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
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)
Safety
- Safety Statements
- 22-24/25
- Hazardous Substances Data
- 86541-75-5(Hazardous Substances Data)
N-Bromosuccinimide Price
- Product number
- B119858
- Product name
- BenazeprilFreeBase
- Packaging
- 2.5g
- Price
- $1825
- Updated
- 2021/12/16
- Product number
- API0001603
- Product name
- BENAZEPRIL
- Purity
- 95.00%
- Packaging
- 5G
- Price
- $2607.41
- Updated
- 2021/12/16
- Product number
- B1278
- Product name
- Benazepril
- Packaging
- 250mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 18510
- Product name
- Benazepril
- Packaging
- 25mg
- Price
- $1500
- Updated
- 2021/12/16
- Product number
- CS-1795
- Product name
- Benazepril
- Packaging
- 500mg
- Price
- $80
- Updated
- 2021/12/16
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
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View Lastest Price from Benazepril manufacturers
- Product
- Benazepril 86541-75-5
- Price
- US $50.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 50 tons
- Release date
- 2023-04-18
- 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
- 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