Irbesartan

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Irbesartan
Irbesartan skeletal.svg
Systematic (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
Clinical data
Trade namesAvapro
AHFS/Drugs.commonograph
MedlinePlusa698009
Licence dataEMA:LinkUS FDA:link
Pregnancy cat.D (Au)
Legal statusS4 (Au), POM (UK), ℞-only (U.S.)
RoutesOral
Pharmacokinetic data
Bioavailability60–80%
Protein binding~90%
MetabolismHepatic (CYP2C9)
Half-life11–15 hours
ExcretionRenal 20%, faecal 65%
Identifiers
CAS number138402-11-6 YesY
ATC codeC09CA04
PubChemCID 3749
IUPHAR ligand589
DrugBankDB01029
ChemSpider3618 YesY
UNIIJ0E2756Z7N YesY
KEGGD00523 YesY
ChEBICHEBI:5959 YesY
ChEMBLCHEMBL1513 YesY
Chemical data
FormulaC25H28N6O 
Mol. mass428.53
 YesY (what is this?)  (verify)
 
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Irbesartan
Irbesartan skeletal.svg
Systematic (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
Clinical data
Trade namesAvapro
AHFS/Drugs.commonograph
MedlinePlusa698009
Licence dataEMA:LinkUS FDA:link
Pregnancy cat.D (Au)
Legal statusS4 (Au), POM (UK), ℞-only (U.S.)
RoutesOral
Pharmacokinetic data
Bioavailability60–80%
Protein binding~90%
MetabolismHepatic (CYP2C9)
Half-life11–15 hours
ExcretionRenal 20%, faecal 65%
Identifiers
CAS number138402-11-6 YesY
ATC codeC09CA04
PubChemCID 3749
IUPHAR ligand589
DrugBankDB01029
ChemSpider3618 YesY
UNIIJ0E2756Z7N YesY
KEGGD00523 YesY
ChEBICHEBI:5959 YesY
ChEMBLCHEMBL1513 YesY
Chemical data
FormulaC25H28N6O 
Mol. mass428.53
 YesY (what is this?)  (verify)

Irbesartan (INN) /ɜrbəˈsɑrtən/ is an angiotensin II receptor antagonist used mainly for the treatment of hypertension. Irbesartan was developed by Sanofi Research (now part of sanofi-aventis). It is jointly marketed by sanofi-aventis and Bristol-Myers Squibb under the trade names Aprovel, Karvea, and Avapro.

Clinical use[edit]

Indications[edit]

As with all angiotensin II receptor antagonists, irbesartan is indicated for the treatment of hypertension. Irbesartan may also delay progression of diabetic nephropathy and is also indicated for the reduction of renal disease progression in patients with type 2 diabetes,[1] hypertension and microalbuminuria (>30 mg/24 hours) or proteinuria (>900 mg/24 hours).[2]

Combination with diuretic[edit]

Irbesartan is also available in a combination formulation with a low dose thiazide diuretic, invariably hydrochlorothiazide, to achieve an additive antihypertensive effect. Irbesartan/hydrochlorothiazide combination preparations are marketed under similar trade names to irbesartan preparations, including Irda, CoIrda, CoAprovel, Karvezide, Avalide and Avapro HCT.

Heart failure[edit]

A large randomized trial following 4100+ men and women with heart failure and normal ejection fraction (>=45%) over 4+ years found no improvement in study outcomes or survival with irbesartan as compared to placebo.[3]

Market[edit]

BMS annual sales approx $1.3bn. Sanofi-aventis annual sales approx $2.1bn. In the United States, a generic version is available. Patent expired March 2012.

References[edit]

  1. ^ Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, Ritz E, Atkins RC, Rohde R, Raz I; Collaborative Study Group. (2001). "Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes". N Engl J Med 345 (12): 851–60. doi:10.1056/NEJMoa011303. PMID 11565517. 
  2. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  3. ^ Massie BM, Carson PE, McMurray JJ, Komajda M, McKelvie R, Zile MR, Anderson S, Donovan M, Iverson E, Staiger C, Ptaszynska A (December 2008). "Irbesartan in patients with heart failure and preserved ejection fraction". N. Engl. J. Med. 359 (23): 2456–67. doi:10.1056/NEJMoa0805450. PMID 19001508. 

See also[edit]