7705. Pramipexole
Nomenclature
CAS number: 104632-26-0
(6S)-4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine; (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole. C10H17N3S; mol wt 211.33.
C 56.83%, H 8.11%, N 19.88%, S 15.17%.
Description and references
Dopamine agonist active at d3 and d2 receptor subtypes. Prepn of racemate: G. Griss et al., EP 186087; eidem, US 4886812 (1986, 1989 both to Thomae); of enantiomers: C. S. Schneider, J. Mierau, J. Med. Chem. 30, 494 (1987). Pharmacology: J. Mierau, G. Schingnitz, Eur. J. Pharmacol. 215, 161 (1992). Clinical safety and pharmacodynamics: J. C. Schilling et al., Clin. Pharmacol. Ther. 51, 541 (1992). Clinical trial in Parkinson's disease: K. Kieburtz et al., J. Am. Med. Assoc. 278, 125 (1997). Review of clinical trials in restless legs syndrome: C. A. Kushida, Expert Opin. Pharmacother. 7, 441-451 (2006).
Derivative
Dihydrochloride monohydrate.Nomenclature
CAS number: 191217-81-9;
104632-25-9
(dihydrochloride)
SND-919; Mirapex (Boehringer, Ing.); Mirapexin (Boehringer, Ing.); Sifrol (Boehringer, Ing.). C10H17N3S.2HCl.H2O; mol wt 302.26.
C 39.74%, H 7.00%, N 13.90%, S 10.61%, Cl 23.46%, O 5.29%.
Properties
White to off-white powder, mp 296-301° (dec). [α]D20 -67.2° (c = 1 in methanol). Soly: water >20%; methanol ~8%; ethanol ~0.5%. Practically insol in dichloromethane.Therapeutic Category
Antiparkinsonian. In treatment of restless legs syndrome.
Keywords
Antiparkinsonian; Dopamine Receptor Agonist