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Identification
NameIrbesartan
Accession NumberDB01029  (APRD00413)
TypeSmall Molecule
GroupsApproved, Investigational
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
Thumb
Synonyms
2-Butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one
Avapro
BMS 186295
Irbesartan
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Irbesartantablet300 mgoralActavis Pharma Company2011-03-21Not applicableCanada
Act Irbesartantablet150 mgoralActavis Pharma Company2011-03-21Not applicableCanada
Act Irbesartantablet75 mgoralActavis Pharma Company2011-03-21Not applicableCanada
Auro-irbesartantablet150 mgoralAuro Pharma Inc2013-07-08Not applicableCanada
Auro-irbesartantablet75 mgoralAuro Pharma Inc2013-07-08Not applicableCanada
Auro-irbesartantablet300 mgoralAuro Pharma Inc2013-07-08Not applicableCanada
Ava-irbesartantablet300 mgoralAvanstra Inc2011-11-232014-08-21Canada
Ava-irbesartantablet150 mgoralAvanstra Inc2011-11-232014-08-21Canada
Ava-irbesartantablet75 mgoralAvanstra Inc2011-11-232014-08-21Canada
Avaprotablet75 mgoralSanofi Aventis Canada Inc1998-06-22Not applicableCanada
Avaprotablet300 mgoralSanofi Aventis Canada Inc1998-07-22Not applicableCanada
Avaprotablet75 mg/1oralSanofi Aventis U.S. Llc2013-01-01Not applicableUs
Avaprotablet150 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-23Not applicableUs
Avaprotablet300 mg/1oralbryant ranch prepack1997-09-30Not applicableUs
Avaprotablet300 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-23Not applicableUs
Avaprotablet150 mg/1oralbryant ranch prepack1997-09-30Not applicableUs
Avaprotablet300 mg/1oralBristol Myers Squibb Company1997-09-302016-03-31Us
Avaprotablet150 mg/1oralCardinal Health1997-09-30Not applicableUs
Avaprotablet150 mg/1oralBristol Myers Squibb Company1997-09-302016-03-31Us
Avaprotablet300 mg/1oralPhysicians Total Care, Inc.2004-05-10Not applicableUs
Avaprotablet300 mg/1oralSanofi Aventis U.S. Llc2013-01-01Not applicableUs
Avaprotablet150 mg/1oralPhysicians Total Care, Inc.2000-11-21Not applicableUs
Avaprotablet150 mgoralSanofi Aventis Canada Inc1998-07-22Not applicableCanada
Avaprotablet150 mg/1oralSanofi Aventis U.S. Llc2013-01-01Not applicableUs
Avaprotablet150 mg/1oralLake Erie Medical DBA Quality Care Products LLC2013-01-01Not applicableUs
Bio-irbesartantablet300 mgoralBiomed PharmaNot applicableNot applicableCanada
Bio-irbesartantablet150 mgoralBiomed PharmaNot applicableNot applicableCanada
Bio-irbesartantablet75 mgoralBiomed PharmaNot applicableNot applicableCanada
Dom-irbesartantablet300 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-irbesartantablet75 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-irbesartantablet150 mgoralDominion Pharmacal2013-06-28Not applicableCanada
Ipg-irbesartantablet300 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-irbesartantablet150 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-irbesartantablet75 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Irbesartantablet300 mgoralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Irbesartantablet300 mgoralPro Doc Limitee2011-05-27Not applicableCanada
Irbesartantablet300 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Irbesartantablet150 mgoralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Irbesartantablet150 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Irbesartantablet150 mgoralPro Doc Limitee2011-05-27Not applicableCanada
