1742. Candoxatril

Nomenclature

CAS number: 123122-55-4
[4(S)-cis]-4-[[[1-[3-[(2,3-Dihydro-1H-inden-5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]cyclohexanecarboxylic acid; (αS)-1-[(cis-4-carboxycyclohexyl)carbamoyl]-α-[(2-methoxyethoxy)methyl]cyclopentanepropionic acid α-5-indanyl ester; (S)-cis-4-[1-[2-(5-indanyloxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxamido]-1-cyclohexanecarboxylic acid; UK-79300.
C29H41NO7; mol wt 515.64.
C 67.55%, H 8.01%, N 2.72%, O 21.72%.

Description and references

Neutral endopeptidase inhibitor. Prepn: I. T. Barnish et al., EP 274234; eidem, US 5030654 (1988, 1991 both to Pfizer). Enzyme inhibition and pharmacology: J. C. Danilewicz et al., Biochem. Biophys. Res. Commun. 164, 58 (1989). Clinical pharmacokinetics and effect on plasma ANP: J. G. Motwani et al., Clin. Pharmacol. Ther. 54, 661 (1993). Clinical evaluation in congestive heart failure: C. D. Kimmelstiel et al., Cardiology 87, 46 (1996).

Chemical structure

Properties

White crystals, mp 107-109°. [α]D -5.8° (c = 1 in methanol).

Derivative

Diacid.

Nomenclature

CAS number: 123122-54-3
Candoxatrilat; UK-73967.
C20H33NO7; mol wt 399.48.
C 60.13%, H 8.33%, N 3.51%, O 28.04%.

Properties

White crystals from ethyl acetate, mp 108.5-109.1°. [α]D +1.4° (c = 1 in methanol).

Therapeutic Category

In treatment of congestive heart failure.

Keywords

Neutral Endopeptidase Inhibitor