Quinapril
Title: Quinapril
CAS Registry Number: 85441-61-8
CAS Name: (3S)-2-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
Additional Names: (S)-2-[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid 1-ethyl ester
Molecular Formula: C25H30N2O5
Molecular Weight: 438.52
Percent Composition: C 68.47%, H 6.90%, N 6.39%, O 18.24%
Literature References: Angiotensin converting enzyme (ACE) inhibitor. Prepn: M. L. Hoefle, S. Klutchko, EP 49605; eidem, US 4344949 (both 1982 to Warner-Lambert); S. Klutchko et al., J. Med. Chem. 29, 1953 (1986). Synthesis of purified crystalline form: O. P. Goel, U. Krolls, US 4761479 (1988 to Warner-Lambert). Pharmacology: H. R. Kaplan et al., Fed. Proc. 43, 1326 (1984); M. J. Ryan et al., ibid. 1330. HPLC determn of quinapril and quinaprilat in plasma and urine: H. Hengy, M. Most, J. Liq. Chromatogr. 11, 517 (1988). Toxicity data: H. R. Kaplan et al., Angiology 40, 335 (1989). Review of pharmacology, pharmacokinetics and clinical experience in congestive heart failure and hypertension: C. R. Culy, B. Jarvis, Drugs 62, 339-385 (2002).
 
Derivative Type: Hydrochloride
CAS Registry Number: 82586-55-8
Manufacturers' Codes: CI-906; PD-109452-2
Trademarks: Accupril (Parke-Davis); Accupro (Pfizer); Acequin (Recordati); Acuitel (Pfizer); Korec (Sanofi-Aventis); Quinazil (Malesci)
Molecular Formula: C25H30N2O5.HCl
Molecular Weight: 474.98
Percent Composition: C 63.22%, H 6.58%, N 5.90%, O 16.84%, Cl 7.46%
Properties: Crystals from ethyl acetate-toluene, mp 120-130°. [a]D23 +14.5° (c = 1.2 in ethanol) (Klutchko). Also reported as white crystalline solid from acetonitrile, mp 119-121.5°. [a]D25 +15.4° (c = 2 in methanol) (Goel, Krolls). Freely sol in aq solvents. LD50 in male, female mice, rats (mg/kg): 1739, 1840, 4280, 3541 orally; 504, 523, 158, 107 i.v. (Kaplan, 1989).
Melting point: mp 120-130°; mp 119-121.5°
Optical Rotation: [a]D23 +14.5° (c = 1.2 in ethanol) (Klutchko); [a]D25 +15.4° (c = 2 in methanol) (Goel, Krolls)
Toxicity data: Freely sol in aq solvents. LD50 in male, female mice, rats (mg/kg): 1739, 1840, 4280, 3541 orally; 504, 523, 158, 107 i.v. (Kaplan, 1989)
 
Derivative Type: Diacid
CAS Registry Number: 82768-85-2
Additional Names: Quinaprilat
Manufacturers' Codes: CI-928
Trademarks: Accuprin (Pfizer)
Molecular Formula: C23H26N2O5
Molecular Weight: 410.46
Percent Composition: C 67.30%, H 6.38%, N 6.82%, O 19.49%
Properties: Active metabolite. Hydrate, crystals from methanol-ethyl ether, mp 166-168°. [a]D23 +20.9° (c = 1 in methanol).
Melting point: mp 166-168°
Optical Rotation: [a]D23 +20.9° (c = 1 in methanol)
 
Derivative Type: Mixture with hydrochlorothiazide
Trademarks: Accuretic (Parke-Davis); Acequide (Recordati); Koretic (Sanofi-Aventis)
 
Therap-Cat: Antihypertensive. In treatment of congestive heart failure.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.

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