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Ascomycin is an ethyl analog of FK506 that was initially produced by species of Streptomyces. Ascomycin binds FK506 binding protein 12 and the resulting complex inhibits calcineurin/protein phosphatase 2B (PP2B), altering peptidyl-prolyl isomerase activity of the enzyme. Ascomycin exhibits immunosuppressive, anti-inflammatory, and anticonvulsant activities. Clinically, ascomycin is used to treat organ transplant rejection and inflammatory skin diseases.
| Cas No. | 104987-12-4 |
|---|---|
| Purity | ≥98% |
| Formula | C43H69NO12 |
| Formula Wt. | 792.01 |
| IUPAC Name | (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone |
| Synonym | Immunomycin |
| Melting Point | 162-163°C |
| Solubility | Soluble in DMSO |
| Appearance | White Powder |
| Store Temp | 4°C |
|---|---|
| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Liu F, Wang YQ, Meng L, et al. FK506-binding protein 12 ligands: a patent review. Expert Opin Ther Pat. 2013 Nov;23(11):1435-49. PMID: 23957229.
Sierra-Paredes G, Sierra-Marcuño G. Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants. CNS Neurosci Ther. 2008 Spring;14(1):36-46. PMID: 18482098.
Pahl A, Keller U. FK-506-binding proteins from streptomycetes producing immunosuppressive macrolactones of the FK-506 type. J Bacteriol. 1992 Sep;174(18):5888-94. PMID: 1381710.