ChemicalBook > CAS DataBase List > Benazepril

Benazepril

Product Name: 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
Formula Weight: 424.49
MOL File: 86541-75-5.mol

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Benazepril Property

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
InChIKey: XPCFTKFZXHTYIP-PMACEKPBSA-N
SMILES: N1(CC(O)=O)C2=CC=CC=C2CC[C@H](N[C@H](C(OCC)=O)CCC2=CC=CC=C2)C1=O
CAS DataBase Reference: 86541-75-5(CAS DataBase Reference)

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Safety

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

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: B119858
Product name: BenazeprilFreeBase
Packaging: 2.5g
Price: $1825
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0001603
Product name: BENAZEPRIL
Purity: 95.00%
Packaging: 5G
Price: $2607.41
Updated: 2021/12/16

ApexBio Technology

Product number: B1278
Product name: Benazepril
Packaging: 250mg
Price: $45
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 18510
Product name: Benazepril
Packaging: 25mg
Price: $1500
Updated: 2021/12/16

ChemScene

Product number: CS-1795
Product name: Benazepril
Packaging: 500mg
Price: $80
Updated: 2021/12/16

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Benazepril Chemical Properties,Usage,Production

Chemical Properties

Melting point 148-149°C. [α]D-159° (C=1.2, ethanol). Benazepril Hydrochloride: C24H28N2O5?HCl.[86541-74-4]. Crystallized from 3-pentanone-methanol (10:1), melting point 188-190°C. [α]αααγαιας (αααγαιας). [α]D-141.0° (C=0.9, ethanol). Benazeprilat (Bemzeprilat, (CGS-14831): C22H24N2O5.[86541-78-8]. The diacid of Benadryl. Melting point 270~272°C. [α]D-200.5° (C=1, 3% aqueous ammonium hydroxide).

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

Benazepril Preparation Products And Raw materials

Raw materials

4-Methylmorpholine Cinchonidine Sulfurous Acid 4-Nitrobenzenesulfonyl chloride Tert-butyl ester Benzyl 2-bromoacetate

Preparation Products

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View Lastest Price from Benazepril manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Benazepril 86541-75-5
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 100kg
Release date: 2021-11-02

Wuhan Han Sheng New Material Technology Co.，Ltd

Product: Benazepril 86541-75-5
Price: US $0.00-0.00/g
Min. Order: 100g
Purity: 99%
Supply Ability: 20 tons
Release date: 2023-07-17

Zhuozhou Wenxi import and Export Co., Ltd

Product: Benazepril 86541-75-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

86541-75-5, BenazeprilRelated Search:

PHENYL VALERATE Phenylhydrazine Glycine 3,4'-DIAMINODIPHENYLMETHANE 1,1'-Carbonyldiimidazole Propyl gallate Lithium diisopropylamide Propyl butyrate ALTRENOGEST Carbonyl iron powder S-ATBA Benazepril Related Compound G Benazepril hydrochloride NICKEL CARBONYL Benazepril Related Compound D Benazepril Related Compound F Hydrocortisone CORTISONE

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

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