1739. Candesartan

Nomenclature

CAS number: 139481-59-7
2-Ethoxy-1-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid; 2-ethoxy-1-[4-[2-(1H-tetrazol-5-yl)phenyl]benzyl]-7-benzimidazolecarboxylic acid; CV-11974.
C24H20N6O3; mol wt 440.45.
C 65.45%, H 4.58%, N 19.08%, O 10.90%.

Description and references

Angiotensin II type-1 receptor antagonist. Prepn: T. Naka et al., EP 459136; eidem, US 5196444 (1991, 1993 both to Takeda); K. Kubo et al., J. Med. Chem. 36, 2182, 2343 (1993). Pharmacology: Y. Shibouta et al., J. Pharmacol. Exp. Ther. 266, 114 (1993). Clinical pharmacology, pharmacokinetics: T. Ogihara et al., Clin. Ther. 16, 74 (1994). Series of clinical trials in chronic heart failure: Lancet 362, 759-781 (2003). Review of clinical experience in hypertension: S. E. Easthope, B. Jarvis, Drugs 62, 1253-1287 (2002); in heart failure: R. S. McKelvie, Expert Opin. Pharmacother. 7, 1945-1956 (2006).

Chemical structure

Properties

Colorless crystals from ethyl acetate + methanol, mp 183-185°.

Derivative

1-[[(Cyclohexyloxy)carbonyl]oxy]ethyl ester.

Nomenclature

CAS number: 145040-37-5
Candesartan cilexetil; TCV-116; Atacand (AstraZeneca); Amias (Takeda); Kenzen (Takeda).
C33H34N6O6; mol wt 610.66.
C 64.91%, H 5.61%, N 13.76%, O 15.72%.

Properties

Ester prodrug; hydrolyzed in vivo to the active carboxylic acid. Colorless crystals from ethanol + water, mp 163° (dec). Also reported as white to off-white powder, sparingly sol in methanol. Practically insol in water.

Therapeutic Category

Antihypertensive. In treatment of congestive heart failure.

Keywords

Angiotensin II Receptor Antagonist; Antihypertensive; Biphenyltetrazole Derivatives