Ciclopirox

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Structural formula
Structure of Cicloprix
General
Non-proprietary name Ciclopirox
other names
  • 6-Cyclohexyl-1-hydroxy-4-methyl-2 (1 H ) -pyridinone
  • Loprox
Molecular formula C 12 H 17 NO 2
Brief description

white to yellowish white, crystalline powder

External identifiers / databases
CAS number
  • 29342-05-0
  • 41621-49-2 (olamine)
PubChem 2749
DrugBank DB01188
Wikidata Q419468
Drug information
ATC code
properties
Molar mass 207.27 g · mol -1
Physical state

firmly

Melting point

144 ° C

solubility

Slightly soluble in water, easily soluble in dichloromethane and ethanol

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
Toxicological data

2100–3600 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ciclopirox is a drug that is used as a local antifungal agent . It was patented by Hoechst in 1970 and 1975 . Ciclopirox is a pyridone - descendant . Except ciclopirox itself will be ethanolamine - salt Ciclopiroxolamine pharmaceutically also used as an antifungal drug.

application areas

Ciclopirox is a broad-spectrum antifungal drug that works against candida and dermatophytes . It is used to treat dermatomycosis and onychomycosis, and vaginal yeast infections . It also has antibacterial and anti-inflammatory effects. A contraindication is pregnancy.

effect

Ciclopirox disrupts the function of the fungal cell membrane . It penetrates deeply into the skin and nails and is well tolerated. Ciclopirox has a fungicidal and sporocidal effect , it inhibits metabolic processes that are involved in important enzymatic reactions, so it induces the outflow of vital cell components.

Trade names

Monopreparations

Batrafen (D, A), Ciclocutan (D, A), Ciclopoli (D), Dafnegil (CH), Inimur myko (D), Kitonail (A), Nagel Batrafen (D), Sebiprox (D, CH), Stieprox ( A), Nibulen ( TR ), various generics (D, CH).

literature

  • C.-J. Estler (founder) u. H. Schmidt (Ed.): Pharmacology and Toxicology . 6th edition, Schattauer, 2007, p. 843.
  • J. Falbe et al. M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition, Thieme, 1996, p. 750.
  • HJ Roth u. H. Fenner: Drugs . Thieme, 1988, p. 121.
  • Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , pp. 254-258 ( antimycotics for local therapy ).

Individual evidence

  1. ↑ a b c data sheet CICLOPIROX CRS (PDF) at EDQM , accessed on August 21, 2008.
  2. ↑ J. Falbe et al. M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition, Thieme, 1996, p. 750.
  3. ↑ a b Data sheet Ciclopirox olamine from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
  4. ↑ Kimberly M. Carlson-Banning, Andrew Chou, Zhen Liu, Richard J. Hamill, Yongcheng Song, Lynn Zechiedrich: Toward Repurposing Ciclopirox as an Antibiotic against Drug-Resistant Acinetobacter baumannii, Escherichia coli, and Klebsiella pneumoniae. In: PLOS ONE . Volume 8, Number 7, 2013, e69646, doi : 10.1371 / journal.pone.0069646 . PMID 23936064 .
  5. ↑ Red List online, as of September 2009.
  6. ↑ AM comp. d. Switzerland, as of September 2009.
  7. ↑ AGES-PharmMed, as of September 2009.