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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015163
Secondary Accession Numbers
  • HMDB15163
Metabolite Identification
Common NameIrbesartan
DescriptionIrbesartan is an angiotensin receptor blocker (ARB) used mainly for the treatment of hypertension. It competes with angiotensin II for binding at the AT1 receptor subtype. Unlike ACE inhibitors, ARBs do not have the adverse effect of dry cough. 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.
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0088 g/LNot Available
LogP6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM200.830932474
[M+H]+Not Available201.235http://allccs.zhulab.cn/database/detail?ID=AllCCS00000842
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.67331661259
DarkChem[M-H]-201.0431661259
DeepCCS[M+H]+198.06830932474
DeepCCS[M-H]-195.7130932474
DeepCCS[M-2H]-229.37430932474
DeepCCS[M+Na]+204.84430932474
AllCCS[M+H]+205.632859911
AllCCS[M+H-H2O]+203.432859911
AllCCS[M+NH4]+207.632859911
AllCCS[M+Na]+208.232859911
AllCCS[M-H]-201.332859911
AllCCS[M+Na-2H]-201.932859911
AllCCS[M+HCOO]-202.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IrbesartanCCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N14415.8Standard polar33892256
IrbesartanCCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N13922.0Standard non polar33892256
IrbesartanCCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N13923.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Irbesartan,1TMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C13905.7Semi standard non polar33892256
Irbesartan,1TMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C13803.0Standard non polar33892256
Irbesartan,1TMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C15262.8Standard polar33892256
Irbesartan,1TBDMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14032.6Semi standard non polar33892256
Irbesartan,1TBDMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14038.6Standard non polar33892256
Irbesartan,1TBDMS,isomer #1CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C15282.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Irbesartan GC-MS (Non-derivatized) - 70eV, Positivesplash10-003s-4369200000-becba9ffa9e272aa32e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Irbesartan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-qTof , Positive-QTOFsplash10-056r-0361900000-10d459e7561fdaacc9d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-QTOF , negative-QTOFsplash10-004i-0000900000-b6619e18dca63147588d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-QTOF , negative-QTOFsplash10-004l-0801900000-b884691a3577ffab749f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-130056acf88b6caed1312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-97919ed4377a869dc8cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-55cf0ae2c686af5c38e32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0007-0908000000-0c994ee86857e7d63e482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0000900000-b610a12a9852ff1a11c12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900100000-c9024d0b00a0ec781fa22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-cb54b7c0917d673131102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-4e0d1ebbc0609ecaa59d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-ec0fc575bb22a99c258d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-00di-0900000000-f1f0658a24e5097674e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-004i-0000900000-12da76073bae1768b7e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-cce4e6a8c5bbaa66c9022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-c7202e4de31fc762cf2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-ad31324f1b1a0e9be0b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-2301c02c521c3dab9c792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Irbesartan LC-ESI-ITFT , negative-QTOFsplash10-00di-0900000000-8b6e9e772c5af1365e872017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 10V, Positive-QTOFsplash10-004i-0031900000-17809285e0a3b4dd1e062016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 20V, Positive-QTOFsplash10-003b-3498400000-cd1509ce49c60cd950e12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 40V, Positive-QTOFsplash10-001r-9270000000-90cfedba054108dd46312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 10V, Negative-QTOFsplash10-004i-0400900000-841b2c08c5c0ba6458722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 20V, Negative-QTOFsplash10-002f-1912600000-08a0ed3935f1418042192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irbesartan 40V, Negative-QTOFsplash10-000x-4900000000-9cee06a170bc51b2daf42016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01029 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents 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. 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 ]
  3. 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 ]