Ciclopirox

Title: Ciclopirox
CAS Registry Number: 29342-05-0
CAS Name: 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
Molecular Formula: C12H17NO2
Molecular Weight: 207.27
Percent Composition: C 69.54%, H 8.27%, N 6.76%, O 15.44%
Literature References: Broad spectrum antimycotic agent with some antibacterial activity. Prepn: G. Lohaus, W. Dittmar, ZA 6906039; eidem, US 3883545 (1970, 1975 both to Hoechst). In vitro study: eidem, Arzneim.-Forsch. 23, 670 (1973). Series of articles on pharmacokinetics, pharmacology, teratology, toxicity studies: Oyo Yakuri 9, 57-115 (1975), C.A. 83, 53159d, 53538b, 53539c, 71844c, 90833q (1975). Series of articles on chemistry, mechanism of action, toxicology, clinical trials: Arzneim.-Forsch. 31, 1309-1386 (1981). Toxicity data: H. G. Alpermann, E. Schutz, ibid. 1328. Review: S. G. Jue et al., Drugs 29, 330-341 (1985). Review of clinical experience in seborrheic dermatitis: A. Starova, R. Aly, Expert Opin. Drug Saf. 4, 235-239 (2005).
Properties: Solid, mp 144°.
Melting point: mp 144°
Derivative Type: Ethanolamine salt (1:1)
CAS Registry Number: 41621-49-2
Additional Names: Ciclopirox olamine
Manufacturers' Codes: HOE-296
Trademarks: Batrafen (HMR); Brumixol (Bruschettini); Ciclochem (Novag); Dafnegin (Poli); Loprox (HMR); Micoxolamina (Domp?; Mycoster (Fabre)
Molecular Formula: C14H24N2O3
Molecular Weight: 268.35
Percent Composition: C 62.66%, H 9.01%, N 10.44%, O 17.89%
Properties: LD50 in mice, rats (mg/kg): 2898, 3290 orally (Alpermann, Schutz).
Toxicity data: LD50 in mice, rats (mg/kg): 2898, 3290 orally (Alpermann, Schutz)
Therap-Cat: Antifungal.
Keywords: Antifungal (Synthetic).
Ciclosidomine Cicrotoic Acid Cicutoxin Cidofovir Cifenline

Ciclopirox
Ciclopirox.svg
Systematic (IUPAC) name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Clinical data
Trade names Loprox
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a604021
Pregnancy cat. B
Legal status -only (US) Rx-only (CA)
Routes Topical (applied as a nail lacquer or shampoo)
Pharmacokinetic data
Bioavailability <5% with prolonged use
Protein binding 94 to 97%
Half-life 1.7 hours
Identifiers
CAS number 29342-05-0 YesY
ATC code D01AE14 G01AX12
PubChem CID 2749
DrugBank DB01188
ChemSpider 2647 YesY
UNII 19W019ZDRJ YesY
KEGG D03488 YesY
ChEBI CHEBI:453011 YesY
ChEMBL CHEMBL1413 YesY
Chemical data
Formula C12H17NO2 
Mol. mass 207.269 g/mol
 YesY (what is this?)  (verify)

Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor.[1]