE
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 567.1 Topological Polar Surface Area 163
Heavy Atom Count 38 Rotatable Bond Count 11
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
60496
PubChem SID
7847681 ; 8186890 ; 11363467 ; 11366029 ; 11368591 ; 11376753 ; 11494387 ; 11528718 ; 14837689 ; 24890999 ; 26612823 ; 26681028 ; 26749852 ; 43117888 ; 49830358 ; 56320988 ; 56423826 ; 57314022 ; 74532315 ; 85174483 ; 87246412 ; 88802066 ; 92308178 ; 92711324 ; 103770385 ; 104320906 ; 105807462 ; 117633239 ; 118048672 ; 118843684 ; 119526885 ; 124637367 ; 124757512 ; 124800074 ; 124801083 ; 125164316 ; 125307717 ; 125337849 ; 126630976 ; 126657421 ; 126665382 ; 129990383 ; 131294547 ; 135016978 ; 135692287 ; 135698252 ; 137241534 ; 144075783 ; 144115369 ; 144205078
ChEBI ID
CHEBI:2669
CAS Number
111470-99-6
TTD Drug ID
D0H7WA
Formula
C26H31ClN2O8S
Canonical SMILES
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN.C1=CC=C(C=C1)S(=O)(=O)O
InChI
1S/C20H25ClN2O5.C6H6O3S/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;7-10(8,9)6-4-2-1-3-5-6/h5-8,17,23H,4,9-11,22H2,1-3H3;1-5H,(H,7,8,9)
InChIKey
ZPBWCRDSRKPIDG-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
Amlodipine besylate metabolite M3 DM001338 N. A. Oxidation - Monohydroxylation 1 [3]
Amlodipine besylate metabolite M5 DM001339 N. A. Oxidation - Monohydroxylation 1 [3]
Amlodipine besylate metabolite M6 DM001340 N. A. Oxidation - O-Demethylation 1 [3]
Amlodipine besylate metabolite M8 DM001341 N. A. Oxidation - Monohydroxylation 1 [3]
Amlodipine besylate metabolite M9 DM001328 N. A. Oxidation - Dehydrogenation 1 [3]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 2 [5]
Amlodipine besylate metabolite M1 DM001334 N. A. Oxidation - O-Demethylation 2 [3]
Amlodipine besylate metabolite M10 DM001329 N. A. Oxidation - Oxidative Deamination 2 [3]
Amlodipine besylate metabolite M4 DM001335 N. A. Oxidation - O-Dealkylation 2 [3]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 3 [5]
Amlodipine besylate metabolite M12 DM001333 N. A. Unclear 3 [3]
Amlodipine besylate metabolite H DM001330 N. A. Unclear 4 [5]
⏷ 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
MR000181 Amlodipine besylate Amlodipine besylate metabolite M9 Oxidation - Dehydrogenation CYP3A4 [3]
MR000182 Amlodipine besylate Amlodipine besylate metabolite M3 Oxidation - Monohydroxylation Unclear [3]
MR000183 Amlodipine besylate Amlodipine besylate metabolite M5 Oxidation - Monohydroxylation Unclear [3]
MR000184 Amlodipine besylate Amlodipine besylate metabolite M6 Oxidation - O-Demethylation Unclear [3]
MR000185 Amlodipine besylate Amlodipine besylate metabolite M8 Oxidation - Monohydroxylation Unclear [3]
MR000173 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M10 Oxidation - Oxidative Deamination Unclear [3]
MR000174 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M1 Oxidation - O-Demethylation Unclear [3]
MR000175 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite M4 Oxidation - O-Dealkylation Unclear [3]
MR000176 Amlodipine besylate metabolite M9 Amlodipine besylate metabolite H Unclear Unclear [5]
MR000180 Amlodipine besylate metabolite M1 Amlodipine besylate metabolite H Unclear Unclear [5]
MR000177 Amlodipine besylate metabolite M10 Amlodipine besylate metabolite H Unclear Unclear [5]
MR000178 Amlodipine besylate metabolite M10 Amlodipine besylate metabolite M12 Unclear Unclear [3]
MR000179 Amlodipine besylate metabolite H Amlodipine besylate metabolite H Unclear Unclear [5]
⏷ 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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
References
1 Amlodipine Besylate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Conformational adaptation of human cytochrome P450 2B6 and rabbit cytochrome P450 2B4 revealed upon binding multiple amlodipine molecules. Biochemistry. 2012 Sep 18;51(37):7225-38.
3 Amlodipine metabolism in human liver microsomes and roles of CYP3A4/5 in the dihydropyridine dehydrogenation. Drug Metab Dispos. 2014 Feb;42(2):245-9.
4 Construction and verification of CYP3A5 gene polymorphisms using a Saccharomyces cerevisiae expression system to predict drug metabolism. Mol Med Rep. 2017 Apr;15(4):1593-1600.
5 Metabolism and kinetics of amlodipine in man Xenobiotica. 1988 Feb;18(2):245-54. doi: 10.3109/00498258809041660.

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