Irbesartantablet75 mgoralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Irbesartantablet75 mgoralPro Doc Limitee2011-05-27Not applicableCanada
Irbesartantablet75 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Irbesartantablet300 mgoralSanis Health Inc2011-10-18Not applicableCanada
Irbesartantablet300 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Irbesartantablet300 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Irbesartantablet150 mgoralSanis Health Inc2011-10-18Not applicableCanada
Irbesartantablet150 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Irbesartantablet150 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Irbesartantablet75 mgoralSanis Health Inc2011-10-18Not applicableCanada
Irbesartantablet75 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Irbesartantablet75 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Jamp-irbesartantablet300 mgoralJamp Pharma Corporation2014-01-15Not applicableCanada
Jamp-irbesartantablet150 mgoralJamp Pharma Corporation2014-01-15Not applicableCanada
Jamp-irbesartantablet75 mgoralJamp Pharma Corporation2014-01-15Not applicableCanada
Mar-irbesartantablet75 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mar-irbesartantablet300 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mar-irbesartantablet150 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mint-irbesartantablet150 mgoralMint Pharmaceuticals Inc2015-01-14Not applicableCanada
Mint-irbesartantablet75 mgoralMint Pharmaceuticals Inc2015-01-14Not applicableCanada
Mint-irbesartantablet300 mgoralMint Pharmaceuticals Inc2015-01-14Not applicableCanada
Mylan-irbesartantablet300 mgoralMylan Pharmaceuticals Ulc2011-11-30Not applicableCanada
Mylan-irbesartantablet150 mgoralMylan Pharmaceuticals Ulc2011-11-30Not applicableCanada
Mylan-irbesartantablet75 mgoralMylan Pharmaceuticals Ulc2011-11-30Not applicableCanada
Ntp-irbesartantablet300 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-irbesartantablet150 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-irbesartantablet75 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Pendo-irbesartantablet300 mgoralPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
PMS-irbesartantablet300 mgoralPharmascience Inc2011-03-24Not applicableCanada
PMS-irbesartantablet150 mgoralPharmascience Inc2011-03-24Not applicableCanada
PMS-irbesartantablet75 mgoralPharmascience Inc2011-03-24Not applicableCanada
Priva-irbesartantablet150 mgoralPharmapar IncNot applicableNot applicableCanada
Priva-irbesartantablet300 mgoralPharmapar Inc2016-05-13Not applicableCanada
Priva-irbesartantablet75 mgoralPharmapar Inc2016-05-13Not applicableCanada
Q-irbesartantablet150 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-irbesartantablet75 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-irbesartantablet300 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Ran-irbesartantablet300 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-07-24Not applicableCanada
Ran-irbesartantablet150 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-07-24Not applicableCanada
Ran-irbesartantablet75 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-07-24Not applicableCanada
