8103. Ramipril

Nomenclature

CAS number: 87333-19-5
[2S,3aS,6aS]-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid; N-(1S-carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3S-carboxylic acid; (2S,3aS,6aS)-1-[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid 1-ethyl ester; HOE-498; Altace (Aventis); Cardace (Aventis); Delix (Aventis); Pramace (AstraZeneca); Quark (Polifarma); Ramace (AstraZeneca); Triatec (Aventis); Tritace (Aventis); Unipril (Zambon); Vesdil (AstraZeneca).
C23H32N2O5; mol wt 416.51.
C 66.32%, H 7.74%, N 6.73%, O 19.21%.

Description and 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).

Chemical structure

Properties

Felty needles from ether, mp 109°. [α]D24 +33.2° (c = 1 in 0.1N 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).

Therapeutic Category

Antihypertensive.

Keywords

ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives