Sertaconazole

drugbox
IUPAC_name = 1- [2- [(7-chlorobenzothiophen-3-yl) methoxy] - 2-(2,4-dichlorophenyl)- ethyl] imidazole

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CAS_number = 99592-32-2
ATC_prefix = D01
ATC_suffix = AC14
ATC_supplemental =
PubChem = 65863
DrugBank = APRD00305
C = 20 | H = 15 | Cl = 3 | N = 2 | O = 1 | S = 1
molecular_weight = 437.77 g/mol
bioavailability = Negligible
protein_bound = >99% to plasma
metabolism =
elimination_half-life =
pregnancy_US = C
licence_US = Sertaconazole
legal_status = Rx-only
routes_of_administration = Topical

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

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 aciton 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

usceptible organisms

*"Candida albicans"
*"Epidermophyton floccosum"
*"Trichophyton rubrum"
*"Trichophyton mentagrophytes"

ide effects

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

External links

* [http://www.biafine.orthoneutrogena.com/Ertaczo_PI_FINAL_0324.pdf Ertaczo prescribing information]