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 names Avapro
AHFS/Drugs.com monograph
MedlinePlus a698009
Licence data EMA:Link, US FDA:link
Pregnancy
category
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 YesY
ATC code C09CA04 (WHO)
PubChem CID: 3749
IUPHAR/BPS 589
DrugBank DB01029 YesY
ChemSpider 3618 YesY
UNII J0E2756Z7N YesY
KEGG D00523 YesY
ChEBI CHEBI:5959 YesY
ChEMBL CHEMBL1513 YesY
Chemical data
Formula C25H28N6O
Molecular mass 428.53 g/mol
  • O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4nnnn4)cc5
  • 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) YesY
  • Key:YOSHYTLCDANDAN-UHFFFAOYSA-N YesY
  (verify)

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

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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,[1] hypertension and microalbuminuria (>30 mg/24 hours) or proteinuria (>900 mg/24 hours).[2]

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.[3]

See also

References

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  2. Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
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