3452. Dropropizine
Nomenclature
CAS number: 17692-31-8
3-(4-Phenyl-1-piperazinyl)-1,2-propanediol; 1-phenyl-4-(2,3-dihydroxypropyl)piperazine; 1-(2,3-dihydroxypropyl)-4-phenylpiperazine; 1-phenyl-4-(2,3-dihydroxypropyl)diethylenediamine; UCB-1967; Ribex (Formenti). C13H20N2O2; mol wt 236.31.
C 66.07%, H 8.53%, N 11.85%, O 13.54%.
Description and references
Cough suppressive phenylpiperazine derivative. Prepn: H. G. Morren, BE 601394; eidem, US 3163649 (1961, 1964 to UCB); H. Howell et al., J. Org. Chem. 27, 1709 (1962); J. Bourdais, Bull. Soc. Chim. Fr. 1968, 3246. Prepn of enantiomers: M. Borsa et al., EP 147847; eidem, US 4699911 (1985, 1987 both to Dompé). LC-MS-MS determn in plasma: Y. Tang et al., J. Chromatogr. B 819, 185 (2005). Pharmacology: K. Cartwright, J. L. Paterson, J. Pharm. Pharmacol. 23, Suppl., 247S (1971). Controlled clinical trials: G. C. Moreo et al., Gazz. Med. Ital. 140, 409 (1981); A. Ravetta, M. Ravetta, ibid. 141, 531 (1982). Chronic oral toxicity: P. R. B. Noel, Arzneim.-Forsch. 19, 1246 (1969).
Properties
Crystals from benzene, mp 105° (Morren); also reported as mp 108° (Bourdais). LD50 in rats (mg/kg): 200 i.v., 750 orally (Morren).Derivative
S-Form.Nomenclature
CAS number: 99291-24-4
Levodropropizine; Danka (Mediolanum); Levotuss (Dompé); Rapitux (De Angeli). Properties
White solid from acetone, mp 98-100°. [α]D25 -10° (c = 1.0 in ethanol). LD50 in mice, rats (mg/kg): 1287.2, 886.6 orally; 408.0, 401.3 i.p. (Borsa).Derivative
R-Form.Properties
Crystals from acetone, mp 104-105°. [α]D25 +9.7° (c = 1.0 in ethanol). LD50 in mice, rats (mg/kg): 871.7, 721.3 orally; 319.2, 363.4 i.p. (Borsa).Therapeutic Category
Antitussive.
Keywords
Antitussive