Spirapril
Title: Spirapril
CAS Registry Number: 83647-97-6
CAS Name: (8S)-7-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
Additional Names: (8S)-7[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid 1-ethyl ester
Molecular Formula: C22H30N2O5S2
Molecular Weight: 466.61
Percent Composition: C 56.63%, H 6.48%, N 6.00%, O 17.14%, S 13.74%
Literature 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 Type: Hemihydrate
Properties: White foam. [a]D26 -29.5° (c = 0.2 in ethanol).
Optical Rotation: [a]D26 -29.5° (c = 0.2 in ethanol)
 
Derivative Type: Hydrochloride
CAS Registry Number: 94841-17-5
Manufacturers' Codes: Sch-33844; TI-211-950
Trademarks: Renormax (Schering-Plough); Renpress (Sandoz); Sandopril (Sandoz)
Molecular Formula: C22H30N2O5S2.HCl
Molecular Weight: 503.07
Percent Composition: 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). [a]D26 -11.2° (c = 0.4 in ethanol).
Melting point: mp 192-194° (dec)
Optical Rotation: [a]D26 -11.2° (c = 0.4 in ethanol)
 
Derivative Type: Diacid
CAS Registry Number: 83602-05-5
Additional Names: Spiraprilat; spiraprilic acid
Manufacturers' Codes: Sch-33861
Molecular Formula: C20H26N2O5S2
Molecular Weight: 438.56
Percent Composition: C 54.77%, H 5.98%, N 6.39%, O 18.24%, S 14.62%
Properties: Hemihydrate, mp 163-165°. [a]D26 +4.1° (c = 0.4 in ethanol).
Melting point: mp 163-165°
Optical Rotation: [a]D26 +4.1° (c = 0.4 in ethanol)
 
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.

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