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HomeProduct name listBenazepril hydrochloride

Benazepril hydrochloride

Synonym(s):(3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid hydrochloride;Benazepril hydrochloride

  • CAS NO.:86541-74-4
  • Empirical Formula: C24H29ClN2O5
  • Molecular Weight: 460.95
  • MDL number: MFCD01668249
  • EINECS: 630-414-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 08:26:49
Benazepril hydrochloride Structural

What is Benazepril hydrochloride?

Description

Benazepril hydrochloride, a prodrug of benazeprilat, is a long-acting angiotensionconverting enzyme (ACE) inhibitor useful in the treatment of essential hypertension. In healthy humans, it was well tolerated and showed no phmacokinetic interactions with furosemide, hydrochlorothiazide, chlorthalidone, digoxin, cimetidine, atenolol, or naproxen. Benazepril hydrochloride is under investigation as a cardiostirnulant.

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)

The Uses of Benazepril hydrochloride

sedative, hypnotic

The Uses of Benazepril hydrochloride

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.

What are the applications of Application

Benazepril hydrochloride is an angiotensin-converting enzyme (ACE) inhibitor

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

Properties of Benazepril hydrochloride

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
CAS DataBase Reference 86541-74-4(CAS DataBase Reference)

Safety information for Benazepril hydrochloride

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
Precautionary Statement Codes P201:Obtain special instructions before use.
P202:Do not handle until all safety precautions have been read and understood.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for Benazepril hydrochloride

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|

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