Ratio-irbesartantablet300 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Ratio-irbesartantablet150 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Ratio-irbesartantablet75 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Riva-irbesartantablet150 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Riva-irbesartantablet75 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Riva-irbesartantablet300 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Sandoz Irbesartantablet75 mgoralSandoz Canada Incorporated2011-03-21Not applicableCanada
Sandoz Irbesartantablet300 mgoralSandoz Canada Incorporated2011-03-21Not applicableCanada
Sandoz Irbesartantablet150 mgoralSandoz Canada Incorporated2011-03-21Not applicableCanada
Teva-irbesartantablet300 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Teva-irbesartantablet150 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Teva-irbesartantablet75 mgoralTeva Canada Limited2011-03-21Not applicableCanada
Van-irbesartantablet300 mgoralVanc Pharmaceuticals Inc2015-06-08Not applicableCanada
Van-irbesartantablet150 mgoralVanc Pharmaceuticals Inc2015-06-08Not applicableCanada
Van-irbesartantablet75 mgoralVanc Pharmaceuticals Inc2015-06-08Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-irbesartantablet300 mgoralApotex Inc2012-09-25Not applicableCanada
Apo-irbesartantablet150 mgoralApotex Inc2012-09-25Not applicableCanada
Apo-irbesartantablet75 mgoralApotex Inc2012-09-25Not applicableCanada
Irbesartantablet150 mg/1oralAv Pak2015-10-27Not applicableUs
Irbesartantablet150 mg/1oralAjanta Pharma Limited2015-01-20Not applicableUs
Irbesartantablet150 mg/1oralLegacy Pharmaceutical Packaging2012-03-30Not applicableUs
Irbesartantablet300 mg/1oralAurobindo Pharma Limited2012-09-27Not applicableUs
Irbesartantablet75 mg/1oralRoxane Laboratories, Inc.2012-10-15Not applicableUs
Irbesartantablet75 mg/1oralJubilant Cadista Pharmaceuticals Inc.2015-02-24Not applicableUs
Irbesartantablet150 mg/1oralAmerican Health Packaging2013-10-162015-12-29Us
Irbesartantablet150 mg/1oralUnichem Pharmaceuticals (USA), Inc.2016-04-01Not applicableUs
Irbesartantablet75 mg/1oralCamber Pharmaceuticals, Inc.2012-09-26Not applicableUs
Irbesartantablet, coated75 mg/1oralWatson Laboratories, Inc.2012-10-16Not applicableUs
Irbesartantablet300 mg/1oralbryant ranch prepack2012-09-27Not applicableUs
Irbesartantablet150 mg/150mgoralWestminster Pharmaceuticals, Llc2016-02-01Not applicableUs
Irbesartantablet75 mg/1oralSolco healthcare U.S., LLC2012-09-27Not applicableUs
Irbesartantablet75 mg/1oralAv Pak2015-10-27Not applicableUs
Irbesartantablet75 mg/1oralAjanta Pharma Limited2015-01-20Not applicableUs
Irbesartantablet300 mg/1oralLupin Pharmaceuticals, Inc.2012-10-23Not applicableUs
Irbesartantablet150 mg/1oralAurobindo Pharma Limited2012-09-27Not applicableUs
Irbesartantablet300 mg/1oralMacleods Pharmaceuticals Limited2012-09-27Not applicableUs
Irbesartantablet300 mg/1oralTeva Pharmaceuticals USA Inc2013-05-10Not applicableUs
Irbesartantablet, film coated300 mg/1oralApotex Corp.2012-10-16Not applicableUs
Irbesartantablet75 mg/75mgoralWestminster Pharmaceuticals, Llc2016-02-01Not applicableUs
Irbesartantablet300 mg/1oralScie Gen Pharmaceuticals, Inc.2015-12-07Not applicableUs
Irbesartantablet300 mg/1oralQualitest Pharmaceuticals2012-09-30Not applicableUs
Irbesartantablet150 mg/1oralLupin Pharmaceuticals, Inc.2012-10-23Not applicableUs
Irbesartantablet75 mg/1oralAurobindo Pharma Limited2012-09-27Not applicableUs
Irbesartantablet150 mg/1oralMacleods Pharmaceuticals Limited2012-09-27Not applicableUs
