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

General Information of Drug (ID: DR0931)
Drug Name
Levamlodipine
Synonyms
Levamlodipine; Levoamlodipine; Levoamlodipine Besylate; Q-101935; S-Amlodipine; l-Amlodipine; (-)-(s)-Amlodipine; (4S)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester; (S)-Amlodipine; 0P6NLP6806; 103129-82-4; 3-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; CHEBI:53796; UNII-0P6NLP6806
Indication Essential hypertension [ICD11: BA00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 408.9 Topological Polar Surface Area 99.9
Heavy Atom Count 28 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
9822750
ChEBI ID
CHEBI:53796
CAS Number
103129-82-4
TTD Drug ID
D0I2WV
Formula
C20H25ClN2O5
Canonical SMILES
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
InChI
1S/C20H25ClN2O5/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/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1
InChIKey
HTIQEAQVCYTUBX-KRWDZBQOSA-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
Levamlodipine metabolite M6 DM002598
14271883
Unclear 1 [2] , [3]
Levamlodipine metabolite M9 DM002593
14271877
Oxidation - Dehydrogenation 1 [2] , [3]
Levamlodipine metabolite M1 DM002596
14271885
Unclear 2 [2] , [3]
Levamlodipine metabolite M10 DM002594 N. A. Oxidation - Oxidative Deamination 2 [2] , [3]
Levamlodipine metabolite M4 DM002597
14271893
Oxidation - O-Dealkylation 2 [2] , [3]
Levamlodipine metabolite M12 DM002595
14271878
Unclear 3 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001452 Levamlodipine Levamlodipine metabolite M9 Oxidation - Dehydrogenation CYP3A4 [2], [3]
MR001453 Levamlodipine Levamlodipine metabolite M6 Unclear Unclear [2], [3]
MR001448 Levamlodipine metabolite M9 Levamlodipine metabolite M10 Oxidation - Oxidative Deamination Unclear [2], [3]
MR001449 Levamlodipine metabolite M9 Levamlodipine metabolite M1 Unclear Unclear [2], [3]
MR001450 Levamlodipine metabolite M9 Levamlodipine metabolite M4 Oxidation - O-Dealkylation Unclear [2], [3]
MR001451 Levamlodipine metabolite M10 Levamlodipine metabolite M12 Unclear Unclear [2], [3]
⏷ Show the Full List of 6 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 ClinicalTrials.gov (NCT01131546) Efficacy and Safety of Levamlodipine Besylate Compared to Amlodipine Maleate in Patients With Essential Hypertension.
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 Absence of excretion of the active moiety of bisacodyl and sodium picosulfate into human breast milk: an open-label, parallel-group, multiple-dose study in healthy lactating women Drug Metab Pharmacokinet. 2011;26(5):458-64. doi: 10.2133/dmpk.dmpk-11-rg-007.

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