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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:05 UTC
HMDB IDHMDB0015163
Secondary Accession Numbers
  • HMDB15163
Metabolite Identification
Common NameIrbesartan
DescriptionIrbesartan, also known as avapro or BMS 186295, belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. The use of ARBs is pending revision due to findings from several clinical trials suggesting that this class of drugs may be associated with a small increased risk of cancer. The majority of metabolism occurs through the action of CYP2C9 with a negligible contribution from CYP3A4. Irbesartan is a strong basic compound (based on its pKa). In humans, irbesartan is involved in irbesartan action pathway. Some hydroxylation also occurs in irbesartan metabolism. Irbesartan and its active metabolite bind the AT1 receptor with 8500 times more affinity than they bind to the AT2 receptor. Irbesartan is an angiotensin receptor blocker (ARB) used mainly for the treatment of hypertension.
Structure
Data?1582753265
Synonyms
ValueSource
2-Butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-oneChEBI
AvaproChEBI
BMS 186295ChEBI
AprovelHMDB
2-N-Butyl-3-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4,4)non-1-en-4-oneHMDB
KarveaHMDB
Chemical FormulaC25H28N6O
Average Molecular Weight428.5294
Monoisotopic Molecular Weight428.232459548
IUPAC Name2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one
Traditional Nameirbesartan
CAS Registry Number138402-11-6
SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
InChI Identifier
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)
InChI KeyYOSHYTLCDANDAN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Phenyltetrazole
  • Alpha-amino acid or derivatives
  • Imidazolinone
  • Azole
  • 2-imidazoline
  • Heteroaromatic compound
  • Tetrazole
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0088 g/LNot Available
LogP6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0088 g/LALOGPS
logP4.51ALOGPS
logP5.5ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.72 m³·mol⁻¹ChemAxon
Polarizability47.59 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003s-4369200000-becba9ffa9e272aa32e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056r-0361900000-10d459e7561fdaacc9d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0000900000-b6619e18dca63147588dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004l-0801900000-b884691a3577ffab749fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-130056acf88b6caed131Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-97919ed4377a869dc8ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-55cf0ae2c686af5c38e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0908000000-0c994ee86857e7d63e48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0000900000-b610a12a9852ff1a11c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900100000-c9024d0b00a0ec781fa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-cb54b7c0917d67313110Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-4e0d1ebbc0609ecaa59dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-ec0fc575bb22a99c258dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-f1f0658a24e5097674e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0000900000-12da76073bae1768b7e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-cce4e6a8c5bbaa66c902Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-c7202e4de31fc762cf2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-ad31324f1b1a0e9be0b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-2301c02c521c3dab9c79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-8b6e9e772c5af1365e87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0031900000-17809285e0a3b4dd1e06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003b-3498400000-cd1509ce49c60cd950e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9270000000-90cfedba054108dd4631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400900000-841b2c08c5c0ba645872Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1912600000-08a0ed3935f141804219Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-4900000000-9cee06a170bc51b2daf4Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01029 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01029 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01029
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3618
KEGG Compound IDC07469
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIrbesartan
METLIN IDNot Available
PubChem Compound3749
PDB IDNot Available
ChEBI ID5959
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. [PubMed:10822210 ]
  2. Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, Ritz E, Atkins RC, Rohde R, Raz I: Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes. N Engl J Med. 2001 Sep 20;345(12):851-60. [PubMed:11565517 ]
  3. Croom KF, Curran MP, Goa KL, Perry CM: Irbesartan: a review of its use in hypertension and in the management of diabetic nephropathy. Drugs. 2004;64(9):999-1028. [PubMed:15101793 ]