Irbesartantablet150 mg/1oralTeva Pharmaceuticals USA Inc2012-03-30Not applicableUs
Irbesartantablet, film coated150 mg/1oralApotex Corp.2012-10-16Not applicableUs
Irbesartantablet150 mg/1oralProficient Rx LP2012-03-30Not applicableUs
Irbesartantablet300 mg/1oralGolden State Medical Supply, Inc.2016-02-05Not applicableUs
Irbesartantablet150 mg/1oralScie Gen Pharmaceuticals, Inc.2015-12-07Not applicableUs
Irbesartantablet150 mg/1oralQualitest Pharmaceuticals2012-09-30Not applicableUs
Irbesartantablet75 mg/1oralLupin Pharmaceuticals, Inc.2012-10-23Not applicableUs
Irbesartantablet300 mg/1oralLUPIN LIMITED2012-10-23Not applicableUs
Irbesartantablet75 mg/1oralMacleods Pharmaceuticals Limited2012-09-27Not applicableUs
Irbesartantablet75 mg/1oralTeva Pharmaceuticals USA Inc2012-03-30Not applicableUs
Irbesartantablet, film coated75 mg/1oralApotex Corp.2012-10-16Not applicableUs
Irbesartantablet150 mg/1oralGolden State Medical Supply, Inc.2016-02-05Not applicableUs
Irbesartantablet75 mg/1oralQualitest Pharmaceuticals2012-09-30Not applicableUs
Irbesartantablet150 mg/1oralCarilion Materials Management2012-03-30Not applicableUs
Irbesartantablet150 mg/1oralLUPIN LIMITED2012-10-23Not applicableUs
Irbesartantablet75 mg/1oralScie Gen Pharmaceuticals, Inc.2015-12-07Not applicableUs
Irbesartantablet300 mg/1oralCamber Pharmaceuticals, Inc.2012-09-27Not applicableUs
Irbesartantablet300 mg/1oralRoxane Laboratories, Inc.2012-10-15Not applicableUs
Irbesartantablet300 mg/1oralJubilant Cadista Pharmaceuticals Inc.2015-02-24Not applicableUs
Irbesartantablet75 mg/1oralGolden State Medical Supply, Inc.2016-02-05Not applicableUs
Irbesartantablet, coated300 mg/1oralWatson Laboratories, Inc.2012-10-16Not applicableUs
Irbesartantablet150 mg/1oralAmerican Health Packaging2014-12-15Not applicableUs
Irbesartantablet75 mg/1oralLUPIN LIMITED2012-10-23Not applicableUs
Irbesartantablet300 mg/1oralSolco healthcare U.S., LLC2012-09-27Not applicableUs
Irbesartantablet300 mg/1oralAjanta Pharma Limited2015-01-20Not applicableUs
Irbesartantablet150 mg/1oralAmerican Health Packaging2013-06-122015-12-29Us
Irbesartantablet75 mg/1oralUnichem Pharmaceuticals (USA), Inc.2016-04-01Not applicableUs
Irbesartantablet300 mg/1oralAv Pak2015-10-27Not applicableUs
Irbesartantablet150 mg/1oralRoxane Laboratories, Inc.2012-10-15Not applicableUs
Irbesartantablet150 mg/1oralJubilant Cadista Pharmaceuticals Inc.2015-02-24Not applicableUs
Irbesartantablet300 mg/1oralUnichem Pharmaceuticals (USA), Inc.2016-04-01Not applicableUs
Irbesartantablet150 mg/1oralCamber Pharmaceuticals, Inc.2012-09-27Not applicableUs
Irbesartantablet, coated150 mg/1oralWatson Laboratories, Inc.2012-10-16Not applicableUs
Irbesartantablet150 mg/1oralbryant ranch prepack2013-05-10Not applicableUs
Irbesartantablet300 mg/300mgoralWestminster Pharmaceuticals, Llc2016-02-01Not applicableUs
Irbesartantablet150 mg/1oralSolco healthcare U.S., LLC2012-09-27Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
IrbesarranNot Available
LrbesartanNot Available
Brand mixtures
NameLabellerIngredients
Act Irbesartan/hctActavis Pharma Company
Apo-irbesartan/hctzApotex Inc
Auro-irbesartan HctAuro Pharma Inc
Ava-irbesartan/hctzAvanstra Inc
AvalideSanofi Aventis U.S. Llc
Avalide 150/12.5 mgSanofi Aventis Canada Inc
Avalide 300/12.5 mgSanofi Aventis Canada Inc
Dom-irbesartan-hctzDominion Pharmacal
Irbesartan and HydrochlorothiazideRoxane Laboratories, Inc.
