Sertaconazole
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| Systematic (IUPAC) name |
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1-{2-[(7-Chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
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| Clinical data |
| AHFS/Drugs.com |
Consumer Drug Information |
| MedlinePlus |
a608047 |
| Licence data |
US FDA:link |
Pregnancy
category |
- US: C (Risk not ruled out)
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| Legal status |
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Routes of
administration |
Topical |
| Pharmacokinetic data |
| Bioavailability |
Negligible |
| Protein binding |
>99% to plasma |
| Identifiers |
| CAS Registry Number |
99592-32-2 Y |
| ATC code |
D01AC14 G01AF19 |
| PubChem |
CID: 65863 |
| DrugBank |
DB01153 Y |
| ChemSpider |
59273 Y |
| UNII |
72W71I16EG Y |
| KEGG |
D06883 Y |
| ChEBI |
CHEBI:82866 N |
| ChEMBL |
CHEMBL1201196 N |
| Chemical data |
| Formula |
C20H15Cl3N2OS |
| Molecular mass |
437.77 g/mol |
SMILES
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Clc1ccc(c(Cl)c1)C(OCc2c3cccc(Cl)c3sc2)Cn4ccnc4
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InChI
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InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2 Y
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Key:JLGKQTAYUIMGRK-UHFFFAOYSA-N Y
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| N (what is this?) (verify) |
Sertaconazole (Ertaczo, Dermofix, Konzert) 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.[citation needed]
Contents
- 1 Mechanism of action
- 2 Microbiology
- 2.1 Susceptible organisms
- 3 Therapeutic efficacy
- 4 Side effects
- 5 References
- 6 External links
Mechanism of action
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This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (April 2014) |
Sertaconazole has several known mechanisms of action. It is considered fungistatic, fungicidal, antibacterial, antiinflammatory, antitrichomonal, and antipruritic.[medical citation needed]
Like other imidazole antifungals, sertaconazole blocks the synthesis of ergosterol by inhibiting the 14α-demethylase enzyme. Ergosterol is a critical component of the fungal cell membrane. Inhibition of ergosterol synthesis prevents fungal cells from multiplying and impairs hyphae growth.
Chemically, sertaconazole contains a benzothiophene ring which makes it unique from other imidazole antifungals. A benzothiophene ring is a sulfur analogue of the indole ring found in the amino acid tryptophan. Tryptophan is found in the fungal membrane in addition to lipids such as ergosterol. The benzothiophene ring in sertaconazole mimics tryptophan and increases the drugs ability to form pores in the fungal cell membrane. If the cell membrane is made sufficiently leaky by these pores the fungal cell will die from loss of ATP and other effects which can include calcium disregulation. These pores are believed to open at about 10 minutes following topical application of sertaconazole. One hour following topical application, approximately 90% of fungal cells die from lack of energy (due to ATP loss) and general loss of homeostasis. Sertaconazole is thought to be the only imidazole antifungal with this mechanism of action.
Sertaconazole has also antiinflammatory and antipruritic action. It inhibits the release of proinflammatory cytokines from activated immune cells. It has been shown that sertaconazole activatates of the p38/COX2/PGE2 pathway. PGE2 can have a variety of important effects in the body including activation of the body's fever response.
Sertaconazole also has antibacterial action. It is hypothesized that the mechanism of action again involves sertaconazole's ability to form pores by mimicking tryptophan.
It has also been shown that sertaconazole can kill Trichomonas vaginalis in vitro. The exact mechanism of action is as yet unknown.
Sertaconazole also appears to inhibit the dimorphic transformation of Candida albicans into pathogenic fungi.
Microbiology
Susceptible organisms
- Candida albicans
- Epidermophyton floccosum
- Trichophyton mentagrophytes
- Trichophyton rubrum
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.[1]
Side effects
Side effects were rarely reported with sertaconazole therapy, but may include contact dermatitis, burning on application site and skin dryness.
References
- ^ Croxtall JD, Plosker GL. Adisonline.com, Drugs 2009; 69(3):339-359. doi:10.2165/00003495-200969030-00009.
External links
- Ertaczo prescribing information
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Antifungals (D01 and J02)
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Wall/
membrane |
Ergosterol
inhibitors |
Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
| Imidazoles |
- Topical: bifonazole
- butoconazole
- chlormidazole
- clotrimazole#
- croconazole
- econazole
- fenticonazole
- ketoconazole
- isoconazole
- miconazole#
- neticonazole
- omoconazole
- oxiconazole
- sertaconazole
- sulconazole
- tioconazole
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|
| Triazoles |
- Topical: (fluconazole#, fosfluconazole
- terconazole)
- Systemic: (fluconazole
- hexaconazole
- isavuconazole
- itraconazole
- posaconazole
- voriconazole)
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| Thiazoles |
|
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Polyene antimycotics
(ergosterol binding) |
- Topical: (hamycin
- natamycin
- nystatin#)
Systemic: (amphotericin B#, hamycin)
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Allylamines
(squalene monooxygenase
inhibitors) |
- Topical: (amorolfine
- butenafine
- naftifine
- terbinafine)
Systemic: terbinafine
|
|
|
β-glucan synthase
inhibitors |
- echinocandins (anidulafungin
- caspofungin
- micafungin)
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| Intracellular |
Pyrimidine analogues/
thymidylate synthase inhibitors |
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| Mitotic inhibitors |
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| Aminoacyl tRNA synthetase inhibitors |
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| Others |
- bromochlorosalicylanilide
- methylrosaniline
- tribromometacresol
- undecylenic acid
- polynoxylin
- chlorophetanol
- chlorphenesin
- ticlatone
- sulbentine
- ethylparaben
- haloprogin
- salicylic acid
- selenium disulfide#
- ciclopirox
- amorolfine
- dimazole
- tolnaftate
- tolciclate
- sodium thiosulfate#
- Whitfield's ointment#
- potassium iodide#
- taurolidine
- tea tree oil
- citronella oil
- lemon grass
- orange oil
- patchouli
- lemon myrtle
- PCP: pentamidine
- dapsone
- atovaquone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of fungal disease
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| Description |
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| Disease |
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| Treatment |
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