Chemistry:Ascomycin

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Short description: Chemical compound
Ascomycin
Ascomycin structure.png
Clinical data
Other names17-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
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC43H69NO12
Molar mass792.020 g·mol−1
3D model (JSmol)
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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.[1]

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.[2]

Ascomycin is produced by the fermentation of certain strains of Streptomyces hygroscopicus.[3]

In fiction

Ascomycin is also the name of a fictional "antiagathic" (anti-aging) drug in James Blish's future history Cities in Flight.[4] and also They shall have stars.

Related compounds

Tacrolimus, Pimecrolimus

References

  1. "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 108 (12): 4776–4781. March 2011. doi:10.1073/pnas.1015773108. PMID 21383123. 
  2. "Ascomycins: promising agents for the treatment of inflammatory skin diseases". Expert Opinion on Investigational Drugs 9 (1): 69–77. January 2000. doi:10.1517/13543784.9.1.69. PMID 11060661. 
  3. "Enhancement of FK520 production in Streptomyces hygroscopicus by combining traditional mutagenesis with metabolic engineering". Applied Microbiology and Biotechnology 103 (23-24): 9593–9606. December 2019. doi:10.1007/s00253-019-10192-8. PMID 31713669. 
  4. "Anti-agathic drugs". http://www.technovelgy.com/ct/content.asp?Bnum=1480. 

Further reading

  • "Ascomycin: an advance in the management of atopic dermatitis". The British Journal of Dermatology 144 (4): 679–681. April 2001. doi:10.1046/j.1365-2133.2001.144004679.x. PMID 11298524. 
  • "Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues". FEBS Letters 316 (2): 107–113. January 1993. doi:10.1016/0014-5793(93)81196-7. PMID 7678400. 
  • "The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils". The Journal of Allergy and Clinical Immunology 108 (2): 275–280. August 2001. doi:10.1067/mai.2001.116865. PMID 11496246. 
  • "Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation". Annals of the New York Academy of Sciences 685: 55–57. June 1993. doi:10.1111/j.1749-6632.1993.tb35851.x. PMID 7689812. 
  • "Ascomycins: promising agents for the treatment of inflammatory skin diseases". Expert Opinion on Investigational Drugs 9 (1): 69–77. January 2000. doi:10.1517/13543784.9.1.69. PMID 11060661. 

External links