6285. Moveltipril
Nomenclature
CAS number: 85856-54-8
N-(Cyclohexylcarbonyl)-d-alanyl-(2S)-3-mercapto-2-methylpropanoyl-l-proline; N-[3-(N-cyclohexanecarbonyl-d-alanylthio)-2-methylpropanoyl]-l-proline; (-)-N-[(S)-[3-(N-cyclohexylcarbonyl-d-alanyl)thio]-2-methylpropionyl]-l-proline; altiopril. C19H30N2O5S; mol wt 398.52.
C 57.26%, H 7.59%, N 7.03%, O 20.07%, S 8.05%.
Description and references
Angiotensin-converting enzyme (ACE) inhibitor; structural analog of captopril. Prepn: S. Tanaka et al., BE 893553 (1982 to Chugai), C.A. 98, 215995n (1983). Pharmacology: K. Sakai et al., Tohoku J. Exp. Med. 152, 363 (1987). Hemodynamic effects in dogs: K. Noguchi et al., Jpn. J. Pharmacol. 40, 373 (1986). Antihypertensive activity: J. Aono et al., Arch. Int. Pharmacodyn. 292, 203 (1988). Tissue specific ACE inhibitory activity: K. Sakai et al., ibid. 294, 228 (1988). Determn by radioimmunoassay: Y. Hinohara et al., J. Pharmacobio-Dyn. 11, 411 (1988).
Properties
Solid, mp 113-116°. [α]D +14.2° (c = 1.05 in methanol).Derivative
Calcium salt.Nomenclature
CAS number: 85921-53-5
MC-838; Lowpres (Chugai). C38H58CaN4O10S2; mol wt 835.10.
C 54.65%, H 7.00%, Ca 4.80%, N 6.71%, O 19.16%, S 7.68%.
Properties
Practically white powder, mp ≈190°. Bitter taste. [α]D20 -48 to -52° (c = 1 in methanol). Freely sol in water, methanol; sol in ethanol, chloroform. Practically insol in acetone, ethyl acetate. 10% aq soln has pH 5.5-6.5. Stable as aq soln and powder at room temp. LD50 in male, female mice, male, female rats (g/kg): all >10.0 orally; 2.1, 2.3, 1.3, 1.3 i.p.; 3.0, 3.8, 3.4, 3.9 s.c.; and in male, female dogs (g/kg): >6.0, >6.0 orally (Sakai).Therapeutic Category
Antihypertensive.
Keywords
ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives