Benazepril hydrochloride
Benazepril hydrochloride Basic information
- Product Name:
- Benazepril hydrochloride
- Synonyms:
-
- 1h-1-benzazepine-1-aceticacid,2,3,4,5-tetrahydro-3-((1-(ethoxycarbonyl)-3-phe
- cgs14824a
- monohydrochloride,(s-(r*,r*))-nylpropyl)amino)-2-oxo
- BenazeprilHclC24H28N205.HC1
- 1H-1-Benzazepine-1-acetic acid, 3-(1S)-1-(ethoxycarbonyl)-3-phenylpropylamino-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, (3S)-
- 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,R*)]-
- CGS 14824A HCl
- Lotensin
- CAS:
- 86541-74-4
- MF:
- C24H29ClN2O5
- MW:
- 460.95
- EINECS:
- 630-414-2
- Product Categories:
-
- SONATA
- API
- Intermediates & Fine Chemicals
- Amines
- Aromatics
- Heterocycles
- Pharmaceuticals
- 86541-74-4
- Mol File:
- 86541-74-4.mol
Benazepril hydrochloride Chemical Properties
- Melting point:
- 188-190°C
- alpha
- D -141.0° (c = 0.9 in ethanol)
- storage temp.
- 2-8°C
- solubility
- DMSO: ~34 mg/mL, soluble
- form
- solid
- color
- white
- Merck
- 14,1031
- InChI
- InChI=1/C24H28N2O5.ClH/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28;/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28);1H/t19-,20-;/s3
- InChIKey
- VPSRQEHTHIMDQM-FKLPMGAJSA-N
- SMILES
- C12=CC=CC=C1CC[C@H](N[C@H](C(=O)OCC)CCC1C=CC=CC=1)C(=O)N2CC(=O)O.Cl |&1:8,10,r|
- CAS DataBase Reference
- 86541-74-4(CAS DataBase Reference)
Safety Information
- Safety Statements
- 22-24/25
- RIDADR
- 3077
- WGK Germany
- 2
- RTECS
- CX7065000
- HS Code
- 29337900
Benazepril hydrochloride Usage And Synthesis
Description
Benazepril hydrochloride is a long-acting and effective angiotensin-converting enzyme (ACE) inhibitor used to treat essential hypertension. It is the hydrochloride salt form of benazepril, which is a prodrug of benazeprilat. After hepatic cleavage of the ester group, benazepril is converted to benazeprilat. In healthy humans, it was well tolerated and showed no phmacokinetic interactions with furosemide, hydrochlorothiazide, chlorthalidone, digoxin, cimetidine, atenolol, or naproxen.
Chemical Properties
This substance is a white to off-white crystalline powder. It is highly soluble in water, ethanol, and methanol with a solubility of over 100 mg/mL.
Originator
Ciba-Geigy (Switzerland)
Uses
Benazepril HCl is an angiotensin-converting enzyme (ACE) inhibitors that is commonly used as a sedative, hypnotic, and antihypertensive medication. Benazepril is used alone or together with other medicines to treat high blood pressure (hypertension). It works by reducing the levels of certain chemicals that cause blood vessels to constrict, allowing for smoother blood flow.
Definition
ChEBI: Benazepril hydrochloride is a hydrochloride salt resulting from the reaction of benazepril with 1 mol eq. of hydrogen chloride. It is used as a prodrug for angiotensin-converting enzyme inhibitor benazeprilat in the treatment of hypertension and heart failure. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It contains a benazepril(1+).
brand name
Lotensin (Novartis);Cibacen.
Therapeutic Function
Antihypertensive
General Description
Benazepril is a prodrug of the angiotensin converting enzyme (ACE) inhibitor benazeprilat . It is metabolized to benazeprilat by hepatic esterases. Benazepril inhibits the in vitro enzymatic activity of partially purified ACE isolated from rabbit lung (IC50 = 2 nM). It decreases the triglyceride and total cholesterol levels in normotensive rats when administered at a dose of 30 mg/kg and decreases aortic atherosclerosis in cholesterol-fed rabbits when administered at a dose of 3 mg/kg per day. Benazepril (0.1-10 mg/kg per day) reduces blood pressure in spontaneously hypertensive rats. It also decreases proteinuria in cats with chronic kidney disease when administered at doses ranging from 0.5 to 1 mg/kg per day. Formulations containing benazepril have been used to treat hypertension, congestive heart failure, and chronic kidney disease in both human and veterinary medicine.
Biological Activity
Non-peptide angiotensin-converting enzyme (ACE) inhibitor. Reduces blood pressure and myocardial hypertrophy in spontaneous hypertensive rats.
Synthesis
Benazepril hydrochloride is prepared through the following steps:
Step 1: Preparation of (R)-ethyl 2-hydroxy-4-phenylbutyrate using ethyl 2-oxo-4-phenylbutyrate as a raw material and cinchonidine as a chiral ligand through asymmetric catalytic hydrogenation under high pressure.
Step 2: The intermediate obtained from step 1 reacts with p-nitrobenzenesulfonyl chloride or trifluoromethanesulfonic anhydride to obtain the corresponding sulfonate.
Step 3: The sulfonate obtained from step 2 undergoes nucleophilic substitution and salt hydrolysis with (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-benzazepine-1-tert-butyl acetate to obtain benazepril hydrochloride.
This procedure has been described in detail in documents such as CN110835319A, US4785089, WO02076375, EP206993, and CN105061312.
Mode of action
The mechanism of action of benazepril is to inhibit the activity of the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II Label, thereby alleviating a series of symptoms caused by angiotensin (elevated blood pressure, increased excitatory heart rate caused by vasodilation, insufficient cardiac output, etc.).
References
https://www.novartis.com/us-en/sites/novartis_us/files/lotrel.pdf
https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a216253b-27cb-42ef-b5a8-67fb05aafb88
Extrapyramidal side effect of donepezil hydrochloride in an elderly patient DOI: 10.1097/MD.0000000000019443
Use of convertible isocyanides for the synthesis of benazepril hydrochloride DOI: 10.1007/s12039-021-01892-8
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