Benazepril

Title: Benazepril
CAS Registry Number: 86541-75-5
CAS Name: (3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid
Additional Names: (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
Molecular Formula: C24H28N2O5
Molecular Weight: 424.49
Percent Composition: C 67.91%, H 6.65%, N 6.60%, O 18.85%
Literature 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).
Properties: mp 148-149°. [a]D -159° (c = 1.2 in ethanol).
Melting point: mp 148-149°
Optical Rotation: [a]D -159° (c = 1.2 in ethanol)
Derivative Type: Hydrochloride
CAS Registry Number: 86541-74-4
Manufacturers' Codes: CGS-14824A
Trademarks: Briem (Fabre); Cibacen (Novartis); Fortekor (Novartis); Lotensin (Novartis)
Molecular Formula: C24H28N2O5.HCl
Molecular Weight: 460.95
Percent Composition: 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°. [a]D -141.0° (c = 0.9 in ethanol). Sol in water, ethanol, methanol.
Melting point: mp 188-190°
Optical Rotation: [a]D -141.0° (c = 0.9 in ethanol)
Derivative Type: Diacid
CAS Registry Number: 86541-78-8
Additional Names: Benazeprilat
Manufacturers' Codes: CGS-14831
Molecular Formula: C22H24N2O5
Molecular Weight: 396.44
Percent Composition: C 66.65%, H 6.10%, N 7.07%, O 20.18%
Properties: mp 270-272°. [a]D -200.5° (c = 1 in 3% aqueous NH4OH).
Melting point: mp 270-272°
Optical Rotation: [a]D -200.5° (c = 1 in 3% aqueous NH4OH)
Therap-Cat: Antihypertensive.
Therap-Cat-Vet: In treatment of congestive heart failure in dogs.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.
Bencyclane Bendamustine Bendazac Bendazol Bendiocarb

Benazepril
Benazepril.svg
Systematic (IUPAC) name
2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-
Clinical data
Trade names Lotensin
AHFS/Drugs.com monograph
MedlinePlus a692011
Pregnancy cat. D
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Protein binding 96.7%
Metabolism Hepatic glucuronidation
Half-life 10-11 hours
Excretion Renal and biliary
Identifiers
CAS number 86541-75-5 YesY
ATC code C09AA07
PubChem CID 5362124
DrugBank DB00542
ChemSpider 4514935 YesY
UNII UDM7Q7QWP8 YesY
ChEBI CHEBI:3011 YesY
ChEMBL CHEMBL838 YesY
Chemical data
Formula C24H28N2O5 
Mol. mass 424.49 g/mol
 YesY (what is this?)  (verify)

Benazepril, brand name Lotensin (Novartis), is a medication used to treat high blood pressure (hypertension), congestive heart failure, and chronic renal failure. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor.