Pecilocin

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]

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
CAS Number	19504-77-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL486174 N
ChemSpider	4445371 N
ECHA InfoCard	100.039.182
EC Number	243-116-9
KEGG	D01458 Y
PubChem CID	5282176
UNII	TSA7W27MF8 N
CompTox Dashboard (EPA)	DTXSID5057676
InChI 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
SMILES CCCC[C@H](/C=C(\C)/C=C/C=C/C(=O)N1CCCC1=O)O
Properties
Chemical formula	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
ATC code	D01AA04 (WHO)
Routes of administration	topical (cream or solution)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Uses

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

• skin mycoses (including tinea versicolor)
• onchomycosis
• scalp infections (e.g. tinea capitis)

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]