Irbesartan HctSivem Pharmaceuticals Ulc
Irbesartan-hctzPro Doc Limitee
Irbesartan/hctActavis Pharma Company
Irbesartan/hctzSanis Health Inc
Jamp-irbesartan and HydrochlorothiazideJamp Pharma Corporation
Mint-irbesartan/hctzMint Pharmaceuticals Inc
Mylan-irbesartan HctzMylan Pharmaceuticals Ulc
Ntp-irbesartan/hctzTeva Canada Limited
Pendo-irbesartan-hctzPendopharm Division Of De Pharmascience Inc
PMS-irbesartan-hctzPharmascience Inc
Ran-irbesartan HctzRanbaxy Pharmaceuticals Canada Inc.
Ratio-irbesartan HctzTeva Canada Limited
Sandoz Irbesartan HctSandoz Canada Incorporated
Teva-irbesartan/hctzTeva Canada Limited
Van-irbesartan-hctzVanc Pharmaceuticals Inc
SaltsNot Available
Categories
UNIIJ0E2756Z7N
CAS number138402-11-6
WeightAverage: 428.5294
Monoisotopic: 428.232459548
Chemical FormulaC25H28N6O
InChI KeyInChIKey=YOSHYTLCDANDAN-UHFFFAOYSA-N
InChI
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)
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
SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biphenyltetrazoles and derivatives. These are organic compounds containing a biphenyl attached to a tetrazole. A carbon atom of the biphenyl moiety is boned to a carbon or the nitrogen atom of the tetrazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTetrazoles
Direct ParentBiphenyltetrazoles and derivatives
Alternative Parents
Substituents
  • Biphenyltetrazole
  • Biphenyl
  • Phenylmethylamine
  • Benzylamine
  • Benzenoid
  • Imidazolinone
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • 2-imidazoline
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of hypertension, as well as diabetic nephropathy with an elevated serum creatinine and proteinuria (>300 mg/day) in patients with type 2 diabetes and hypertension. Irbesartan is also used as a second line agent in the treatment of congestive heart failure.
PharmacodynamicsAngiotensin II, the principal pressor agent of the renin-angiotensin system, is responsible for effects such as vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Irbesartan is a specific competitive antagonist of AT1 receptors with a much greater affinity (more than 8500-fold) for the AT1 receptor than for the AT2 receptor and no agonist activity. Irbesartan's inhibition of angiotensin II binding to the AT1 receptor leads to multiple effects including vasodilation, a reduction in the secretion of vasopressin, and reduction in the production and secretion of aldosterone. The resulting effect is a decrease in blood pressure.
Mechanism of actionIrbesartan is a nonpeptide tetrazole derivative and an angiotensin II antagonist that selectively blocks the binding of angiotensin II to the AT1 receptor. In the renin-angiotensin system, angiotensin I is converted by angiotensin-converting enzyme (ACE) to form angiotensin II. Angiotensin II stimulates the adrenal cortex to synthesize and secrete aldosterone, which decreases the excretion of sodium and increases the excretion of potassium. Angiotensin II also acts as a vasoconstrictor in vascular smooth muscle. Irbesartan, by blocking the binding of angiotensin II to the AT1 receptor, promotes vasodilation and decreases the effects of aldosterone. The negative feedback regulation of angiotensin II on renin secretion is also inhibited, but the resulting rise in plasma renin concentrations and consequent rise in angiotensin II plasma concentrations do not counteract the blood pressure–lowering effect that occurs. The action of ARBs is different from ACE inhibitors, which block the conversion of angiotensin I to angiotensin II, meaning that the production of angiotensin II is not completely inhibited, as the hormone can be formed via other enzymes. Also, unlike ACE inhibitors, irbesartan and other ARBs do not interfere with response to bradykinins and substance P, which allows for the absence of adverse effects that are present in ACE inhibitors (eg. dry cough).
Related Articles
AbsorptionRapid and complete with an average absolute bioavailability of 60-80%. Food has no affect on bioavailability.
Volume of distribution
  • 53 to 93 L
Protein binding90% bound to serum proteins (primarily albumin and a1-acid glycoprotein) with negligible binding to cellular components of blood.
