2266. Ciclopirox

Nomenclature

CAS number: 29342-05-0
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone.
C12H17NO2; mol wt 207.27.
C 69.54%, H 8.27%, N 6.76%, O 15.44%.

Description and 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).

Chemical structure

Properties

Solid, mp 144°.

Derivative

Ethanolamine salt (1:1).

Nomenclature

CAS number: 41621-49-2
Ciclopirox olamine; HOE-296; Batrafen (HMR); Brumixol (Bruschettini); Ciclochem (Novag); Dafnegin (Poli); Loprox (HMR); Micoxolamina (Dompé); Mycoster (Fabre).
C14H24N2O3; mol wt 268.35.
C 62.66%, H 9.01%, N 10.44%, O 17.89%.

Properties

LD50 in mice, rats (mg/kg): 2898, 3290 orally (Alpermann, Schutz).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic)