アスコマイシン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/20 09:19:02」(JST)
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Ascomycin
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| Systematic (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]oxazacyclotriclosine-1,7,20,21(23H)-tetrone |
| Clinical data |
| Pregnancy cat. |
? |
| Legal status |
? |
| Identifiers |
| CAS number |
11011-38-4 N |
| ATC code |
None |
| PubChem |
CID 5282071 |
| ChemSpider |
4445297 Y |
| ChEMBL |
CHEMBL8597 Y |
| Synonyms |
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 |
| Chemical data |
| Formula |
C43H69NO12 |
| Mol. mass |
792.01 g/mol |
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
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N (what is this?) (verify)
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Ascomycin, also called Immunomycin, FR-900520, FK520, is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. It can be used to treat autoimmune diseases and skin diseases, and can help 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 Streptomyces hygroscopicus.
Contents
- 1 In fiction
- 2 Related compounds
- 3 References
- 4 External links
In fiction[edit source | edit]
Ascomycin is also the name of a fictional "antiagathic" (anti-aging) drug in James Blish's future history Cities in Flight.
Related compounds[edit source | edit]
Tacrolimus, Pimecrolimus
References[edit source | edit]
- Griffiths CE. Ascomycin: an advance in the management of atopic dermatitis. Br J Dermatol. 2001. Apr;144(4):679-81.
- Kawai, M., et al., Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues. FEBS Lett. 1993. 316(2): 107-13.
- Zuberbier T, Chong SU, Grunow K, Guhl S, Welker P, Grassberger M, Henz BM. The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils. J Allergy Clin Immunol. 2001. Aug;108(2): 275-80.
- Mollison KW, Fey TA, Krause RA, Thomas VA, Mehta AP, Luly JR. Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation. Ann N Y Acad Sci. 1993. Jun 23; 685:55-7.
- Morisaki M, Arai T., Related Articles, Identity of immunosuppressant FR-900520 with ascomycin. J Antibiot (Tokyo). 1992. Jan;45(1):126-8.
- Paul C., Graeber M, Stuetz A., Ascomycins: promising agents for the treatment of inflammatory skin diseases. Expert Opin Investig Drugs. 2000. Jan;9(1):69-77.#Mrowietz U., Macrolide immunosuppressants. Eur J Dermatol. 1999. Jul-Aug;9(5):346-51.
External links[edit source | edit]
- Exciting New Eczema Treatment Expected This Year By Jane Schwanke, WebMD Medical News March 17, 2000 (San Francisco)
UpToDate Contents
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English Journal
- Integration of parallel 13 C-labeling experiments and in silico pathway analysis for enhanced production of ascomycin.
- Qi H1,2, Lv M1,2, Song K1,2, Wen J1,2.
- Biotechnology and bioengineering.Biotechnol Bioeng.2017 May;114(5):1036-1044. doi: 10.1002/bit.26223. Epub 2016 Nov 29.
- PMID 27869289
- Engineering of the LysR family transcriptional regulator FkbR1 and its target gene to improve ascomycin production.
- Song K1,2, Wei L1,2, Liu J1,2, Wang J1,2, Qi H1,2, Wen J3,4.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2017 Mar 27. doi: 10.1007/s00253-017-8242-4. [Epub ahead of print]
- PMID 28349163
- Development and validation of a liquid chromatography-mass spectrometric assay for simultaneous determination of tacrolimus and 13-O-desmethyl tacrolimus in rat kidney tissue.
- Kirresh T1, Tuteja S1, Russo D2, Brophy PD2, Murry DJ3.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2017 Mar 20;136:32-37. doi: 10.1016/j.jpba.2016.12.034. Epub 2016 Dec 29.
- PMID 28063333
Japanese Journal
- Quantitative Determination of Cyclosporine in Human Whole Blood by Ultra-Performance Liquid Chromatography with Triple Quadrupole Tandem Mass Spectrometry
- Evaluation, synthesis and characterization of tacrolimus impurities
- LC/ESI-MS/MSを用いた免疫抑制剤シロリムスの血中濃度測定
Related Links
- Cluster information : Ascomycin Compound Original source Module Reference Data download Compound Entry name Ascomycin Synonym FK520 PKS Type PKS-NRPS hybrid Classification Other Macrocyclic Lactone Starter Unit 4 ...
- Ascomycin (also known as Immunomycin) is an analog of tacrolimus with immunosuppressive, neurotrophic and antifungal activities. Ascomycin can be used to prevent rejection after an organ transplant, and to treat autoimmune ...
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