8753. Spirapril
Nomenclature
CAS number: 83647-97-6
(8S)-7-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic
acid; (8S)-7[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic
acid 1-ethyl ester. C22H30N2O5S2; mol wt 466.61.
C 56.63%, H 6.48%, N 6.00%, O 17.14%, S 13.74%.
Description and references
Angiotensin-converting enzyme (ACE) inhibitor. Prepn: E. H. Gold et al., US 4470972 (1984 to Schering); E. M. Smith et al., J. Med. Chem. 32, 1600 (1989). Pharmacology: E. J. Sybertz et al., Arch. Int. Pharmacodyn. Ther. 286, 216 (1987); T. Baum et al., ibid. 230. Radioimmunoassay in plasma: M. Hossein-Nia et al., Ther. Drug Monit. 14, 234 (1992). Pharmacokinetics and evaluation in CHF: S. A. J. van den Broek et al., J. Cardiovasc. Pharmacol. 18, 614 (1991). Clinical evaluation in essential hypertension: G. P. Reams et al., J. Clin. Pharmacol. 33, 348 (1993). Review: P. Jerie, H.-J. Kremer, Cor Vasa 34, 82-87 (1992).
Derivative
Hemihydrate.Properties
White foam. [α]D26 29.5° (c = 0.2 in ethanol).Derivative
Hydrochloride.Nomenclature
CAS number: 94841-17-5
Sch-33844; TI-211-950; Renormax (Schering-Plough); Renpress (Sandoz); Sandopril (Sandoz). C22H30N2O5S2.HCl; mol wt 503.07.
C 52.52%, H 6.21%, N 5.57%, O 15.90%, S 12.75%, Cl 7.05%.
Properties
White solid, mp 192-194° (dec). [α]D26 11.2° (c = 0.4 in ethanol).Derivative
Diacid.Nomenclature
CAS number: 83602-05-5
Spiraprilat; spiraprilic acid; Sch-33861. C20H26N2O5S2; mol wt 438.56.
C 54.77%, H 5.98%, N 6.39%, O 18.24%, S 14.62%.
Properties
Hemihydrate, mp 163-165°. [α]D26 +4.1° (c = 0.4 in ethanol).Therapeutic Category
Antihypertensive.
Keywords
ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives