Sertaconazole: Difference between revisions

Sertaconazole
Clinical data
License data	US FDA: Sertaconazole;
Routes of; administration	Topical
ATC code	D01AC14 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	>99% to plasma
Identifiers
	IUPAC name 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole;
CAS Number	99592-32-2;
PubChem CID	65863;
DrugBank	APRD00305;
ChemSpider	59273;
UNII	72W71I16EG;
CompTox Dashboard (EPA)	DTXSID0048551 ;
Chemical and physical data
Formula	C20H15Cl3N2OS
Molar mass	437.77 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(c(Cl)c1)C(OCc2c3cccc(Cl)c3sc2)Cn4ccnc4;
	(verify)

Browse history interactively

← Previous edit Next edit →

Content deleted Content added

VisualWikitext

Inline

Revision as of 04:19, 19 November 2010

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 several known mechanisms of action. It considered fungistatic, fungicidal, antibacterial, antiinflammatory, antitrichomonal, andantipruritic.

Likee other imidazole antifungals, sertaconazole 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 is 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

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.[1].Drugs 2009; 69(3):339-359.doi: 10.2165/00003495-200969030-00009.

External links

Ertaczo prescribing information

[serta-1] Croxtall JD, Plosker GL.[1].Drugs 2009; 69(3):339-359.doi: 10.2165/00003495-200969030-00009.

[1]

@@ Line 32: / Line 32: @@
 ==Mechanism of action==
-Sertaconazole has different mechanisms of action: '''Fungistatic''', '''fungicidal''', '''antibacterial''', '''antiinflammatory''', '''antitrichomonal''', '''antipruritic''' actions.
+Sertaconazole has several known mechanisms of action. It considered '''fungistatic''', '''fungicidal''', '''antibacterial''', '''antiinflammatory''', '''antitrichomonal''', and'''antipruritic'''.
-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.
+Likee other imidazole antifungals, sertaconazole 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.
-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.
+Chemically, sertaconazole contains a benzothiophene ring which makes is 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 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 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 has antibacterial action. It is hypothysed that it happens like its fungicidal mechanism of action: By means of benzothiophene ring's similarity to tryptophan.
+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 is shown that sertaconazole can kill Trichomonas vaginalis on in vitro experiments. This mechanism of action is unknown.
+It has also been shown that sertaconazole can kill Trichomonas vaginalis in vitro. The exact mechanism of action is as yet unknown.
-Sertaconazole also inhibits the dimorfic transformation of Candida albicans into pathogenic fungi.
+Sertaconazole also appears to inhibit the dimorphic transformation of Candida albicans into pathogenic fungi.
 ==Microbiology==