Irbesartan

Irbesartan

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 names	Avapro
AHFS/Drugs.com	monograph
MedlinePlus	a698009
Licence data	EMA:Link, US FDA:link
Pregnancy category	D (Au)
Legal status	S4 (Au), POM (UK), ℞-only (U.S.)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	60–80%
Protein binding	~90%
Metabolism	Hepatic (CYP2C9)
Biological half-life	11–15 hours
Excretion	Renal 20%, faecal 65%
Identifiers
CAS Number	138402-11-6 Y
ATC code	C09CA04 (WHO)
PubChem	CID: 3749
IUPHAR/BPS	589
DrugBank	DB01029 Y
ChemSpider	3618 Y
UNII	J0E2756Z7N Y
KEGG	D00523 Y
ChEBI	CHEBI:5959 Y
ChEMBL	CHEMBL1513 Y
Chemical data
Formula	C25H28N6O
Molecular mass	428.53 g/mol
SMILES O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4nnnn4)cc5
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) Y Key:YOSHYTLCDANDAN-UHFFFAOYSA-N Y
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Irbesartan (INN) /ɜːrbəˈsɑːrtən/ is an angiotensin II receptor antagonist used mainly for the treatment of hypertension. It 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

Main article: Angiotensin II receptor antagonist

Indications

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

Combination with diuretic

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.

Heart failure

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.

See also

• Angiotensin II receptor antagonist