1031. Benazepril

Nomenclature

CAS number: 86541-75-5
(3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid; (3S)-1-(carboxymethyl)-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one; (3S)-3-[[(1S)-1-carboxy-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid 3-ethyl ester.
C24H28N2O5; mol wt 424.49.
C 67.91%, H 6.65%, N 6.60%, O 18.85%.

Description and references

Angiotensin converting enzyme (ACE) inhibitor. Hydrolyzed in vivo to the active diacid metabolite. Prepn: J. W. H. Watthey, EP 72352; idem, US 4410520 (both 1983 to Ciba-Geigy); J. W. H. Watthey et al., J. Med. Chem. 28, 1511 (1985). Clinical pharmacology: M. D. Schaller et al., Eur. J. Clin. Pharmacol. 28, 267 (1985). GC-MS determn in plasma and urine: A. Sioufi et al., J. Chromatogr. 434, 239 (1988). Pharmacokinetics of benazepril and benazeprilat: G. Kaiser et al., Biopharm. Drug Dispos. 10, 365 (1989). Multicenter clinical trial in hypertension: M. Moser et al., ibid. 49, 322 (1991); in congestive heart failure: H. T. Colfer et al., Am. J. Cardiol. 70, 354 (1992).

Chemical structure

Properties

mp 148-149°. [α]D 159° (c = 1.2 in ethanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 86541-74-4
CGS-14824A; Briem (Fabre); Cibacen (Novartis); Fortekor (Novartis); Lotensin (Novartis).
C24H28N2O5.HCl; mol wt 460.95.
C 62.54%, H 6.34%, N 6.08%, O 17.35%, Cl 7.69%.

Properties

Crystals from 3-pentanone + methanol (10:1), mp 188-190°. [α]D 141.0° (c = 0.9 in ethanol). Sol in water, ethanol, methanol.

Derivative

Diacid.

Nomenclature

CAS number: 86541-78-8
Benazeprilat; CGS-14831.
C22H24N2O5; mol wt 396.44.
C 66.65%, H 6.10%, N 7.07%, O 20.18%.

Properties

mp 270-272°. [α]D 200.5° (c = 1 in 3% aqueous NH4OH).

Therapeutic Category

Antihypertensive.

Therapeutic Category (Veterinary)

In treatment of congestive heart failure in dogs.

Keywords

ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives