| Ascomycin Basic information |
| Product Name: | Ascomycin |
| Synonyms: | ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS;ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS VAR ASCOMYCETICUS;FR-900520;FK-520;IMMUNOMYCIN;AAG;ASCOMYCIN (IMMUNOMYCIN, FR-900520) \ INH IBITS CALCINEURIN (PP2B);(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-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 |
| CAS: | 11011-38-4 |
| MF: | C43H69NO12 |
| MW: | 792.01 |
| EINECS: | 658-052-0 |
| Product Categories: | API;Immunosuppressant |
| Mol File: | 11011-38-4.mol |
| Ascomycin Chemical Properties |
| Melting point | 158 - 161°C |
| storage temp. | -20°C |
| solubility | Soluble in DMSO (up to 50 mg/ml), or in Ethanol (up to 50 mg/ml with warming). |
| form | White crystalline solid |
| color | White |
| Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Safety Information |
| RTECS | CI7570000 |
| MSDS Information |
| Ascomycin Usage And Synthesis |
| Description | Ascomycin (11011-38-4) is an analog of FK-506 (Cat.# 10-1103). Potent immunosuppressant1. Binds to FKBP122 and inhibits calcineurin and NFAT. Ascomycin displays anti-inflammatory effects in skin diseases3. Cell permeable and active in vivo. |
| Uses | A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases. |
| General Description | An ethyl analog of FK506 with similar immunosuppressant properties. Acts by binding to immunophilins. Inhibits the synthesis of Th-1 and Th-2 type cytokines in target cells. |
| Biochem/physiol Actions | Product does not compete with ATP. |
| Enzyme inhibitor | This antifungal antibiotic (FW = 792.02 g/mol; CAS 104987-12-4; Solubility: 50 mM in DMSO), also known as FK520, isolated from Streptomyces hygroscopicus, is also a powerful immunosuppressant. Note that ascomycin is a structural analogue of tacrolimus (or FK506) and, as such, operates by a similar mechanism of action (See Tacrolimus). Ascomycin inhibits allogenic T-lymphocyte proliferation and calcineurin phosphatase activity. |
| References | 1) Hatanaka et al. (1988), FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physio-chemical and biological characteristics; J. Antibiot. (Tokyo), 41 1592 2) Petros et al. (1991), NMR studies of an FK506 analogue [U-13C]ascomycin, bound to FKBP: conformation and regions of ascomycin involved in binding; J. Med. Chem., 34 2925 3) Mollison et al. (1999), A macrolactam inhibitor of T helper type 1 and T helper type 2 cytokine biosynthesis for topical treatment of inflammatory skin diseases; J. Invest. Dermatol., 112 729 |
| Ascomycin Preparation Products And Raw materials |
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