2034. Cevimeline
Nomenclature
CAS number: 107233-08-9
(2′R,3R)-rel-2′-Methylspiro[1-azabicyclo[2.2.2]octane-3,5′-[1,3]oxathiolane]; (±)-cis-2-methylspiro[1,3-oxathiolane-5,3′-quinuclidine]. C10H17NOS; mol wt 199.31.
C 60.26%, H 8.60%, N 7.03%, O 8.03%, S 16.09%.
Description and references
Muscarinic M1 and M3 receptor agonist. Prepn: A. Fisher et al., JP Kokai 61 280497; eidem, US 4855290; (1986, 1989 both to State of Israel). Improved process: K. Hayashi et al., US 5571918 (1996 to Ishihara Sangyo Kaisha). Sialogogic effect in animals: H. Masunaga et al., Eur. J. Pharmacol. 339, 1 (1997). General pharmacology: H. Arisawa et al., Arzneim.-Forsch. 52, 14, 81 (2002). Clinical experience in Sj"ogren's syndrome dry eye: M. Ono et al., Am. J. Ophthalmol. 138, 6 (2004); in dry mouth: K. Suzuki et al., Pharmacology 74, 100 (2005). Review of clinical pharmacokinetics and efficacy in Sj"ogren's syndrome: H. Yasuda, H. Niki, Clin. Drug Invest. 22, 67-73 (2002).
Derivative
Hydrochloride hemihydrate.Nomenclature
CAS number: 153504-70-2;
107220-28-0
(anhydrous)
AF-102B; SNI-2011; Evoxac (Daiichi). C10H17NOS.HCl. 1/2 H2O; mol wt 244.78.
C 49.07%, H 7.82%, N 5.72%, O 9.80%, S 13.10%, Cl 14.48%.
Properties
White to off white crystalline powder, mp 201-203°. Freely sol in alcohol, chloroform; very sol in water. Virtually insol in ether.Therapeutic Category
Sialagogue.
Keywords
Sialagogue