7429. Pimecrolimus
Nomenclature
CAS number: 137071-32-0
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-3-[(1E)-2-[(1R,3R,4S)-4-Chloro-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone; 33-epi-chloro-33-desoxyascomycin; SDZ-ASM-981; Elidel (Novartis). C43H68ClNO11; mol wt 810.45.
C 63.73%, H 8.46%, Cl 4.37%, N 1.73%, O 21.72%.
Description and references
Macrolactam ascomycin derivative. Specific calcineurin inhibitor that blocks production of pro-inflammatory cytokines by T cells and mast cells. Prepn: K. Baumann, G. Emmer, EP 427680 (1991 to Sandoz); eidem, US 5912238 (1999 to Novartis). In vitro pharmacology: M. Grassberger et al., Br. J. Dermatol. 141, 264 (1999). Clinical evaluation in psoriasis: U. Mrowietz et al., ibid. 139, 992 (1998); in contact dermatitis: C. Queille-Roussel et al., Contact Dermatitis 42, 349 (2000). Review of clinical experience in inflammatory skin conditions: U. Wollina et al., Expert Opin. Pharmacother. 7, 1967-1975 (2006).
Properties
White to off-white fine crystalline powder. Highly lipophilic. Sol in methanol and ethanol. Insol in water.Therapeutic Category
Immunosuppressant; dermatological in treatment of atopic eczema.
Keywords
Immunosuppressant; Antieczematic; Calcineurin Inhibitor