Benzylamine and thiocarbamate derivatives
The benzylamine group includes butenafine (Mentax), which is similar in spectrum and mechanism of action to allylamines. This cream is applied once daily. It demonstrates high efficacy against dermatophytes and the causative agent of pityriasis versicolor, although it is somewhat inferior to azole compounds in the treatment of cutaneous candidiasis.
Tolnaftate is a thiocarbamate derivative. Available as a cream, gel, solution, and powder, it is used twice a day for the treatment and prevention of mycoses. An important feature of tolnaftate is its complete ineffectiveness against fungi of the genus Candida.
Morpholine derivatives and halogenated compounds
Drugs based on amorolfine are morpholine derivatives. Their mechanism of action is associated with the inhibition of ergosterol synthesis enzymes (delta-14-reductase and delta-7-8-isomerase), which leads to the accumulation of defective sterols and the destruction of fungal cell membranes. The type of action can be either fungistatic or fungicidal depending on the concentration. The main indication for amorolfine is fungal nail infections (onychomycosis).
Haloprogin is a halogenated phenol ether available in cream and solution forms. It is poorly absorbed through the epidermis and broken down in the body into trichlorophenol. It is prescribed in 2–4 week courses with twice-daily application for dermatophytosis and pityriasis versicolor.
Ciclopirox and other topical antimycotics
Ciclopirox (Batrafen) has a pronounced fungicidal effect. The variety of its dosage forms is striking:
- Cream, gel, suspension, lotion: prescribed for pityriasis versicolor, cutaneous mycoses, and vaginal candidiasis.
- Nail lacquer: used for onychomycosis.
- Shampoo (1%): effective for scalp seborrheic dermatitis.
Among other agents, undecylenic acid preparations stand out (included in zinc undecan, undecin, mycoseptin ointments), as well as the topical antiseptic potassium iodide. Special mention should be made of dequalinium chloride, a bis-quaternary ammonium compound with dual action (antibacterial and fungicidal). It is used in ointment form for skin infections and as lozenges for throat inflammation and oral candidiasis.
Briefly: answers to topical questions
What side effects does haloprogin cause when applied topically?
When applied topically, haloprogin can cause irritation, itching, burning, and increased maceration at the application site.
Amorolfine works on nails (morpholine — "sea of nails" / "mor-of-nails"), while ciclopirox is versatile: ranging from scalp shampoo to nail lacquer and skin cream.
Class and exam questions
Is butenafine effective in cutaneous candidiasis?
No, despite high activity against dermatophytosis and pityriasis versicolor, butenafine is inferior to azole drugs in the treatment of cutaneous candidiasis.
What are the main indications for prescribing amorolfine?
Amorolfine is used primarily for the treatment of onychomycosis due to its ability to disrupt ergosterol synthesis in fungal membranes.
In what forms is ciclopirox available?
Ciclopirox is available as a cream, gel, suspension, lotion, special nail lacquer, and 1% scalp shampoo.
What else to study on this topic
- Biochemical mechanism of ergosterol synthesis and targets of amorolfine action
- Comparison of the efficacy of butenafine and azoles in various dermatophytoses
- Pharmacokinetic profile of haloprogin and its metabolism to trichlorophenol
- The role of combination ointments with undecylenic acid in dermatology
- Pharmacological properties of dequalinium chloride in oral cavity infections
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