Irbesartan

Irbesartan
Clinical data
Trade names	Avapro
AHFS/Drugs.com	Monograph
MedlinePlus	a698009
License data	EU EMA: by INN; US FDA: Irbesartan;
Pregnancy; category	AU: D; ;
Routes of; administration	Oral
ATC code	C09CA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: WARNINGRx only;
Pharmacokinetic data
Bioavailability	60% to 80%
Protein binding	~90%
Metabolism	Hepatic (CYP2C9)
Elimination half-life	11 h to 15 h
Excretion	Renal 20%, faecal 65%
Identifiers
	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;
CAS Number	138402-11-6 ;
PubChem CID	3749;
IUPHAR/BPS	589;
DrugBank	DB01029 ;
ChemSpider	3618 ;
UNII	J0E2756Z7N;
KEGG	D00523 ;
ChEBI	CHEBI:5959 ;
ChEMBL	ChEMBL1513 ;
CompTox Dashboard (EPA)	DTXSID0023169 ;
ECHA InfoCard	100.119.966
Chemical and physical data
Formula	C25H28N6O
Molar mass	428.53 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4n[nH]nn4)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 ;
	(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

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,^[2] hypertension and microalbuminuria (>30 mg/24 h) or proteinuria (>900 mg/24 h).^[3]

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

I-PRESERVE, 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.^[4]

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ 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.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[Lewis-2001-2] 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.

[Rossi2006-3] Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3

[pmid19001508-4] 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.

[1]

[2]

[3]

[4]

v t e Antihypertensive drugs acting on the renin–angiotensin system (C09)
ACE inhibitors ("-pril")	Sulfhydryl-containing: Captopril Rentiapril Zofenopril (+nebivolol) Dicarboxylate-containing: Enalapril^# (+lercanidipine, +nitrendipine) Benazepril (+amlodipine, +pimobendan) Cilazapril Delapril (+manidipine) Imidapril Lisinopril (+amlodipine, +HCT) Moexipril Perindopril (+amlodipine, +bisoprolol, +indapamide, +amlodipine and indapamide, +bisoprolol and amlodipine, +bisoprolol, amlodipine, and indapamide) Quinapril (+HCT) Ramipril (+amlodipine, +amlodipine and HCT, +bisoprolol, +felodipine) Spirapril Temocapril Trandolapril (+verapamil) Phosphonate-containing: Ceronapril Fosinopril (+HCT) Other/ungrouped: Alacepril
AIIRAs ("-sartan")	Azilsartan Candesartan (+amlodipine, +amlodipine and HCT) Eprosartan Fimasartan Irbesartan (+amlodipine, +amlodipine and HCT, +HCT) Losartan (+amlodipine, +HCT) Olmesartan (+amlodipine, +amlodipine and HCT, +HCT) Tasosartan^§ Telmisartan (+amlodipine, +amlodipine and HCT, +HCT) Valsartan (+aliskiren, +amlodipine, +amlodipine and HCT, +HCT, +lercanidipine, +nebivolol, +sacubitril)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine, +HCT, +amlodipine and HCT) Remikiren^§
Dual ACE/NEP inhibitors	Gemopatrilat Ilepatril Omapatrilat Sampatrilat
Neprilysin inhibitors	Sacubitril (+valsartan)
Other	Sparsentan
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Clinical use

Indications

Combination with diuretic

Heart failure

See also

References