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 hydrochloride

• ChemBase ID: 72608
• Molecular Formular: C24H29ClN2O5
• Molecular Mass: 460.95046
• Monoisotopic Mass: 460.17649972
• SMILES: N1(C(=O)[C@H](CCc2c1cccc2)N[C@H](C(=O)OCC)CCc1ccccc1)CC(=O)O.Cl
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H]1CCc2c(N(C1=O)CC(=O)O)cccc2)CCc1ccccc1.Cl
• InChI: InChI=1S/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-;/m0./s1
• InChIKey: VPSRQEHTHIMDQM-FKLPMGAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 hydrochloride
• IUPAC Traditional name: benazepril hydrochloride; 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 hydrochloride
• Synonyms: (3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid hydrochloride; Benazepril hydrochloride; Lotensin; Benazepril hydrochloride; 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 hydrochloride; Cibacen; (3S)-3-[[(1S)-1-(乙氧羰基)-3-苯丙基]氨基]-2,3,4,5-四氢-2-氧代-1H-1-苯并氮杂卓-1-乙酸 盐酸盐; 贝那普利 盐酸盐

Database IDs

• CAS Number: 86541-74-4
• MDL Number: MFCD00895734
• PubChem SID: 162037533; 24724409
• PubChem CID: 5362123

CALCULATED PROPERTIES

• Acid pKa: 3.52708
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3033304
• LogD (pH = 7.4): 0.0697504
• Log P: 1.5374391
• Molar Refractivity: 115.2279 cm^3
• Polarizability: 45.29758 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; H2O: >5 mg/mL; Methanol; Water
• Apperance: solid; White Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: CX7065000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: ACE
• Mechanism of Action: Angiotensin-converting enzyme inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: HCl; Hydrochloride
• Application(s): Antihypertensive agent
• Empirical Formula (Hill Notation): C24H28N2O5 · HCl

DETAILS

Selleck Chemicals - S1284

Research Area: Cardiovascular Disease
Biological Activity:
Benazepril is a medication used to treat high blood pressure (hypertension), congestive heart failure, and chronic renal failure. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor. [1]

Sigma Aldrich - B0935

Biochem/physiol Actions
Benazepril is a long-acting angiotensin converting enzyme (ACE) inhibitor.

Sigma Aldrich - 32423

Biochem/physiol Actions
Benazepril is a long-acting angiotensin converting enzyme (ACE) inhibitor.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B119750

Used as an antihypertensive; angiotensin converting enzyme inhibitor.

REFERENCES

• http://www.rxlist.com/lotensin-hct-drug.htm
• Schaller, M.D., et al.: Eur. J. Clin. Pharmacol., 28, 267 (985)
• Colfer, H.T., et al.: Am. J. Cardiol., 70, 354 (1992)
• Watthey, J.W.H. et al., J. Med. Chem., 1985, 28, 1511, (synth, pharmacol)
• Kaiser, G. et al., J. Chromatogr., 1987, 419, 123, (glc, ms)
• Boyer, S.K. et al., Helv. Chim. Acta, 1988, 71, 337, (synth, ir, pmr)
• Webb, R.L. et al., Cardiovasc. Drug Rev., 1990, 8, 89, (rev)
• Kunick, C., Pharm. Ztg., 1994, 139, 26, (rev)
• ACE Inhibitors: Current Use and Future Prospects, (Ed. Schachter, M.), Martin Dunitz, 1995, (book)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 827