Chemistry:Ascomycin

Short description: Chemical compound

Ascomycin

Clinical data
Other names	17-ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone
ATC code	none
Identifiers
IUPAC name (3S,4R,5S,8R,9Z,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylvinyl}-14,16-dimethoxy-4,10,12,18-tetramethyl-4,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-heptadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(23H)-tetrone
CAS Number	104987-12-4 Y
PubChem CID	5282071
ChemSpider	4445297 Y
UNII	AUF4U5NSJK
ChEBI	CHEBI:29582 N
ChEMBL	ChEMBL8597 Y
Chemical and physical data
Formula	C43H69NO12
Molar mass	792.020 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C3C(=O)N1CCCC[C@H]1C(=O)O[C@H](C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(\C[C@@H](C[C@H](OC)[C@H]4O[C@]3(O)[C@H](C)C[C@@H]4OC)C)C)CC
InChI InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1 Y Key:ZDQSOHOQTUFQEM-NURRSENYSA-N Y
NY (what is this?)  (verify)

Ascomycin, also called Immunomycin, FR-900520, FK520, is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. It has been researched for the treatment of autoimmune diseases and skin diseases, and to prevent rejection after an organ transplant.

Ascomycin acts by binding to immunophilins, especially macrophilin-12. It appears that Ascomycin inhibits the production of Th1 (interferon- and IL-2) and Th2 (IL-4 and IL-10) cytokines. Additionally, ascomycin preferentially inhibits the activation of mast cells, an important cellular component of the atopic response. Ascomycin produces a more selective immunomodulatory effect in that it inhibits the elicitation phase of allergic contact dermatitis but does not impair the primary immune response when administered systemically.

Ascomycin is produced by the fermentation of certain strains of Streptomyces hygroscopicus.

In fiction

Ascomycin is also the name of a fictional "antiagathic" (anti-aging) drug in James Blish's future history Cities in Flight. and also They shall have stars.

Related compounds

Tacrolimus, Pimecrolimus

Further reading

• "Ascomycin: an advance in the management of atopic dermatitis". The British Journal of Dermatology 144 (4): 679–681. April 2001. doi:10.1046/j.1365-2133.2001.144004679.x. PMID 11298524. 
• "Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues". FEBS Letters 316 (2): 107–113. January 1993. doi:10.1016/0014-5793(93)81196-7. PMID 7678400. 
• "The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils". The Journal of Allergy and Clinical Immunology 108 (2): 275–280. August 2001. doi:10.1067/mai.2001.116865. PMID 11496246. 
• "Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation". Annals of the New York Academy of Sciences 685: 55–57. June 1993. doi:10.1111/j.1749-6632.1993.tb35851.x. PMID 7689812. 
• "Ascomycins: promising agents for the treatment of inflammatory skin diseases". Expert Opinion on Investigational Drugs 9 (1): 69–77. January 2000. doi:10.1517/13543784.9.1.69. PMID 11060661. 

External links

• Exciting New Eczema Treatment Expected This Year By Jane Schwanke, WebMD Medical News March 17, 2000 (San Francisco)