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Benazepril

CAS No.
86541-75-5
Chemical Name:
Benazepril
Synonyms
Briem;Benapril;Cibacene;Cibcen WS;genazepril;BENAZCPRIL;Cibacen WS;Benazepril;Benazapril;BENAZEPRIL MM
CBNumber:
CB5348020
Molecular Formula:
C24H28N2O5
Molecular Weight:
424.49
MDL Number:
MFCD00864466
MOL File:
86541-75-5.mol
Last updated:2024-07-02 08:55:11

Benazepril Properties

Melting point 148-149°
alpha D -159° (c = 1.2 in ethanol)
Boiling point 691.2±55.0 °C(Predicted)
Density 1.26±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO
pka 3.73±0.10(Predicted)
form Solid
color White to off-white
BCS Class 1
CAS DataBase Reference 86541-75-5(CAS DataBase Reference)
FDA UNII UDM7Q7QWP8
ATC code C09AA07

SAFETY

Risk and Safety Statements

Safety Statements  22-24/25
Hazardous Substances Data 86541-75-5(Hazardous Substances Data)

Benazepril price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC B119858 BenazeprilFreeBase 86541-75-5 2.5g $1825 2021-12-16 Buy
American Custom Chemicals Corporation API0001603 BENAZEPRIL 95.00% 86541-75-5 5G $2607.41 2021-12-16 Buy
ApexBio Technology B1278 Benazepril 86541-75-5 250mg $45 2021-12-16 Buy
Medical Isotopes, Inc. 18510 Benazepril 86541-75-5 25mg $1500 2021-12-16 Buy
ChemScene CS-1795 Benazepril 86541-75-5 500mg $80 2021-12-16 Buy
Product number Packaging Price Buy
B119858 2.5g $1825 Buy
API0001603 5G $2607.41 Buy
B1278 250mg $45 Buy
18510 25mg $1500 Buy
CS-1795 500mg $80 Buy

Benazepril Chemical Properties,Uses,Production

Originator

Lotensin,Novartis

Uses

Benazepril Free base is a non-sulfhydryl ACE inhibitor.

Definition

ChEBI: A benzazepine that is benazeprilat in which the carboxy group of the 2-amino-4-phenylbutanoic acid moiety has been converted to the corresponding ethyl ester. It is used (generally as its hydrochloride salt) as a prodrug for the angiotensin-converting enzy e inhibitor benazeprilat in the treatment of hypertension and heart failure.

Manufacturing Process

The synthesis of benzazepril based on a benzazepinone. It started by chlorination of lactam - 1,2,4,5-tetrahydrobenzo[b]azepin-2-one to the dichloro derivative 3,3-dichloro-1,2,4,5-tetrahydrobenzo[b]azepin-2-one. Catalytic reduction removed one of the gem chloro substituents to give 3- chloro-1,2,4,5-tetrahydrobenzo[b]azepin-2-one; the halogen was then displaced with sodium azide to give 3-azido-1,3,4,5- tetrahydrobenzo[b]azepin-2-one. Alkylation of the amide with ethyl bromoacetate in the presence of base yielded the ester (3-azido-2-oxo- 2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)acetic acid ethyl ester. Hydrogenation then converted the azide to an amino group to give 3-amino-2-oxo-2,3,4,5- tetrahydrobenzo[b]azepin-1-yl)acetic acid ethyl ester. It was then resolved by classical salt formation and crystallization. Saponification of the S enantiomer - S-(3-amino-2-oxo-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)acetic acid ethyl ester with sodium hydroxide afforded (3-amino-2-oxo-2,3,4,5- tetrahydrobenzo[b]azepin-1-yl)acetic acid. Reductive alkylation of it with 2- oxo-4-phenylbutyric acid ethyl ester and sodium cyanoborohydride gave the desired product as 70:30 mixture of diastereoisomers. The isolation of the predominant isomer gave benazepril. The epimerization occurred thermally and therefore required a sufficiently high temperature. The high temperature condition can be achieved by either using a high boiling-point solvent such as xylene or by heating the reaction mixture under pressure to increase its boiling-point temperature. Good results can be achieved in both polar and non-polar solvent systems. For example, both p-xylene and ethylene glycolwater systems are found suitable to conduct this process. The crude product acid 3-[(1-ethoxycarbonyl)-3-phenyl-(1S)-propylamino]-2,3,4,5-tetrahydro-2- oxo-1H-1-benzazepine-1-acetic acid was heated to reflux temperature for 30 hours in p-xylene. The mixture was cooled down to room temperature. Solvent removal resulted in a solid, which was then dried at reduced pressure to give a 98:2 diasteriomeric mixture as determined by HPLC, MP: 287°- 290°C. IR and 1H-NMR spectrum analysis. was confirmed the structure of product.

