Pecilocin

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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 ☒N
    Key: ZYPGADGCNXOUJP-CXVPHVKISA-N ☒N
  • 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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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

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