Metabolism

Hepatic. Irbesartan is metabolized via glucuronide conjugation and oxidation. In vitro studies of irbesartan oxidation by cytochrome P450 isoenzymes indicated irbesartan was oxidized primarily by 2C9; metabolism by 3A4 was negligible.

SubstrateEnzymesProduct
Irbesartan
SR 49498Details
Irbesartan
Irbesartan derivative M4Details
Irbesartan
Irbesartan derivative M5Details
Irbesartan
Irbesartan derivative M7Details
Irbesartan
Not Available
Irbesartan derivative M3Details
Irbesartan
Irbesartan derivative M8Details
Irbesartan derivative M4
Irbesartan derivative M1Details
Irbesartan derivative M1
Not Available
Irbesartan derivative M2Details
Irbesartan derivative M7
Irbesartan derivative M1Details
Irbesartan derivative M5
Irbesartan derivative M1Details
Irbesartan derivative M4
Not Available
Irbesartan derivative M6Details
Irbesartan derivative M6
Not Available
Irbesartan derivative M2Details
Route of eliminationIrbesartan is metabolized via glucuronide conjugation and oxidation. Irbesartan and its metabolites are excreted by both biliary and renal routes. Irbesartan is excreted in the milk of lactating rats.
Half life11-15 hours
Clearance
  • 157-176 mL/min
ToxicityHypotension and tachycardia; bradycardia might also occur from overdose, LD50=mg/kg(orally in rat)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Irbesartan Action PathwayDrug actionSMP00161
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9271
Caco-2 permeable-0.5679
P-glycoprotein substrateSubstrate0.7046
P-glycoprotein inhibitor IInhibitor0.639
P-glycoprotein inhibitor IINon-inhibitor0.6458
Renal organic cation transporterNon-inhibitor0.5091
CYP450 2C9 substrateNon-substrate0.6401
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.5749
CYP450 1A2 substrateNon-inhibitor0.6782
CYP450 2C9 inhibitorInhibitor0.5928
CYP450 2D6 inhibitorNon-inhibitor0.7584
CYP450 2C19 inhibitorInhibitor0.6619
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6192
Ames testNon AMES toxic0.5238
CarcinogenicityNon-carcinogens0.7492
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9171
hERG inhibition (predictor II)Non-inhibitor0.7728
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedoral
Tabletoral150 mg
Tabletoral150 mg/1
Tabletoral300 mg
Tabletoral300 mg/1
Tabletoral75 mg/1
Tabletoral75 mg
Tabletoral150 mg/150mg
Tabletoral300 mg/300mg
Tabletoral75 mg/75mg
Tablet, coatedoral150 mg/1
Tablet, coatedoral300 mg/1
Tablet, coatedoral75 mg/1
Tablet, film coatedoral150 mg/1
Tablet, film coatedoral300 mg/1
Tablet, film coatedoral75 mg/1
Tabletoral
Prices
Unit descriptionCostUnit
Avalide 300-25 mg tablet3.92USD tablet
Avalide 300-12.5 mg tablet3.63USD tablet
Avalide 150-12.5 mg tablet3.33USD tablet
Avapro 300 mg tablet2.64USD tablet
Avapro 150 mg tablet2.33USD tablet
Avapro 75 mg tablet2.21USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2057913 No1997-07-082011-03-20Canada
CA2177772 No2007-04-102016-05-30Canada
US5270317 No1994-09-302011-09-30Us
US5994348 Yes1995-12-072015-12-07Us
US6342247 Yes1995-12-072015-12-07Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point180-181 °CNot Available
logP6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00884 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Gennady Nisnevich, “Novel synthesis of irbesartan.” U.S. Patent US20040192713, issued September 30, 2004.

US20040192713
General References
  1. 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 ]
  2. Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. [PubMed:10822210 ]
  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 ]
External Links
ATC CodesC09DB05C09DA04C09CA04
AHFS Codes
  • 24:32.08
PDB EntriesNot Available
FDA labelDownload (263 KB)
MSDSDownload (57.3 KB)
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Irbesartan.
