Lisinopril
Title: Lisinopril
CAS Registry Number: 83915-83-7
CAS Name: (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate
Manufacturers' Codes: MK-521
Trademarks: Acerbon (AstraZeneca); Alapril (Mediolanum); Carace (BMS); Coric (BMS); Novatec (Merck & Co.); Prinil (Merck & Co.); Prinivil (Merck & Co.); Vivatec (Merck & Co.); Zestril (AstraZeneca)
Molecular Formula: C21H31N3O5.2H2O
Molecular Weight: 441.52
Percent Composition: C 57.13%, H 7.99%, N 9.52%, O 25.37%
Literature References: Orally active angiotensin-converting enzyme (ACE) inhibitor. Prepn: A. A. Patchett et al., EP 12401; E. E. Harris et al., US 4374829 (1980, 1983 both to Merck & Co.); M. T. Wu et al., J. Pharm. Sci. 74, 352 (1985). Comprehensive description: D. P. Ip et al., Anal. Profiles Drug Subs. Excip. 21, 233-276 (1992). HPLC determn in urine: Y. C. Wong, B. G. Charles, J. Chromatogr. B 673, 306 (1995). Series of articles in hypertension and congestive heart failure: Am. J. Med. 85, Suppl. 3B, 1-59 (1988). Review of clinical efficacy in myocardial infarction: K. L. Goa et al., Drugs 52, 564-588 (1996). Clinical trial in diabetic retinopathy: N. Chaturvedi et al., Lancet 351, 28 (1998).
Properties: White to off-white crystalline, odorless powder. pKa1 (25°) 2.5; pKa2 4.0; pKa3 6.7; pKa4 10.1. Approx uv max (0.1N NaOH): 246, 254, 258, 261, 267 nm (A1%1cm 4.0, 4.5, 5.1, 5.1, 3.7); (0.1N HCl): 246, 253, 258, 264, 267 nm (A1%1cm 3.2, 3.9, 4.5, 3.0, 2.8). [a]25405 -120° (c = 1 in 0.25M pH 6.4 zinc acetate); [a]25436 -96° (c = 1 in 0.25M pH 6.4 zinc acetate). Partition coefficient at room temp (n-octanol/0.1M pH 7 phosphate buffer): 10.2 ±0.5. Soly (mg/ml): water 97; methanol 14; ethanol <0.1; acetone <0.1; acetonitrile <0.1; chloroform <0.1; DMF <0.1.
pKa: pKa1 (25°) 2.5; pKa2 4.0; pKa3 6.7; pKa4 10.1
Optical Rotation: [a]25405 -120° (c = 1 in 0.25M pH 6.4 zinc acetate); [a]25436 -96° (c = 1 in 0.25M pH 6.4 zinc acetate)
Log P: Partition coefficient at room temp (n-octanol/0.1M pH 7 phosphate buffer): 10.2 ±0.5
Absorption maximum: uv max (0.1N NaOH): 246, 254, 258, 261, 267 nm (A1%1cm 4.0, 4.5, 5.1, 5.1, 3.7)
 
Derivative Type: Mixture with hydrochlorothiazide
Trademarks: Prinzide (Merck & Co.); Zestoretic (AstraZeneca)
 
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.

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