Ciclopirox ethanolamine

  • CAT Number: A000713
  • CAS Number: 41621-49-2
  • Molecular Formula: C12H17NO2.C2H7NO
  • Molecular Weight: 268.35
  • Purity: ≥95%
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Ciclopirox ethanolamine (Ciclopirox olamine, HOE 296) (CAS 41621-49-2)&nbsp;is a broad-spectrum antifungal agent working as an iron chelator.<br />
Ciclopirox significantly inhibits the growth of C. albicans strain SC5314 cells, with MIC<sub>80</sub>s of 1.0-2.0 &mu;g/mL, growth decreased dramatically at the concentrations of &gt;0.6 &mu;g/mL, and almost complete growth inhibition at concentration of 0.7 &mu;g/mL, unlike fluconazole which shows a much wider range of concentrations with intermediate inhibition. Like iron chelator bipyridine, Ciclopirox reduces cell growth by binding to iron ions, which can be reversed by addition of FeCl<sub>3</sub>. Moreover, Ciclopirox treatment at subinhibitory concentration (0.6 &mu;g/mL) only moderately reduces the virulence genes such as genes encoding secreted proteinases or lipases, but leads to a distinct up- or down-regulation of genes encoding iron permeases or transporters (FTR1, FTR2, and FTH1), a copper permease (CCC2), an iron reductase (CFL1), and a siderophore transporter (SIT1). Although the Candida drug resistance genes CDR1 and CDR2 are up-regulated after Ciclopirox treatment, no change in resistance or increased tolerance could be observed even after an incubation period of 6 months, in contrast to fluconazole in which the MICs for cells noticeably increase after 2 months.

Catalog Number A000713
CAS Number 41621-49-2
Synonyms

Ciclopirox ethanolamine; ciclopiroxolamine; Ciclobirox Olamine

Molecular Formula

C12H17NO2.C2H7NO

Purity 95%
Target ATPase
Solubility Soluble in DMSO > 10 mM
Storage 3 years -20C powder
IUPAC Name 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
InChI InChI=1S/C12H17NO2.C2H7NO/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;3-1-2-4/h7-8,10,15H,2-6H2,1H3;4H,1-3H2
InChIKey MBRHNTMUYWQHMR-UHFFFAOYSA-N
SMILES CC1=CC(=O)N(C(=C1)C2CCCCC2)O.C(CO)N
Reference

1.<span style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">Sigle, Hans-Christian, et al. &quot;Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans.&quot;&nbsp;</span><i style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">Journal of Antimicrobial Chemotherapy</i><span style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">&nbsp;55.5 (2005): 663-673.</span>

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