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Irbesartan

July 24, 2017
Common Name

Irbesartan Description

Irbesartan 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 AprovelMeSH 2-N-Butyl-3-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4,4)non-1-en-4-oneMeSH KarveaMeSH

Chemical Formlia

C25H28N6O Average Molecliar Weight

428.5294 Monoisotopic Molecliar Weight

428.232459548 IUPAC Name

2-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 Name

irbesartan CAS Registry Number

138402-11-6 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 Key

YOSHYTLCDANDAN-UHFFFAOYSA-N Chemical Taxonomy Description

This compound 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. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Biphenyls and derivatives Direct Parent

Biphenyls and derivatives Alternative Parents

  • Phenyltetrazoles and derivatives
  • Alpha amino acids and derivatives
  • Imidazolinones
  • Heteroaromatic compounds
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboximidamides
  • Carboxamidines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • azaspiro compound (CHEBI:5959 )
  • biphenylyltetrazole (CHEBI:5959 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Angiotensin II Receptor Antagonists
  • Angiotensin II Type 1 Receptor Blockers
  • Antihypertensive Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point180 – 181 °CNot Available Boiling PointNot AvailableNot Available Water Solubility8.84e-03 g/LNot Available LogP6Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0088 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity136.72 m3·mol-1ChemAxon Polarizability47.59 Å3ChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-004i-0000900000-b6619e18dca63147588dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-004l-0801900000-b884691a3577ffab749fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0006-0900000000-130056acf88b6caed131View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0006-0900000000-97919ed4377a869dc8ccView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0006-0900000000-55cf0ae2c686af5c38e3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0007-0908000000-0c994ee86857e7d63e48View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004i-0000900000-b610a12a9852ff1a11c1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900100000-c9024d0b00a0ec781fa2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-cb54b7c0917d67313110View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-4e0d1ebbc0609ecaa59dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-ec0fc575bb22a99c258dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00di-0900000000-f1f0658a24e5097674e0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004i-0000900000-12da76073bae1768b7e2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-cce4e6a8c5bbaa66c902View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-c7202e4de31fc762cf2dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-ad31324f1b1a0e9be0b8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0900000000-2301c02c521c3dab9c79View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00di-0900000000-8b6e9e772c5af1365e87View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0007-0908000000-97706153fba817a654e4View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Irbesartan Action PathwaySMP00161Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01029

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01029

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01029 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    3618 KEGG Compound ID

    C07469 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Irbesartan NuGOwiki Link

    HMDB15163 Metagene Link

    HMDB15163 METLIN ID

    Not Available PubChem Compound

    3749 PDB ID

    Not Available ChEBI ID

    5959

    Product: Z-VAD-FMK

    References Synthesis Reference Not 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 ]

    PMID: 21177701

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