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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL486174 ;
ChemSpider	4445371 ;
ECHA InfoCard	100.039.182
EC Number	243-116-9;
KEGG	D01458 ;
PubChem CID	5282176;
UNII	TSA7W27MF8 ;
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 Key: ZYPGADGCNXOUJP-CXVPHVKISA-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). verify (what is ?) 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

^ "Pecilocin | C17H25NO3 | ChemSpider". www.chemspider.com. Retrieved 2020-04-08.
^ 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.
^ 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.
^ 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.
^ ^a ^b 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.
^ 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.

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

[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.

[Gottlieb_1967-5] 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.

[1]

[2]

[3]

[4]

[5]

[6]