AlfuzosinAlfuzosin may increase the hypotensive activities of Irbesartan.
AliskirenAliskiren may increase the hyperkalemic activities of Irbesartan.
AmifostineIrbesartan may increase the hypotensive activities of Amifostine.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Irbesartan.
ArdeparinArdeparin may increase the hyperkalemic activities of Irbesartan.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Irbesartan.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Irbesartan.
BrimonidineBrimonidine may increase the antihypertensive activities of Irbesartan.
ButabarbitalButabarbital may increase the hypotensive activities of Irbesartan.
ButethalButethal may increase the hypotensive activities of Irbesartan.
CanagliflozinCanagliflozin may increase the hyperkalemic activities of Irbesartan.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Irbesartan.
CiprofloxacinIrbesartan may increase the arrhythmogenic activities of Ciprofloxacin.
CyclosporineIrbesartan may increase the hyperkalemic activities of Cyclosporine.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Irbesartan.
DiazoxideDiazoxide may increase the hypotensive activities of Irbesartan.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Irbesartan.
DrospirenoneIrbesartan may increase the hyperkalemic activities of Drospirenone.
DuloxetineIrbesartan may increase the orthostatic hypotensive activities of Duloxetine.
EplerenoneEplerenone may increase the hyperkalemic activities of Irbesartan.
HeparinHeparin may increase the hyperkalemic activities of Irbesartan.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Irbesartan.
HexobarbitalHexobarbital may increase the hypotensive activities of Irbesartan.
InfliximabThe risk or severity of adverse effects can be increased when Irbesartan is combined with Infliximab.
LevodopaIrbesartan may increase the orthostatic hypotensive activities of Levodopa.
LithiumThe serum concentration of Lithium can be increased when it is combined with Irbesartan.
MethohexitalMethohexital may increase the hypotensive activities of Irbesartan.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Irbesartan.
MolsidomineMolsidomine may increase the hypotensive activities of Irbesartan.
MoxonidineMoxonidine may increase the hypotensive activities of Irbesartan.
NicorandilNicorandil may increase the hypotensive activities of Irbesartan.
ObinutuzumabIrbesartan may increase the hypotensive activities of Obinutuzumab.
PentobarbitalPentobarbital may increase the hypotensive activities of Irbesartan.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Irbesartan.
PerindoprilThe risk or severity of adverse effects can be increased when Irbesartan is combined with Perindopril.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Irbesartan.
PrimidonePrimidone may increase the hypotensive activities of Irbesartan.
QuinineQuinine may increase the hypotensive activities of Irbesartan.
RisperidoneIrbesartan may increase the hypotensive activities of Risperidone.
RituximabIrbesartan may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Irbesartan.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Irbesartan.
TadalafilTadalafil may increase the antihypertensive activities of Irbesartan.
TolvaptanTolvaptan may increase the hyperkalemic activities of Irbesartan.
TorasemideThe metabolism of Torasemide can be decreased when combined with Irbesartan.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Irbesartan.
TreprostinilTreprostinil may increase the hypotensive activities of Irbesartan.
TriamtereneIrbesartan may increase the hyperkalemic activities of Triamterene.
TrimethoprimTrimethoprim may increase the hyperkalemic activities of Irbesartan.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Irbesartan.
VardenafilVardenafil may increase the antihypertensive activities of Irbesartan.
