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
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

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 inclue Aspergillus candidus and Aspergillus montenegroi . ^[3]

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]

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. 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.