Product Name

Ciclopirox

CAS Number

29342-05-0

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Product Name:
Ciclopirox
CAS Number:
29342-05-0
Indication:
Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.
Mode of Action:

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.

Pharmacodynamics:

Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.

Metabolism:

Glucuronidation is the main metabolic pathway of ciclopirox.

Toxicity:

Oral LD50 in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.

IUPAC:
6-cyclohexyl-1-hydroxy-4-methyl-1, 2-dihydropyridin-2-one
ATC:
D01AE14 G01AX12
PubChem:
2749
DrugBank:
DB01188 (APRD00871)
Formula:
C12H18Cl2N2O
Molecular Mass:
207.2689
Synonyms:
Ciclopirox Olamin Ciclopirox-Olamin ciclopiroxolamine Ciclopiroxum [INN-Latin] HOE 296b HOE-296b
SMILES:
CC1=CC(=O)N(O)C(=C1)C1CCCCC1
AHFS Code:
84:04.08.20
InChi:
SCKYRAXSEDYPSA-UHFFFAOYSA-N
General Reference:
General Reference:

 

  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. Pubmed
  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. Pubmed

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