YohimbineYohimbine may decrease the antihypertensive activities of Irbesartan.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name:
AGTR1
Uniprot ID:
P30556
Molecular Weight:
41060.53 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Voigt JP, Bramlage P, Fink H: Hypophagic effect of the angiotensin AT1 receptor antagonist irbesartan in rats. Eur J Pharmacol. 2007 Jun 14;564(1-3):131-7. Epub 2007 Mar 3. [PubMed:17408613 ]
  3. Waeber B, Burnier M: AT1-receptor antagonism in hypertension: what has been learned with irbesartan? Expert Rev Cardiovasc Ther. 2003 May;1(1):23-33. [PubMed:15030294 ]
  4. Dol F, Martin G, Staels B, Mares AM, Cazaubon C, Nisato D, Bidouard JP, Janiak P, Schaeffer P, Herbert JM: Angiotensin AT1 receptor antagonist irbesartan decreases lesion size, chemokine expression, and macrophage accumulation in apolipoprotein E-deficient mice. J Cardiovasc Pharmacol. 2001 Sep;38(3):395-405. [PubMed:11486244 ]
  5. Martin G, Dol F, Mares AM, Berezowski V, Staels B, Hum DW, Schaeffer P, Herbert JM: Lesion progression in apoE-deficient mice: implication of chemokines and effect of the AT1 angiotensin II receptor antagonist irbesartan. J Cardiovasc Pharmacol. 2004 Feb;43(2):191-9. [PubMed:14716205 ]
  6. van den Meiracker AH, Admiraal PJ, Janssen JA, Kroodsma JM, de Ronde WA, Boomsma F, Sissmann J, Blankestijn PJ, Mulder PG, Man In 't Veld AJ, et al.: Hemodynamic and biochemical effects of the AT1 receptor antagonist irbesartan in hypertension. Hypertension. 1995 Jan;25(1):22-9. [PubMed:7843749 ]
  7. Carraway JW, Park S, McCune SA, Holycross BJ, Radin MJ: Comparison of irbesartan with captopril effects on cardiac hypertrophy and gene expression in heart failure-prone male SHHF/Mcc-fa(cp) rats. J Cardiovasc Pharmacol. 1999 Mar;33(3):451-60. [PubMed:10069682 ]
  8. Hope S, Brecher P, Chobanian AV: Comparison of the effects of AT1 receptor blockade and angiotensin converting enzyme inhibition on atherosclerosis. Am J Hypertens. 1999 Jan;12(1 Pt 1):28-34. [PubMed:10075381 ]
  9. Mazzolai L, Maillard M, Rossat J, Nussberger J, Brunner HR, Burnier M: Angiotensin II receptor blockade in normotensive subjects: A direct comparison of three AT1 receptor antagonists. Hypertension. 1999 Mar;33(3):850-5. [PubMed:10082498 ]
  10. Morsing P, Adler G, Brandt-Eliasson U, Karp L, Ohlson K, Renberg L, Sjoquist PO, Abrahamsson T: Mechanistic differences of various AT1-receptor blockers in isolated vessels of different origin. Hypertension. 1999 Jun;33(6):1406-13. [PubMed:10373224 ]
  11. Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. [PubMed:10822210 ]
  12. Croom KF, Plosker GL: Irbesartan: a review of its use in hypertension and diabetic nephropathy. Drugs. 2008;68(11):1543-69. [PubMed:18627212 ]
  13. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
Transcriptional activator activity, rna polymerase ii transcription factor binding
Specific Function:
Transcription factor that recognizes and binds to the enhancer heptamer motif 5'-TGA[CG]TCA-3'. Promotes activity of NR5A1 when phosphorylated by HIPK3 leading to increased steroidogenic gene expression upon cAMP signaling pathway stimulation.
Gene Name:
JUN
Uniprot ID:
P05412
Molecular Weight:
35675.32 Da
References
  1. Zhu ZS, Wang JM, Chen SL: Mesenteric artery remodeling and effects of imidapril and irbesartan on it in spontaneously hypertensive rats. World J Gastroenterol. 2004 May 15;10(10):1471-5. [PubMed:15133856 ]
  2. Cheng SM, Yang SP, Ho LJ, Tsao TP, Chang DM, Lai JH: Irbesartan inhibits human T-lymphocyte activation through downregulation of activator protein-1. Br J Pharmacol. 2004 Jul;142(6):933-42. Epub 2004 Jun 21. [PubMed:15210574 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 01:53