Ciclopirox


Ciclopirox is a medication used for the treatment of moderate onychomycosis of fingernails and toenails, and for the treatment of seborrheic dermatitis.
In 2023, it was the 278th most commonly prescribed medication in the United States, with more than 700,000 prescriptions.

Medical uses

Ciclopirox is indicated as topical treatment in immunocompetent people with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum,; and for the treatment of seborrheic dermatitis.

Nail infections

In addition to other formulations, ciclopirox is used in lacquers for topical treatment of onychomycosis. A meta-analysis of the six trials of nail infections available in 2009 concluded that they provided evidence that topical ciclopirox had poor cure rates, and that amorolfine might be substantially more effective, but more research was required. "Combining data from 2 trials of ciclopiroxolamine versus placebo found treatments failure rates of 61% and 64% for ciclopiroxolamine. These outcomes followed long treatment times and this makes ciclopiroxolamine a poor choice for nail infections. Better results were observed with the use of amorolfine lacquer; 6% treatment failure rates were found after 1 month of treatment but these data were collected on a very small sample of people and these high rates of success might be unreliable."
Efinaconazole, an azole antifungal, led to cure rates two or three times better than the next-best topical treatment, ciclopirox.

Pharmacology

Pharmacodynamics

In contrast to the azoles and other antimycotic drugs, the mechanism of action of ciclopirox is poorly understood. However, loss of function of certain catalase and peroxidase enzymes has been implicated as the mechanism of action, as well as various other components of cellular metabolism. In a study conducted to further elucidate ciclopirox's mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures as well as some elements of intracellular transport.

Chemistry

Ciclopirox is a N-hydroxypyridone. Structurally, ciclopirox is the N-oxide of a 2-hydroxypyridine derivative and therefore can be termed a hydroxypyridine antifungal agent. Additionally, the structure as drawn above is the lactam tautomer and indicates the molecule being an N-hydroxy-2-pyridone. Hence the classification of ciclopirox as a 2-pyridone antifungal agent.

Society and culture

Brand names

It is sold under many brand names worldwide.

Research

In 2007 it was investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur. Initial results showed similar efficacy to ketoconazole with a relative increase in subjective symptom relief due to its inherent anti-inflammatory properties.