6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolammonium salt
IDENTITY
CAS Number:
41621-49-2
MDL Number:
MFCD00078997
MF:
C14H24N2O3
MW:
268.35
EINECS:
255-464-9
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:
>98% (HPLC), powder
Physical Form (at 20°C):
Solid
Melting Point:
152-156°C
Long-Term Storage:
Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
Not hazardous material
BIOLOGICAL INFO
Solubility:
MeOH: 50mg/mL
Application(s):
Antifungal agent working as an iron chelator
REVIEW Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
REFERENCES
[1]
Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17.
[2]
Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24.
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