Structure via PubChem · Public domain (PubChem)
pecilocin
Sign in to saveAlso known as 1-[(2E,4E,6E,8R)-8-hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one
Pecilocin (brand name Variotin) is a pyrrolidine anti-fungal. It is produced by Paecilomyces varioti Bainer var. antibioticus and was first isolated by Setsuo Takeuchi in 1959. Later, it was established that other fungi also produce this compound, which include Aspergillus candidus and Aspergillus montenegroi.
Chemical data
- Formula
- C17H25NO3
- Molecular weight
- 291.4 g/mol
- IUPAC name
- 1-[(2E,4E,6E,8R)-8-hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one
- SMILES
- CCCC[C@H](/C=C(\C)/C=C/C=C/C(=O)N1CCCC1=O)O
- InChIKey
- ZYPGADGCNXOUJP-CXVPHVKISA-N
- XLogP
- 2.9
- Polar surface area
- 57.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 291.183444
Show 4 more facts
- chemical formula
- C₁₇H₂₅NO₃
- canonical SMILES
- CCCCC(C=C(C)C=CC=CC(=O)N1CCCC1=O)O
- isomeric SMILES
- CCCC[C@H](/C=C(\C)/C=C/C=C/C(=O)N1CCCC1=O)O
- medical condition treated
- dermatomycosis
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
5 sectionsContents
- Uses
- Antifungal spectrum
- Adverse effects
- Biosynthesis
- References
Pecilocin (brand name Variotin) is a pyrrolidine anti-fungal. It is produced by Paecilomyces varioti Bainer var. antibioticus and was first isolated by Setsuo Takeuchi in 1959. Later, it was established that other fungi also produce this compound, which include Aspergillus candidus and Aspergillus montenegroi.
== Uses == Pecilocin is indicated for topical treatment of fungal infections of skin and its adnexa, i.e.: skin mycoses (including tinea versicolor) onchomycosis scalp infections (e.g. tinea capitis)
Excerpted from Wikipedia’s “pecilocin” article, available under the CC BY-SA 4.0 licence.