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

General Information of Drug (ID: DR0879)
Drug Name
Irbesartan
Synonyms
Irbesartan [USAN:INN]; J0E2756Z7N; Karvea; SR 47436; SR-47436; YOSHYTLCDANDAN-UHFFFAOYSA-N; irbesartan; 138402-11-6; Aprovel; Avapro; 2-butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one; 3-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one; 8-butyl-7-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-7,9-diazaspiro[4.4]non-8-en-6-one; AK-57149; BMS 186295; BMS-186295; C25H28N6O; CHEBI:5959; CHEMBL1513; MFCD00864464; NCGC00095122-01; UNII-J0E2756Z7N
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 428.5 Topological Polar Surface Area 87.1
Heavy Atom Count 32 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3749
PubChem SID
9672 ; 5243560 ; 7847589 ; 8152372 ; 11364645 ; 11367207 ; 11369769 ; 11372006 ; 11374741 ; 11377931 ; 11485625 ; 11489491 ; 11490809 ; 11492936 ; 11495565 ; 11528645 ; 12014641 ; 14758693 ; 14905264 ; 26612692 ; 26680708 ; 26719813 ; 26748950 ; 26748951 ; 29222869 ; 46386566 ; 46506575 ; 46530573 ; 47365300 ; 48035232 ; 48416128 ; 49681744 ; 49830881 ; 50107493 ; 53787775 ; 56312044 ; 56313979 ; 57321974 ; 77118987 ; 81092816 ; 85174437 ; 85209120 ; 85789259 ; 91011661 ; 92124749 ; 92307926 ; 92308458 ; 92713301 ; 93166505 ; 93621098
ChEBI ID
ChEBI:5959
CAS Number
138402-11-6
TTD Drug ID
D00JAU
Formula
C25H28N6O
Canonical SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5
InChI
1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)
InChIKey
YOSHYTLCDANDAN-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
Irbesartan derivative M3 DM000997
11676932
Oxidation - Oxidation 1 [7] , [5]
Irbesartan derivative M4 DM000988
154700101
Oxidation - Hydroxylation 1 [7] , [5]
Irbesartan derivative M5 DM000992
101944494
Oxidation - Hydroxylation 1 [7] , [5]
Irbesartan derivative M7 DM000993 N. A. Oxidation - Hydroxylation 1 [7] , [5]
Irbesartan derivative M8 DM000998 N. A. Conjugation - N-Glucuronidation 1 [7] , [5]
Irbesartan metabolite F DM000999
10176511
Oxidation - N-Dealkylation 1 [8]
Irbesartan-TP335 DM000994
143603582
Oxidation - Hydrolysis; N-Demethylation 1 [7] , [5]
SR 49498 DM000996
68617604
Hydrolysis - Hydrolysis 1 [7] , [5]
Irbesartan derivative M1 DM000991
101944491
Oxidation - Hydroxylation 2 [5]
Irbesartan derivative M6 DM000989
91800165
Oxidation - Oxidation 2 [5]
Irbesartan-TP267 DM000995
19388302
Oxidation - N-Demethylation; Oxidation 2 [5]
Irbesartan derivative M2 DM000990
101944492
Oxidation - Oxidation 3 [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
MR001215 Irbesartan Irbesartan derivative M4 Oxidation - Hydroxylation CYP2C9 [7], [5]
MR001216 Irbesartan Irbesartan derivative M5 Oxidation - Hydroxylation CYP2C9 [7], [5]
MR001217 Irbesartan Irbesartan derivative M7 Oxidation - Hydroxylation CYP2C9 [7], [5]
MR001218 Irbesartan Irbesartan-TP335 Oxidation - Hydrolysis; N-Demethylation Unclear [7], [5]
MR001219 Irbesartan SR 49498 Hydrolysis - Hydrolysis PTGS1 [7], [5]
MR001220 Irbesartan Irbesartan derivative M3 Oxidation - Oxidation Unclear [7], [5]
MR001221 Irbesartan Irbesartan derivative M8 Conjugation - N-Glucuronidation UGT1A3 [7], [5]
MR001222 Irbesartan Irbesartan metabolite F Oxidation - N-Dealkylation Unclear [8]
MR001208 Irbesartan derivative M4 Irbesartan derivative M6 Oxidation - Oxidation Unclear [5]
MR001209 Irbesartan derivative M4 Irbesartan derivative M1 Oxidation - Hydroxylation Unclear [5]
MR001212 Irbesartan derivative M5 Irbesartan derivative M1 Oxidation - Hydroxylation CYP2C9 [5]
MR001213 Irbesartan derivative M7 Irbesartan derivative M1 Oxidation - Hydroxylation CYP2C9 [5]
MR001214 Irbesartan-TP335 Irbesartan-TP267 Oxidation - N-Demethylation; Oxidation Unclear [5]
MR001211 Irbesartan derivative M1 Irbesartan derivative M2 Oxidation - Oxidation Unclear [5]
MR001210 Irbesartan derivative M6 Irbesartan derivative M2 Oxidation - Oxidation Unclear [5]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[5]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [6]
⏷ Show the Full List of 16  DME(s)
References
1 Irbesartan was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78.
3 Rapid detection of the known SNPs of CYP2C9 using oligonucleotide microarray. World J Gastroenterol. 2003 Jun;9(6):1342-6.
4 Drug interactions with irbesartan. Clin Pharmacokinet. 2001;40(8):605-14.
5 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.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Biotransformation of irbesartan in man Drug Metab Dispos. 1998 May;26(5):408-17.
8 Disposition of irbesartan, an angiotensin II AT1-receptor antagonist, in mice, rats, rabbits, and macaques Drug Metab Dispos. 2000 Jan;28(1):79-88.

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