5083. Irbesartan
Nomenclature
CAS number: 138402-11-6
2-Butyl-3-[[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one; 2-butyl-3-[p-(o-1H-tetrazol-5-ylphenyl)benzyl]-1,3-diazaspiro[4.4]non-1-en-4-one; 2-n-butyl-4-spirocyclopentane-1-[(2′-(tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one; BMS-186295; SR-47436; Aprovel (Sanofi-Synthelabo); Avapro (Sanofi-Synthelabo). C25H28N6O; mol wt 428.53.
C 70.07%, H 6.59%, N 19.61%, O 3.73%.
Description and references
Angiotensin II type 1 (AII1)-receptor antagonist. Prepn: C. Bernhart et al., WO 9114679; eidem, US 5270317 (1991, 1993 both to Sanofi); eidem et al., J. Med. Chem. 36, 3371 (1993). HPLC determn in plasma and urine: S.-Y. Chang et al., J. Chromatogr. B 702, 149 (1997). Metabolism: T. J. Chando et al., Drug Metab. Dispos. 26, 408 (1998). Review of pharmacology and clinical efficacy: J. C. Gillis, A. Markham, Drugs 54, 885-902 (1997). Renoprotective effect in diabetic nephropathy: E. J. Lewis et al., N. Engl. J. Med. 345, 851 (2001); H.-H. Parving et al., ibid. 870.
Properties
Crystals from 96% ethanol, mp 180-181°.Therapeutic Category
Antihypertensive.
Keywords
Angiotensin II Receptor Antagonist; Antihypertensive; Biphenyltetrazole Derivatives