:Pecilocin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408517523

| ImageFile = Pecilocin.svg

| PIN = 1-[(2E,4E,6E,8R)-8-Hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one

| OtherNames = {{langx|la|pecilocinum}}

| Section1 = {{Chembox Identifiers

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = TSA7W27MF8

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=19504-77-9

| PubChem=5282176

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01458

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 486174

| EINECS = 243-116-9

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4445371

| SMILES = CCCC[C@H](/C=C(\C)/C=C/C=C/C(=O)N1CCCC1=O)O

| 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

| InChIKey = ZYPGADGCNXOUJP-CXVPHVKIBE

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZYPGADGCNXOUJP-CXVPHVKISA-N

}}

| Section2 = {{Chembox Properties

| Formula=C₁₇H₂₅NO₃

| MolarMass=291.3853

| Appearance=colorless oily substance

| Density=

| MeltingPt=

| BoilingPt=

| Solvent1 = water

| Solubility1 = 0.181 mg/ml

| Solvent2 = organic solvents

| Solubility2 = high

}}

| Section6 = {{Chembox Pharmacology

| ATCCode_prefix = D01

| ATCCode_suffix = AA04

| Drug_class = antifungal

| AdminRoutes = topical (cream or solution)

}}

| Section7 = {{Chembox Hazards

| MainHazards=

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Pecilocin (brand name Variotin) is a pyrrolidine anti-fungal.{{Cite web|url=http://www.chemspider.com/Chemical-Structure.4445371.html|title=Pecilocin {{!}} C17H25NO3 {{!}} ChemSpider|website=www.chemspider.com|access-date=2020-04-08}} It is produced by Paecilomyces varioti Bainer var. antibioticus and was first isolated by Setsuo Takeuchi in 1959.{{cite journal | vauthors = Takeuchi S, Yonehara H, Umezawa H | title = Studies on variotin, a new antifungal antibiotic. I. Preparations and properties of variotin | journal = The Journal of Antibiotics | volume = 12 | pages = 195–200 | date = September 1959 | pmid = 13855011 | url = https://pubmed.ncbi.nlm.nih.gov/13855011/ }} Later, it was established that other fungi also produce this compound, which inclue Aspergillus candidus and Aspergillus montenegroi.{{cite journal | vauthors = Ngo MT, Van Nguyen M, Han JW, Kim B, Kim YK, Park MS, Kim H, Choi GJ | title = Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites | journal = Frontiers in Microbiology | volume = 12 | pages = 804333 | date = 2021-12-23 | pmid = 35003037 | pmc = 8733401 | doi = 10.3389/fmicb.2021.804333 | doi-access = free }}

Uses

Pecilocin is indicated for topical treatment of fungal infections of skin and its adnexa,{{Cite book |title=Leki współczesnej terapii |date=2019 |publisher=Medical Tribune Polska |isbn=978-83-951310-6-6 | veditors = Piechal A, Iwańczyk A, Groszyk E, Kostrzewa-Itrych A, Rząca K, Itrych B, Celiński A |edition=Wydanie XXII |location=Warszawa }} 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).{{Cite book |url=https://link.springer.com/10.1007/978-3-662-38441-1 |title=Biosynthesis |date=1967 |publisher=Springer Berlin Heidelberg |isbn=978-3-662-37650-8 | veditors = Gottlieb D, Shaw PD |location=Berlin, Heidelberg |language=en |doi=10.1007/978-3-662-38441-1 }} 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.{{cite book | veditors = Aronson JK | chapter = Antifungal azoles and other antifungal drugs for topical use |date=2016 |title = Meyler's Side Effects of Drugs |pages=602–605 | chapter-url=https://linkinghub.elsevier.com/retrieve/pii/B9780444537171003127 |access-date=2025-02-08 |publisher=Elsevier |language=en |doi=10.1016/b978-0-444-53717-1.00312-7 |isbn=978-0-444-53716-4}}

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

Category:Antifungals