86541-78-8

Basic information

• Product Name: BENAZEPRILAT
• Synonyms: BENAZEPRILAT;BENAZEPRILAT HCL HYDRATE;Cibacen;BENAZEPRILAT HYDROCHLORIDE HYDRATE;1H-1-Benzazepine-1-acetic acid, 3-(1S)-1-carboxy-3-phenylpropylamino-2,3,4,5-tetrahydro-2-oxo-, (3S)-;(3S)-3-[[(S)-1-Carboxy-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid;CGS-14831;Benazepril Related Compound C (50 mg) ((3S)-3-[[(1S)-1- carboxy-3-phenylpropyl]amino-2,3,4,5-tetrahydro-2-oxo- 1H-1-benzazepine]-1-acetic acid)
• CAS NO: 86541-78-8
• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.44
• Product Categories: Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Aromatics;Heterocycles;Metabolites & Impurities;Chiral Reagents
• Mol File: 86541-78-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 270-272°C
• Boiling Point: 711.3 °C at 760 mmHg
• Flash Point: 384 °C
• Appearance: Crystalline Solid
• Density: 1.34 g/cm³
• Vapor Pressure: 3.09E-21mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly)
• PKA: 2.17±0.10(Predicted)
• CAS DataBase Reference: BENAZEPRILAT(CAS DataBase Reference)
• NIST Chemistry Reference: BENAZEPRILAT(86541-78-8)
• EPA Substance Registry System: BENAZEPRILAT(86541-78-8)

Safety Data

• Hazardous Substances Data: 86541-78-8(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Benazeprilat is a metabolite of Benazepril, which is used as an antihypertensive.

Definition

ChEBI: A benzazepine that is 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-pro-S hydrogen is replaced by the amino roup of (2S)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug benazepril in the treatment of hypertension and heart failure.

InChI:InChI=1/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18-/m0/s1

Upstream product

• 86541-75-5 benazepril 
• 86541-74-4 benazepril hydrochloride 
• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 
• 86499-52-7 (S)-3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 
• 94793-89-2 3-(S)-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepine-2-one 
• 86499-53-8 (3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt 
• 92278-69-8 ethyl 3-azido-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one-1-acetate 
• 97278-68-7 3-azido-2,3,4,5-tetrahydro-2-oxo-1 H-1-benzazepine 
• 86499-23-2 3-chloro-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one 
• 86499-22-1 3,3-dichloro-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 

Relevant articles and documents

Development and validation of different methods manipulating zero order and first order spectra for determination of the partially overlapped mixture benazepril and amlodipine: A comparative study

Three simple, selective, and accurate spectrophotometric methods have been developed and then validated for the analysis of Benazepril (BENZ) and Amlodipine (AML) in bulk powder and pharmaceutical dosage form. The first method is the absorption factor (AF

Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver

Carboxylesterases (EC 3.1.1.1) from human liver were purified using Q- Sepharose, Sephadex G-150, isoelectrofocusing and Con A-Sepharose. The calculated molecular mass of the pI 5.3 enzyme was 120 kDa and 61 kDa from the results of Sephadex G-150 gel filtration and SDS-polyacrylamide gel electrophoresis (PAGE), respectively, suggesting that this enzyme is a dimer. On the other hand, carboxylesterase pI 4.5, with a molecular-mass of 64 kDa, was a monomer. The activities of both enzymes were inhibited by typical serine enzyme inhibitors. Amino acid sequence analysis of the purified enzymes pI 5.3 and 4.5 showed high homology with rabbit carboxylesterase form 1 and 2, respectively. The results also suggested that carboxylesterase pI 5.3 is identical to the deduced amino acid sequence from cDNA for HUI, and that carboxylesterase pI 4.5 is identical to the deduced amino acid sequence from the cDNA registered as human carboxylesterase (hCE-2) in GenBank. We first purified carboxylesterase pI 4.5 and investigated its hydrolytic activity upon various drugs. The two enzymes differed in substrate specificity. Prodrugs of angiotensin-converting enzyme inhibitors, such as delapril and imidapril, were converted to active metabolites by carboxylesterase pI 5.3, but not by carboxylesterase pI 4.5. The hydrolysis velocity of temocapril by carboxylesterase pI 5.3 was 12-fold faster than by carboxylesterase pI 4.5. In contrast, aspirin oxybutynin and procaine were hydrolyzed by only carboxylesterase pI 4.5. We also found that an amide- linkage in drugs, except for that in aniracetam was not a good substrate for the two enzymes. Consequently, carboxylesterases pI 5.3 and 4.5 maybe involved in the metabolism of various drugs containing an ester-linkage.

Synthesis and biological properties of (carboxyalkyl)amino-substituted bicyclic lactam inhibitors of angiotensin converting enzyme

Syntheses of the potent angiotensin converting enzyme inhibitor (3S)-1-(carboxymethyl)-3-[[(1S)-1-carboxy-3-phenylpropyl]amino]-2,3,4,5 -tetrahydro-1H-[1]benzazepin-2-one (CGS 14831) and the related monoester prodrug (17a; CGS 14824A) are described together with preparative details for six- and eight-membered ring analogues. Inhibitory potencies and in vivo biological activity of the compounds are discussed. The data indicate that 17a has a biological profile comparable to that of enalapril.