Chemistry:Pecilocin

From HandWiki

Pecilocin (brand name Variotin) is a pyrrolidine anti-fungal.[1] It is produced by Paecilomyces varioti Bainer var. antibioticus and was first isolated by Setsuo Takeuchi in 1959.[2] Later, it was established that other fungi also produce this compound, which include Aspergillus candidus and Aspergillus montenegroi.[3]

Uses

Pecilocin is indicated for topical treatment of fungal infections of skin and its adnexa,[4] i.e.:

Antifungal spectrum

Pecilocin is a fungistatic and has activity against genera Blastomyces, Cryptococcus, Epidermophyton, Microsporum and Trichophyton (with MIC less or equal to 0,25 μg/ml).[5] C. albicans is inherently resistant.

Adverse effects

Common adverse effects associated with pecilocin include: skin irritation (observed in 2-6.5% of patients), as well as contact dermatitis. Some patients might exhibit allergy to pecilocin.[6]

Biosynthesis

A radioactive carbon study of pecilocin biosynthetic pathway conducted by Nobuo Tanaka showed it is synthesised from acetic acid, glutamate and L-methionine.[5]

References

  1. "Pecilocin | C17H25NO3 | ChemSpider". http://www.chemspider.com/Chemical-Structure.4445371.html. 
  2. "Studies on variotin, a new antifungal antibiotic. I. Preparations and properties of variotin". The Journal of Antibiotics 12: 195–200. September 1959. PMID 13855011. 
  3. "Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites". Frontiers in Microbiology 12. 2021-12-23. doi:10.3389/fmicb.2021.804333. PMID 35003037. 
  4. Leki współczesnej terapii (Wydanie XXII ed.). Warszawa: Medical Tribune Polska. 2019. ISBN 978-83-951310-6-6. 
  5. 5.0 5.1 (in en) Biosynthesis. Berlin, Heidelberg: Springer Berlin Heidelberg. 1967. doi:10.1007/978-3-662-38441-1. ISBN 978-3-662-37650-8. https://link.springer.com/10.1007/978-3-662-38441-1. 
  6. "Antifungal azoles and other antifungal drugs for topical use" (in en). Meyler's Side Effects of Drugs. Elsevier. 2016. pp. 602–605. doi:10.1016/b978-0-444-53717-1.00312-7. ISBN 978-0-444-53716-4. https://linkinghub.elsevier.com/retrieve/pii/B9780444537171003127. Retrieved 2025-02-08.