Therapeutic Function

Antihypertensive

Enzyme inhibitor

This ACE-directed pro-drug (FWfree-acid = 424.50 g/mol; CAS 86541-75-5), also known as 3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2,3,4,5- tetrahydro-2-oxo-(S-(R*,R*))-1H-1-benzazepine-1-acetic acid, Lotensin and CGS 14824A, is rapidly metabolized to its diacid benazeprilat (CGS 14831; FWfree-diacid = 396.44 g/mol), the latter a potent, long-acting inhibitor of peptidyl-dipeptidase A, or angiotensin I-converting enzyme, IC50 = 1.7 nM. Lotensin is used to treat hypertension, congestive heart failure, and chronic renal failure. The antihypertensive effects of benazepril begin as early as 30 min after a single dose, and those effects during consecutive dosing are also sustained for 24 h with a lesser diurnal variation in blood pressure

86541-74-4
86541-75-5
Synthesis of Benazepril from Benazepril hydrochloride
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View Lastest Price from Benazepril manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Benazepril pictures 2024-12-13 Benazepril
86541-75-5
US $0.00-0.00 / Kg/Drum 1KG 98%min 100kg WUHAN FORTUNA CHEMICAL CO., LTD
Benazepril pictures 2023-09-14 Benazepril
86541-75-5
US $0.00-0.00 / g 100g 99% 20 tons Wuhan Han Sheng New Material Technology Co.,Ltd
Benazepril pictures 2021-07-13 Benazepril
86541-75-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Benazepril pictures
  • Benazepril
    86541-75-5
  • US $0.00-0.00 / Kg/Drum
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Benazepril pictures
  • Benazepril
    86541-75-5
  • US $0.00-0.00 / g
  • 99%
  • Wuhan Han Sheng New Material Technology Co.,Ltd
  • Benazepril pictures
  • Benazepril
    86541-75-5
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Benazepril Spectrum

2-[(4s)-4-[[(1s)-1-ethoxycarbonyl-3-phenyl-propyl]amino]-5-oxo-6-azabicyclo[5.4.0]undeca-7,9,11-trien-6-yl]acetic acid genazepril BENAZEPRIL HCL, RELATED COMPOUND B(3S)-3-[[(1R)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-2,3,4,5-TETRAHYDRO-2-OXO-1H-1-BENAZAPINE-1-ACETIC ACID, MONOHYDROCHLORIDE USP STANDARD BENAZEPRIL HCL, MM(CRM STANDARD) BENAZEPRIL HCL, USP STANDARD BENAZEPRIL HCL USP(CRM STANDARD) BENAZEPRIL MM BENAZEPRIL MM(CRM STANDARD) BENAZEPRIL FREE BASE BENAZCPRIL 1H-1-Benzazepine-1-acetic acid, 3-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (3S)- 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, [S-(R*,R*)]- Benapril Briem Cibacen WS Cibacene (3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid [S-(R^<*>^,R^<*>^)]-3-[[1- (Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-lH-1-benzazepine-1-acetic acid Cibacene:Lotensin 2-[(4S)-4-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]-3-oxo-2-azabicyclo[5.4.0]undeca-7,9,11-trien-2-yl]acetic acid (3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid 2-[(3S)-3-[[(1S)-1-Ethoxycarbonyl-3-phenylpropyl]amino]-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-yl]acetic acid Cibcen WS Benazepril Benazapril 2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]aMino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid 2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid Benazepril USP/EP/BP 2-((S)-3-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetic acid Bifeprunox Impurity 16 86541-75-5 C24H28N2O5 API Antihypertensive Active Pharmaceutical Ingredients