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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)
BCS Class
1
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

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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Benazepril Suppliers

Canada 2 China 99 Europe 3 Germany 1 India 10 United Kingdom 7 United States 27 Global 149
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9901
Advantage
58
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4863
Advantage
58
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3750
Advantage
55
TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7934
Advantage
58
Wuhan Dahua Pharmaceutical Co., Ltd.
Tel
027-59262863 13277907145 3091977954
Fax
027-59420980
Country
China
ProdList
4951
Advantage
58
Shanghai Mixiu Chemical Co., Ltd.
Tel
18101936766
Fax
021-58583907
Email
eileen@shmychem.com
Country
China
ProdList
351
Advantage
55
Hefei TNJ Chemical Industry Co.,Ltd.
Tel
551-65418679 15837135945
Fax
0551-65418697
Email
info@tnjchem.com
Country
China
ProdList
1889
Advantage
62
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View Lastest Price from Benazepril manufacturers

Hebei Duling International Trade Co. LTD
Product
Benazepril 86541-75-5
Price
US $50.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
50 tons
Release date
2023-04-18
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

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
  • Active Pharmaceutical Ingredients