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

General Information of Drug (ID: DR1934)
Drug Name
Azilsartan medoxomil
Prodrug Info Azilsartan medoxomil is the prodrug of Azilsartan
Synonyms
Azilsartan (medoxomil); Azilsartan kamedoxomil; Edarbi; TAK-536; LL0G25K7I2; TAK 491; TAK-491; W-203965; azilsartan medoxomilo; azilsartanum medoxomilum; AZILSARTAN MEDOXOMIL; 1-[[2'-(2,5-Dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl]-2-ethoxy-1H-benziMidazole-7-carboxylic acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)Methyl ester; 863031-21-4; AK-68150; CHEBI:68845; UNII-LL0G25K7I2
Indication Essential hypertension [ICD11: BA00] Approved []
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 568.5 Topological Polar Surface Area 140
Heavy Atom Count 42 Rotatable Bond Count 10
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
135409642
ChEBI ID
CHEBI:68845
CAS Number
863031-21-4
TTD Drug ID
D02CDS
Formula
C30H24N4O8
Canonical SMILES
CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=O)OCC6=C(OC(=O)O6)C
InChI
1S/C30H24N4O8/c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
InChIKey
QJFSABGVXDWMIW-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
Azilsartan DM016621
135415867
Hydrolysis - Hydrolysis 1 [2]
Azilsartan M-I DM016451
101102054
Reduction - Decarboxylation 2 [2]
Azilsartan M-II DM016648
135742018
Oxidation - O-dealkylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013086 Azilsartan medoxomil Azilsartan Hydrolysis - Hydrolysis Unclear [2]
MR013087 Azilsartan Azilsartan M- Reduction - Decarboxylation CYP2C9 [2]
MR013088 Azilsartan Azilsartan M- Oxidation - O-dealkylation CYP2C8 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxymethylenebutenolidase (CMBL) DME0584 Homo sapiens
CMBL_HUMAN
3.1.1.45
[1]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
References
1 Different hydrolases involved in bioactivation of prodrug-type angiotensin receptor blockers: carboxymethylenebutenolidase and carboxylesterase 1. Drug Metab Dispos. 2013 Nov;41(11):1888-95.
2 Critical evaluation of the efficacy and tolerability of azilsartan

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