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

General Information of Drug (ID: DR1668)
Drug Name
Valsartan
Synonyms
Diovan; Exforge; Kalpress; L-Valsartan; Provas; valsartan; (2S)-3-methyl-2-[pentanoyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid; (S)-2-(N-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid; 137862-53-4; 137863-60-6; 80M03YXJ7I; C24H29N5O3; CGP 48933; CGP-48933; CHEBI:9927; CHEMBL1069; MFCD00865840; Miten; N-(1-oxopentyl)-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine; N-(p-(o-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valine; Tareg; UNII-80M03YXJ7I
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 435.5 Topological Polar Surface Area 112
Heavy Atom Count 32 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
60846
PubChem SID
7847466 ; 11066615 ; 11364700 ; 11367262 ; 11369824 ; 11373100 ; 11374217 ; 11377988 ; 11484996 ; 11488936 ; 11491646 ; 11492564 ; 11495610 ; 14856825 ; 14881173 ; 26612829 ; 26719825 ; 43118184 ; 46386599 ; 46509000 ; 46530915 ; 47499543 ; 48393917 ; 49681716 ; 49830875 ; 50062253 ; 50467452 ; 53787275 ; 57314146 ; 81093312 ; 85788951 ; 90452226 ; 92124805 ; 92308052 ; 92308462 ; 92711441 ; 93166503 ; 99228303 ; 103292815 ; 103979540 ; 104253413 ; 104321799 ; 117541337 ; 117664453 ; 119526522 ; 123055291 ; 124659015 ; 124757534 ; 124800101 ; 125164338
ChEBI ID
ChEBI:9927
CAS Number
137862-53-4
TTD Drug ID
D06UDG
Formula
C24H29N5O3
Canonical SMILES
CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)C(C(C)C)C(=O)O
InChI
1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
InChIKey
ACWBQPMHZXGDFX-QFIPXVFZSA-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
Valeryl-4-hydroxyvalsartan DM002452
9911647
Oxidation - 4-Hydroxylation 1 [4] , [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002501 Valsartan Valeryl-4-hydroxyvalsartan Oxidation - 4-Hydroxylation CYP2C9 [4], [5], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [3]
⏷ Show the Full List of 11  DME(s)
References
1 Valsartan was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro inhibition screening of human hepatic P450 enzymes by five angiotensin-II receptor antagonists. Eur J Clin Pharmacol. 2000 May;56(2):135-40.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Optimization via experimental design of an SPE-HPLC-UV-fluorescence method for the determination of valsartan and its metabolite in human plasma samples J Sep Sci. 2006 Oct;29(15):2265-83. doi: 10.1002/jssc.200600093.
5 Effects of valsartan and valeryl 4-hydroxy valsartan on human platelets: a possible additional mechanism for clinical benefits J Cardiovasc Pharmacol. 2004 May;43(5):677-84. doi: 10.1097/00005344-200405000-00010.
6 Identification of cytochrome P450 forms involved in the 4-hydroxylation of valsartan, a potent and specific angiotensin II receptor antagonist, in human liver microsomes Xenobiotica. 2005 Jun;35(6):589-602. doi: 10.1080/00498250500158175.

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