Title: Ramipril
CAS Registry Number: 87333-19-5
CAS Name: [2
S,3a
S,6a
S]-1-[(2
S)-2-[[(1
S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[
b]pyrrole-2-carboxylic acid
Synonyms: N-(1
S-carboethoxy-3-phenylpropyl)-
S-alanyl-
cis,endo-2-azabicyclo[3.3.0]octane-3
S-carboxylic acid; (2
S,3a
S,6a
S)-1-[(
S)-
N-[(
S)-1-carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[
b]pyrrole-2-carboxylic acid 1-ethyl ester
Manufacturers' Codes: HOE-498
Trademarks: Altace (Aventis); Cardace (Aventis); Delix (Aventis); Pramace (AstraZeneca); Quark (Polifarma); Ramace (AstraZeneca); Triatec (Aventis); Tritace (Aventis); Unipril (Zambon); Vesdil (AstraZeneca)
Molecular Formula: C23H32N2O5
Molecular Weight: 416.51
Percent Composition: C 66.32%, H 7.74%, N 6.73%, O 19.21%
Literature References: Angiotensin converting enzyme (ACE) inhibitor; converted to active, diacid metabolite,
ramiprilat. Prepn: V. Teetz
et al, EP 79022 (1983 to Hoechst A.G.),
C.A. 100, 52012h (1984); E. H. Gold
et al., US 4587258 (1986 to Schering Corp.); V. Teetz
et al., Arzneim.-Forsch. 34, 1399 (1984). Radioimmunoassay determn in human serum and plasma: H. G. Eckert
et al., ibid. 35, 1251 (1985). Toxicology: H. H. Donaubauer, D. Mayer,
ibid. 38, 14 (1988). Symposium on pharmacology and clinical efficacy:
Am. J. Cardiol. 59, 1D-177D (1987). Clinical trial in chronic nephropathy: P. Ruggenenti
et al., Lancet 352, 1252 (1998). Clinical prevention of cardiovascular events in high-risk patients: HOPE Study Investigators,
N. Engl. J. Med. 342, 145 (2000). Clinical trial in prevention of stroke: J. Bosch
et al., Br. Med. J. 324, 1 (2002).
Properties: Felty needles from ether, mp 109°. [a]D24 +33.2° (c = 1 in 0.1
N ethanolic HCl). LD50 (14 day) in male, female mice, male, female rats (mg/kg): 1194, 1158, 687, 608 i.v.; 10933, 10048, >10000, >10000 orally (Donaubauer, Mayer).
Melting point: mp 109°
Optical Rotation: [a]D24 +33.2° (c = 1 in 0.1
N ethanolic HCl)
Toxicity data: LD50 (14 day) in male, female mice, male, female rats (mg/kg): 1194, 1158, 687, 608 i.v.; 10933, 10048, >10000, >10000 orally (Donaubauer, Mayer)
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.