Sertaconazole

Sertaconazole

File:Sertaconazole.svg
Systematic (IUPAC) name
1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
Clinical data
[[Regulation of therapeutic goods |Template:Engvar data]]	US FDA: Sertaconazole
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	>99% to plasma
Identifiers
CAS Number	99592-32-2
ATC code	D01AC14 (WHO)
PubChem	CID 65863
DrugBank	APRD00305
Chemical data
Formula	C20H15Cl3N2OS
Molar mass	437.77 g/mol[[]]
(verify)

Sertaconazole nitrate (Ertaczo, Dermofix) is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot.

It is also available in a vaginal tablet form. The most popular of these is Gyno-Dermofix

Mechanism of action

Sertaconazole has different mechanisms of action: Fungistatic, fungicidal, antibacterial, antiinflammatory, antitrichomonal, antipruritic actions.

It inhibits, like other imidazole antifungals, the synthesis of ergosterol by inhibiting the 14α-demethylase enzyme. Ergosterol is a component of the fungal cell membrane. By this way, the fungal cell can not grow larger and multiply. The hyphae formation of the Candida will be impeded. This is the fungistatic action of sertaconazole.

Uniquely, sertaconazole owns a benzothiophene ring in its structure. It resembles an amino acid, tryptophan, which can be found on the fungal membrane. The benzothiophene ring takes the place of tryptophan, that is it mimics tryptophan. So pores, holes and craters are formed on the fungal cell membrane. These pores open at the 10th minute after application. When the pore forms the fungal cell loses its intracellular content. Mainly, ATP is lost. The fungus lacks energy and dies. After 1 hour of application, 90% of the fungi die. This is the fungicidal action of sertaconazole. Sertaconazole is the sole antifungal, which owns this mechanism of action.

Sertaconazole has also antiinflammatory and antipruritic action. It reduces the release of cytokines from activated lymphocytes. It is shown that sertaconazole activatates of the p38-COX-2-PGE2 pathway which is related to sertaconazole's fungicidal action.

Sertaconazole has antibacterial action. It is hypothysed that it happens like its fungicidal mechanism of action: By means of benzothiophene ring's similarity to tryptophan.

It is shown that sertaconazole can kill Trichomonas vaginalis on in vitro experiments. This mechanism of action is unknown.

Sertaconazole also inhibits the dimorfic transformation of Candida albicans into pathogenic fungi.

Microbiology

Susceptible organisms

• Candida albicans
• Epidermophyton floccosum
• Trichophyton rubrum
• Trichophyton mentagrophytes

Therapeutic efficacy

In randomized, double-blind, multicentre trials of 3–6 weeks' duration (n=127-383), a significantly greater number of patients with tinea of the glabrous skin and tinea pedis receiving a topical 2% sertaconazole cream once or twice daily achieved a successful mycological cure copmared with recipients of a placebo cream.

Side effects

Side effects were rarely reported with sertaconazole therapy, but may include contact dermatitis, burning on application site and skin dryness.

External links

• Ertaczo prescribing information

fr:Sertaconazole