| Revision as of 14:03, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CAS_number').← Previous edit |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| IUPAC_name = (3''S'',​4''R'',​5''S'',​8''R'',​9''Z'',​12''S'',​14''S'',​15''R'',​16''S'',​18''R'',​19''R'',​26a''S'')-​8-​ethyl-​5,​19-​dihydroxy-​3-​{(''E'')-​2-​-​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-​3''H''-​15,​19-​epoxypyrido​oxazacyclotriclosine-1,​7,​20,​21(23''H'')-​tetrone |
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| verifiedrevid = 457820106 |
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| IUPAC_name = (3''S'',4''R'',5''S'',8''R'',9''Z'',12''S'',14''S'',15''R'',16''S'',18''R'',19''R'',26a''S'')-8-ethyl-5,19-dihydroxy-3-{(''E'')-2--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-3''H''-15,19-epoxypyridooxazacyclotricosine-1,7,20,21(23''H'')-tetrone |
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| image = Ascomycin structure.png |
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| image = Ascomycin structure.png |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 11011-38-4 --> |
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| CAS_number = 104987-12-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = AUF4U5NSJK |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 5282071 |
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| PubChem = 5282071 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4445297 |
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| ChemSpiderID = 4445297 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 29582 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 8597 |
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| ChEMBL = 8597 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=43 | H=69 | N=1 | O=12 |
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| C=43 | H=69 | N=1 | O=12 |
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| molecular_weight = 792.01 g/mol |
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| smiles = O=C3C(=O)N1CCCC1C(=O)O(C(=C/2CC(O)(OC)C2)/C)(C)(O)CC(=O)(/C=C(\C(C(OC)4O3(O)(C)C4OC)C)C)CC |
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| smiles = O=C3C(=O)N1CCCC1C(=O)O(C(=C/2CC(O)(OC)C2)/C)(C)(O)CC(=O)(/C=C(\C(C(OC)4O3(O)(C)C4OC)C)C)CC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZDQSOHOQTUFQEM-NURRSENYSA-N |
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| StdInChIKey = ZDQSOHOQTUFQEM-NURRSENYSA-N |
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| synonyms = <small>17-ethyl-1,14-dihydroxy-12--23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclooctacos-18-ene-2,3,10,16-tetraone</small> |
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| synonyms = <small>17-ethyl-1,14-dihydroxy-12--23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclooctacos-18-ene-2,3,10,16-tetraone</small> |
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}} |
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}} |
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'''Ascomycin''', also called Immunomycin, FR-900520, FK520, is an ] analog of ] (FK506) with strong immunosuppressant properties. It can be used to treat ] and ], and can help prevent rejection after an ]. |
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'''Ascomycin''', also called Immunomycin, FR-900520, FK520, is an ] analog of ] (FK506) with strong immunosuppressant properties. It has been researched for the treatment of ] and ], and to prevent rejection after an ].<ref>{{cite journal | vauthors = Andexer JN, Kendrew SG, Nur-e-Alam M, Lazos O, Foster TA, Zimmermann AS, Warneck TD, Suthar D, Coates NJ, Koehn FE, Skotnicki JS, Carter GT, Gregory MA, Martin CJ, Moss SJ, Leadlay PF, Wilkinson B | display-authors = 6 | title = Biosynthesis of the immunosuppressants FK506, FK520, and rapamycin involves a previously undescribed family of enzymes acting on chorismate | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 108 | issue = 12 | pages = 4776–4781 | date = March 2011 | pmid = 21383123 | pmc = 3064383 | doi = 10.1073/pnas.1015773108 | doi-access = free }}</ref> |
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Ascomycin acts by binding to ], especially ]. It appears that Ascomycin inhibits the production of Th1 (interferon- and IL-2) and Th2 (IL-4 and IL-10) ]s. Additionally, ascomycin preferentially inhibits the activation of ], an important cellular component of the atopic response. Ascomycin produces a more selective ] effect in that it inhibits the elicitation phase of ] but does not impair the primary immune response when administered systemically. |
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Ascomycin acts by binding to ], especially ]. It appears that Ascomycin inhibits the production of Th1 (interferon- and IL-2) and Th2 (IL-4 and IL-10) ]s. Additionally, ascomycin preferentially inhibits the activation of ], an important cellular component of the atopic response. Ascomycin produces a more selective ] effect in that it inhibits the elicitation phase of ] but does not impair the primary immune response when administered systemically.<ref>{{cite journal | vauthors = Paul C, Graeber M, Stuetz A | title = Ascomycins: promising agents for the treatment of inflammatory skin diseases | journal = Expert Opinion on Investigational Drugs | volume = 9 | issue = 1 | pages = 69–77 | date = January 2000 | pmid = 11060661 | doi = 10.1517/13543784.9.1.69 | s2cid = 19730971 }}</ref> |
