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

General Information of Drug (ID: DR0264)
Drug Name
Candesartan cilexetil
Prodrug Info Candesartan cilexetil is the prodrug of Candesartan
Synonyms
Candesartan; Candesartan (Cilexetil); Candesartan cilexetil; Candesartan cilexetil [USAN]; Kenzen; MFCD00871371; Parapres; TCV 116; TCV-116; TCY 116; Candesartancilexetil; Blopress; C24H20N6O3; CHEBI:3347; CHEMBL1016; CV 11974; CV-11974; NCGC00167474-01; Ratacand; S8Q36MD2XX; UNII-S8Q36MD2XX; 1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid; 139481-59-7; 2-Ethoxy-1-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic acid; 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]-3h-benzoimidazole-4-carboxylic acid; 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid; AK-57139; 145040-37-5; 1H-Benzimidazolium, 7-carboxy-1-(2-((cyclohexylcarbonyl)oxy)ethyl)-2-ethoxy-1-(2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)-, hydroxide, inner salt, (+-)-; AK-75900; Amias; Atacand; C33H34N6O6; CANDESARTAN CILEXTIL; CHEBI:3348; CHEMBL1014
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 610.7 Topological Polar Surface Area 143
Heavy Atom Count 45 Rotatable Bond Count 13
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
2540
ChEBI ID
CHEBI:3348
CAS Number
145040-37-5
TTD Drug ID
D0D5SQ
Formula
C33H34N6O6
Canonical SMILES
CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6
InChI
1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
InChIKey
GHOSNRCGJFBJIB-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
Candesartan DM000538
2541
Hydrolysis - Hydrolysis 1 [2]
Candesartan N2-glucuronide DM000540
46780161
Conjugation - N-Glucuronidation 2 [5]
Candesartan O-glucuronide DM000539
131769984
Conjugation - O-Glucuronidation 2 [5]
O-Deethylated candesartan DM000541
10047287
Oxidation - O-Deethylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000554 Candesartan cilexetil Candesartan Hydrolysis - Hydrolysis CES1 [2]
MR000551 Candesartan Candesartan O-glucuronide Conjugation - O-Glucuronidation PTGS1 [5]
MR000552 Candesartan Candesartan N2-glucuronide Conjugation - N-Glucuronidation UGT1A1 ... [5]
MR000553 Candesartan O-Deethylated candesartan Oxidation - O-Deethylation CYP2C9 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 8  DME(s)
References
1 Candesartan Cilexetil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Different hydrolases involved in bioactivation of prodrug-type angiotensin receptor blockers: carboxymethylenebutenolidase and carboxylesterase 1. Drug Metab Dispos. 2013 Nov;41(11):1888-95.
3 Product Monograph of Atacand.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan. Biochem Pharmacol. 2008 Sep 15;76(6):763-72.
6 The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan Biochem Pharmacol. 2008 Sep 15;76(6):763-72. doi: 10.1016/j.bcp.2008.07.006.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.