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
License data	EU EMA: Aprovel US FDA: Irbesartan
Pregnancy category	D (Au)
Routes of administration	Oral
Legal status	S4 (Au), POM (UK), ℞-only (U.S.)
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
ATC code	C09CA04 (WHO)
PubChem	CID 3749
IUPHAR/BPS	589
DrugBank	DB01029
ChemSpider	3618
UNII	J0E2756Z7N
KEGG	D00523
ChEBI	CHEBI:5959
ChEMBL	CHEMBL1513
Chemical data
Formula	C25H28N6O
Molar 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) Key:YOSHYTLCDANDAN-UHFFFAOYSA-N
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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

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

• Angiotensin II receptor antagonist

References

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; Carson; McMurray; Komajda; McKelvie; Zile; Anderson; Donovan; Iverson; Staiger; Ptaszynska; i-Preserve (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.