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Ascomycin is produced by the ] of certain strains of '']''.<ref>{{cite journal | vauthors = Yu Z, Lv H, Wu Y, Wei T, Yang S, Ju D, Chen S | title = Enhancement of FK520 production in Streptomyces hygroscopicus by combining traditional mutagenesis with metabolic engineering | journal = Applied Microbiology and Biotechnology | volume = 103 | issue = 23-24 | pages = 9593–9606 | date = December 2019 | pmid = 31713669 | doi = 10.1007/s00253-019-10192-8 | s2cid = 207955563 }}</ref> |
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Ascomycin is produced by the ] of ] hygroscopicus. |
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== In fiction == |
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Ascomycin is also the name of a fictional "antiagathic" (anti-aging) drug in ]'s future history '']''.<ref>{{cite web |title=Anti-agathic drugs |url=http://www.technovelgy.com/ct/content.asp?Bnum=1480 |website=Technovelgy.com |access-date=15 June 2022}}</ref> and in its component novel ''They Shall Have Stars.'' |
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== Related compounds == |
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== Related compounds == |
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== References == |
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== References == |
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{{Reflist}} |
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*Griffiths CE. Ascomycin: an advance in the management of atopic dermatitis. Br J Dermatol. 2001. Apr;144(4):679-81. |
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*Kawai, M., et al., Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues. FEBS Lett. 1993. 316(2): 107-13. |
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*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. |
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*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. |
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*Morisaki M, Arai T., Related Articles, Identity of immunosuppressant FR-900520 with ascomycin. J Antibiot (Tokyo). 1992. Jan;45(1):126-8. |
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*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. |
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== Further reading == |
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==External links== |
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{{refbegin}} |
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* By Jane Schwanke, WebMD Medical News March 17, 2000 (San Francisco) |
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* {{cite journal | vauthors = Griffiths CE | title = Ascomycin: an advance in the management of atopic dermatitis | journal = The British Journal of Dermatology | volume = 144 | issue = 4 | pages = 679–681 | date = April 2001 | pmid = 11298524 | doi = 10.1046/j.1365-2133.2001.144004679.x | s2cid = 46503687 }} |
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* {{cite journal | vauthors = Kawai M, Lane BC, Hsieh GC, Mollison KW, Carter GW, Luly JR | title = Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues | journal = FEBS Letters | volume = 316 | issue = 2 | pages = 107–113 | date = January 1993 | pmid = 7678400 | doi = 10.1016/0014-5793(93)81196-7 | s2cid = 24298979 | doi-access = free }} |
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* {{cite journal | vauthors = Zuberbier T, Chong SU, Grunow K, Guhl S, Welker P, Grassberger M, Henz BM | title = The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils | journal = The Journal of Allergy and Clinical Immunology | volume = 108 | issue = 2 | pages = 275–280 | date = August 2001 | pmid = 11496246 | doi = 10.1067/mai.2001.116865 | doi-access = free }} |
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* {{cite journal | vauthors = Mollison KW, Fey TA, Krause RA, Thomas VA, Mehta AP, Luly JR | title = Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation | journal = Annals of the New York Academy of Sciences | volume = 685 | issue = | pages = 55–57 | date = June 1993 | pmid = 7689812 | doi = 10.1111/j.1749-6632.1993.tb35851.x | s2cid = 28990806 }} |
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* {{cite journal | vauthors = Paul C, Graeber M, Stuetz A | title = Ascomycins: promising agents for the treatment of inflammatory skin diseases | journal = Expert Opinion on Investigational Drugs | volume = 9 | issue = 1 | pages = 69–77 | date = January 2000 | pmid = 11060661 | doi = 10.1517/13543784.9.1.69 | s2cid = 19730971 }} |
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{{refend}} |
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== External links == |
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* By Jane Schwanke, WebMD Medical News March 17, 2000 (San Francisco) |
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