10253. Rotigotine

Nomenclature

CAS number: 99755-59-6
(6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenol; ()-2-(N-propyl-N-2-thienylethylamino)-5-hydroxytetralin; ()-5-hydroxy-2[N-n-propyl-N-2-(2-thienyl)ethylamino]tetralin; N-0923; SPM-962; Neupro (Schwarz).
C19H25NOS; mol wt 315.47.
C 72.34%, H 7.99%, N 4.44%, O 5.07%, S 10.16%.

Description and references

Non-ergot dopamine receptor agonist. Prepn and activity of enantiomers: W. Timmerman et al., Eur. J. Pharmacol. 166, 1 (1989) DOI PubMed. Improved synthesis: G. Minaskanian, K. Rippel, US 6372920 (2002 to Aderis). Clinical trial of transdermal formulation in early Parkinson's disease: R. L. Watts et al., Neurology 68, 272 (2007) DOI PubMed. Review of pharmacology and clinical experience of transdermal formulation in Parkinson's disease: Y. Naidu, K. Ray Chaudhuri, Expert Opin. Drug Deliv. 4, 111-118 (2007) DOI PubMed; and in restless legs syndrome: M. Y. Splinter, Ann. Pharmacother. 41, 285-295 (2007) DOI PubMed.

Chemical structure

Properties

White to off-white powder. Sensitive to oxidation. Non-hygroscopic. Lipophilic and poorly sol in water at neutral pH; soly increases at more acidic pH.

Derivative

Hydrochloride.

Nomenclature

CAS number: 125572-93-2
C19H25NOS.HCl; mol wt 351.93.
C 64.84%, H 7.45%, N 3.98%, O 4.55%, S 9.11%, Cl 10.07%.

Description and references

Determn of enantiomeric purity by chiral HPLC: D. T. Witte et al., Chirality 4, 62 (1992) DOI. GC/MS determn in plasma: P. A. Zavitsanos et al., Rapid Commun. Mass Spectrom. 7, 1145 (1993) DOI PubMed.

Properties

White crystalline solid. [α]57825 55.79° (c = 0.99 in MeOH).

Derivative

±-Form.

Nomenclature

CAS number: 92206-54-7
N-0437.

Description and references

Prepn: A. S. Horn, US 4564628 (1986 to Nelson).

Therapeutic Category

Antiparkinsonian.

Keywords

Dopamine Receptor Agonist