Pecilocin

Pecilocin
Names
Preferred IUPAC name
1-[(2E,4E,6E,8R)-8-Hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one
Other names
Latin: pecilocinum
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.039.182 Edit this at Wikidata
EC Number
  • 243-116-9
KEGG
UNII
  • InChI=1S/C17H25NO3/c1-3-4-9-15(19)13-14(2)8-5-6-10-16(20)18-12-7-11-17(18)21/h5-6,8,10,13,15,19H,3-4,7,9,11-12H2,1-2H3/b8-5+,10-6+,14-13+/t15-/m1/s1 X markN
    Key: ZYPGADGCNXOUJP-CXVPHVKISA-N X markN
  • InChI=1/C17H25NO3/c1-3-4-9-15(19)13-14(2)8-5-6-10-16(20)18-12-7-11-17(18)21/h5-6,8,10,13,15,19H,3-4,7,9,11-12H2,1-2H3/b8-5+,10-6+,14-13+/t15-/m1/s1
    Key: ZYPGADGCNXOUJP-CXVPHVKIBE
  • CCCC[C@H](/C=C(\C)/C=C/C=C/C(=O)N1CCCC1=O)O
Properties
C17H25NO3
Molar mass 291.3853
Appearance colorless oily substance
Solubility in water 0.181 mg/ml
Solubility in organic solvents high
Pharmacology
Drug class antifungal
D01AA04 (WHO)
topical (cream or solution)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pecilocin (brand name Variotin) is a pyrrolidine anti-fungal. It is produced by Paecilomyces varioti Bainer var. antibioticus and was first isolated by Setsuo Takeuchi in 1959. Later, it was established that other fungi also produce this compound, which include Aspergillus candidus and Aspergillus montenegroi.

Uses

Pecilocin is indicated for topical treatment of fungal infections of skin and its adnexa, 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). 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.

Biosynthesis

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

References

  1. ↑ "Pecilocin | C17H25NO3 | ChemSpider". www.chemspider.com. Retrieved 2020-04-08.
  2. ↑ Takeuchi S, Yonehara H, Umezawa H (September 1959). "Studies on variotin, a new antifungal antibiotic. I. Preparations and properties of variotin". The Journal of Antibiotics. 12: 195–200. PMID 13855011.
  3. ↑ Ngo MT, Van Nguyen M, Han JW, Kim B, Kim YK, Park MS, et al. (2021-12-23). "Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites". Frontiers in Microbiology. 12 804333. doi:10.3389/fmicb.2021.804333. PMC 8733401. PMID 35003037.
  4. ↑ Piechal A, Iwańczyk A, Groszyk E, Kostrzewa-Itrych A, Rząca K, Itrych B, Celiński A, eds. (2019). Leki współczesnej terapii (Wydanie XXII ed.). Warszawa: Medical Tribune Polska. ISBN 978-83-951310-6-6.
  5. 1 2 Gottlieb D, Shaw PD, eds. (1967). Biosynthesis. Berlin, Heidelberg: Springer Berlin Heidelberg. doi:10.1007/978-3-662-38441-1. ISBN 978-3-662-37650-8.
  6. ↑ Aronson JK, ed. (2016). "Antifungal azoles and other antifungal drugs for topical use". Meyler's Side Effects of Drugs. Elsevier. pp. 602–605. doi:10.1016/b978-0-444-53717-1.00312-7. ISBN 978-0-444-53716-4. Retrieved 2025-02-08.