Ascomycin

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Chemical compound

title: "Ascomycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["immunosuppressants"] description: "Chemical compound" topic_path: "general/immunosuppressants" source: "https://en.wikipedia.org/wiki/Ascomycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | verifiedrevid = 457820106 | 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]oxazacyclotricosine-1,7,20,21(23H)-tetrone | image = Ascomycin structure.png | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 104987-12-4 | UNII_Ref = | UNII = AUF4U5NSJK | ATC_prefix = none | ATC_suffix = | PubChem = 5282071 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 4445297 | ChEBI_Ref = | ChEBI = 29582 | ChEMBL_Ref = | ChEMBL = 8597

| C=43 | H=69 | N=1 | O=12 | smiles = O=C3C(=O)N1CCCC[C@H]1C(=O)OC@HC@HC@@HCC(=O)C@@HCC | StdInChI_Ref = | 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 | StdInChIKey_Ref = | StdInChIKey = ZDQSOHOQTUFQEM-NURRSENYSA-N | 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

Ascomycin, also called Immunomycin, FR-900520, FK520, is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. It has been researched for the treatment of autoimmune diseases and skin diseases, and to 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 certain strains of Streptomyces hygroscopicus.

In fiction

Ascomycin is also the name of a fictional "antiagathic" (anti-aging) drug in James Blish's future history Cities in Flight. and in its component novel They Shall Have Stars.

Related compounds

Tacrolimus, Pimecrolimus

References

References

  1. (March 2011). "Biosynthesis of the immunosuppressants FK506, FK520, and rapamycin involves a previously undescribed family of enzymes acting on chorismate". Proceedings of the National Academy of Sciences of the United States of America.
  2. (January 2000). "Ascomycins: promising agents for the treatment of inflammatory skin diseases". Expert Opinion on Investigational Drugs.
  3. (December 2019). "Enhancement of FK520 production in Streptomyces hygroscopicus by combining traditional mutagenesis with metabolic engineering". Applied Microbiology and Biotechnology.
  4. "Anti-agathic drugs".

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immunosuppressants