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 cat.	D (Au)
Legal status	S4 (Au), POM (UK), ℞-only (U.S.)
Routes	Oral
Pharmacokinetic data
Bioavailability	60–80%
Protein binding	~90%
Metabolism	Hepatic (CYP2C9)
Half-life	11–15 hours
Excretion	Renal 20%, faecal 65%
Identifiers
CAS number	138402-11-6^Y
ATC code	C09CA04
PubChem	CID 3749
IUPHAR ligand	589
DrugBank	APRD00413
ChemSpider	3618^Y
UNII	J0E2756Z7N^Y
KEGG	D00523^Y
ChEBI	CHEBI:5959^Y
ChEMBL	CHEMBL1513^Y
Chemical data
Formula	C₂₅H₂₈N₆O
Mol. mass	428.53
SMILES	eMolecules & PubChem
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) ( /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.

1 Clinical use
- 1.1 Indications
- 1.2 Combination with diuretic
2 No benefits seen in trial for certain kind of heart failure
3 Market
4 References
5 See also

Clinical use

Main article: Angiotensin II receptor antagonist

Indications

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

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.

No benefits seen in trial for certain kind of 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]

Market

BMS annual sales approx $1.3bn. Sanofi-aventis annual sales approx $2.1bn. Patent expires in march 2012 currently.

References

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