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| | Ascomycin Basic information |
| Product Name: | Ascomycin | | Synonyms: | 15,19-Epoxy-3H-pyrido(2,1-C)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26A-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetram;C058028;AscoMycin solution;L 683590, FR 900520, IMMunoMycin, FK 520, WS 7238A, NSC 106410;Ascomycin:Tacrolimus Desmethylene Impurit;Tacrolimus USP RC A;Tacrolimus Imprity 6;Ascomycin:Tacrolimus Desmethylene Impurity | | CAS: | 104987-12-4 | | MF: | C43H69NO12 | | MW: | 792.01 | | EINECS: | 600-627-5 | | Product Categories: | antibiotic;Inhibitors;Intermediates & Fine Chemicals;Inhibits an EnzymeAntibiotics;Mechanism of Action;Spectrum of Activity;Pharmaceuticals;Macrolactams;Antibiotics;Antibiotics A to;Antibiotics A-FAntibiotics;Antibiotics by Application;AntifungalAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Chemical Structure Class | | Mol File: | 104987-12-4.mol |  |
| | Ascomycin Chemical Properties |
| Melting point | 153-157°C | | Boiling point | 868℃ | | density | 1.19±0.1 g/cm3(Predicted) | | Fp | >110°(230°F) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | ≥38.9 mg/mL in DMSO; insoluble in H2O; ≥98.6 mg/mL in EtOH | | form | Powder | | pka | 9.97±0.70(Predicted) | | Water Solubility | Soluble in DMSO at 65mg/ml; soluble in ethanol at 50mg/m; with warming. Very poorly soluble in water | | InChIKey | ZDQSOHOQTUFQEM-AMASXYNMSA-N |
| Hazard Codes | Xn,F | | Risk Statements | 20/21/22-36-11 | | Safety Statements | 36/37-16 | | RIDADR | UN 1648 3 / PGII | | WGK Germany | 3 | | RTECS | KD4185000 | | F | 10 | | HS Code | 29419090 |
| | Ascomycin Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases | | Uses | Ascomycin is a macrocyclic lactone closely related to tacrolimus and rapamycin. Ascomycin is isolated from several species of Streptomyces and was first reported in 1988. Ascomycin exhibits limited, potent antifungal activity but has found considerable utility as an immunosuppressant. | | Uses | Everolimus is a semi-synthetic macrocyclic lactone prepared from rapamycin by selective alkylation of the 42-hydroxy group with a silyl-protected hydroxyethyl triflate moiety, followed by addition of an ethylhydroxy moiety to provide greater stability and bioavailability. Like all tacrolimus analogues, everolimus binds to receptor protein, FKBP12. The complex then binds to mTOR preventing it from interacting with target proteins. Everolimus is extensively cited in the literature with over 2,000 citations. | | Definition | ChEBI: A macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties. | | Biological Activity | ascomycin (fk 520, fr900520) is a novel neutral macrolide immunosuppressant, isolated from the cultured broth of streptomyces hygroscopicus subsp. yakushimaensis no. 7238. | | in vitro | ascomycin (fk 520, fr900520) suppressed lymphocyte reaction in a dose dependent fashion. ascomycin was non-toxic at concentrations less than 3,200 nm, at which the percent inhibition was 18.9%. ascomycin showed antifungal activity against aspergillus fumigatus ifo 5840. ascomycin had no inhibitory effect on bacteria or yeast at 100 μg/ml [1]. | | in vivo | ascomycin was dose-dependently effective and clearly prolonged skin allograft survival at 3.2 mg/kg or more, though all skin allografts were rejected within 7 days in rats treated intramuscularly with olive oil. ascomycin, dissolved in olive oil, showed no adverse effect when administered intraperitoneally to ddy mice (male, 8 weeks old) at 100 mg/kg [1]. | | target | peptidyl-prolyl cis-trans isomerase | | storage | -20°C | | references | [1] hatanaka h, kino t, miyata s, inamura n, kuroda a, goto t, tanaka h, okuhara m. fr-900520 and fr-900523, novel immunosuppressants isolated from a streptomyces. ii. fermentation, isolation and physico-chemical and biological characteristics. j antibiot (tokyo). 1988;41(11):1592-601. |
| | Ascomycin Preparation Products And Raw materials |
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