Benazepril hydrochloride

Base Information

• Chemical Name: Benazepril hydrochloride
• CAS No.: 86541-74-4
• Molecular Formula: C24H29ClN2O5
• Molecular Weight: 460.958
• Hs Code.: 29337900
• European Community (EC) Number: 630-414-2,680-262-6
• NSC Number: 758920
• UNII: N1SN99T69T
• DSSTox Substance ID: DTXSID9045922
• Wikidata: Q27105927
• NCI Thesaurus Code: C28862
• RXCUI: 235758
• ChEMBL ID: CHEMBL1694
• Mol file: 86541-74-4.mol

Synonyms:benazapril;benazepril;benazepril hydrochloride;benzazepril;Briem;CGS-14824-A;CGS-14824A;Cibacène;Cibacen;Labopal;Lotensin

Chemical Property of Benazepril hydrochloride

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 188-190 °C
• Boiling Point: 691.2 °C at 760 mmHg
• Flash Point: 371.8 °C
• PSA: 95.94000
• LogP: 3.83100
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: ~34 mg/mL, soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 460.1764997
• Heavy Atom Count: 32
• Complexity: 619

Purity/Quality:

98%-102% ^*data from raw suppliers

Benazepril Hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC2CCC3=CC=CC=C3N(C2=O)CC(=O)O.Cl
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCC3=CC=CC=C3N(C2=O)CC(=O)O.Cl
• Recent ClinicalTrials: Benazepril HCl 40 mg Tablets, Fed
• Recent EU Clinical Trials: A prospective, randomized, open label blinded end point probe trial to evaluate whether, at comparable blood pressure control, combined therapy with the ACE inhibitor Benazepril and the angiotensin II receptor blocker ARB Valsartan reduces progression to ESRD more effectively than Benazepril or Valsartan alone in high risk patients with type 2 diabetes and overt nephropathy VALID Study
• 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. 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.
• Uses: Used as an antihypertensive; angiotensin converting enzyme inhibitor.
• Therapeutic Function: Antihypertensive

Technology Process of Benazepril hydrochloride

There total 30 articles about Benazepril hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.6%

(2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (109010-61-9) → benazepril hydrochloride (86541-74-4,215447-89-5,88372-38-7)

Guidance literature:

With hydrogenchloride; In ethyl acetate;

Reference yield: 91.0%

ethyl (S)-2-(((S)-1-(2-(benzyloxy)-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3- yl)amino)-4-phenylbutanoate → benazepril hydrochloride (86541-74-4,215447-89-5,88372-38-7)

Guidance literature:

ethyl (S)-2-(((S)-1-(2-(benzyloxy)-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3- yl)amino)-4-phenylbutanoate; With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 3h;

With hydrogenchloride; In ethyl acetate; acetone; Reflux;

DOI:10.1007/s12039-021-01892-8

Reference yield: 25.0%

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + (3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt (86499-53-8) → benazepril hydrochloride (86541-74-4,215447-89-5,88372-38-7) + (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride (86541-77-7,215447-89-5,88372-38-7)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; Ambient temperature;

DOI:10.1021/jm00148a023

upstream raw materials:

2-oxo-4-phenylbutanoic acid ethyl ester

(3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt

(2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester

2-acetylnitrobenzene

Downstream raw materials:

benazepril

benazeprilate

Refernces

• 1、 -. "Synthesis method of benazepril intermediate and benazepril hydrochloride". Paragraph 0076; 0078-0079; 0081. . Retrieved 2020/03/13.
• 2、 -. "COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE". . . Retrieved 2015/02/05.