Sertaconazole

Last updated
Sertaconazole
Sertaconazole.svg
Sertaconazole ball-and-stick.png
Clinical data
Trade names Ertaczo, Dermofix, Zalain
AHFS/Drugs.com Monograph
MedlinePlus a608047
License data
Routes of
administration
Topical
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability Negligible
Protein binding >99% to plasma
Identifiers
  • (RS)-1-{2-[(7-Chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-Benzothiophenes
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H15Cl3N2OS
Molar mass 437.76 g·mol−1
3D model (JSmol)
  • Clc1ccc(c(Cl)c1)C(OCc2c3cccc(Cl)c3sc2)Cn4ccnc4
  • 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 Yes check.svgY
  • Key:JLGKQTAYUIMGRK-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Sertaconazole, sold under the brand name Ertaczo among others, is an antifungal medication of the Benzothiophene class. It is available as a cream to treat skin infections such as athlete's foot.

Contents

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

Medical uses

In randomized, double-blind, multicentre trials of 3 to 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 compared 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.[ citation needed ]

Pharmacology

Pharmacodynamics

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 benzothiophene 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 activates 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.

The following fungal organisms, among others, are known to be susceptible to sertaconazole:

Chemistry

Sertaconazole contains a stereocenter and consists of two enantiomers. The pharmaceutical drug is a racemate, an equal mixture of the (R)- and (S)-forms. [2]

Enantiomers of sertaconazole
(R)-Sertaconazol Structural Formula V1.svg
(R)-Sertaconazole
CAS number: 583057-48-1
(S)-Sertaconazol Structural Formula V1.svg
(S)-Sertaconazole
CAS number: 583057-51-6

Related Research Articles

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.

<span class="mw-page-title-main">Nystatin</span> Antifungal medication

Nystatin, sold under the brand name Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

<span class="mw-page-title-main">Fluconazole</span> Antifungal medication

Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.

<span class="mw-page-title-main">Ergosterol</span> Chemical compound

Ergosterol (ergosta-5,7,22-trien-3β-ol) is a mycosterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. In human nutrition, ergosterol is a provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.

<span class="mw-page-title-main">Tolnaftate</span> Chemical compound

Tolnaftate (INN) is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.

<span class="mw-page-title-main">Terbinafine</span> Antifungal medication

Terbinafine is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either taken by mouth or applied to the skin as a cream or ointment. The cream and ointment should not be used for fungal nail infections.

<span class="mw-page-title-main">Ciclopirox</span> Antifungal medication

Ciclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against tinea versicolor. It is often used clinically as ciclopirox olamine, the olamine salt of ciclopirox.

<span class="mw-page-title-main">Terconazole</span> Chemical compound

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.

<span class="mw-page-title-main">Butenafine</span> Chemical compound

Butenafine, sold under the brand names Lotrimin Ultra, Mentax, and Butop, is a synthetic benzylamine derived antifungal drug.

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

<span class="mw-page-title-main">Naftifine</span> Chemical compound

Naftifine hydrochloride is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis.

<span class="mw-page-title-main">Fenticonazole</span> Chemical compound

Fenticonazole is an imidazole antifungal drug, used locally as the nitrate in the treatment of vulvovaginal candidiasis. It is active against a range of organisms including dermatophyte pathogens, Malassezia furfur, and Candida albicans. Fenticonazole has also been shown to exhibit antibacterial action, with a spectrum of activity that includes bacteria commonly associated with superinfected fungal skin and vaginal infections, and antiparasitic action against the protozoan Trichomonas vaginalis.

<span class="mw-page-title-main">Clotrimazole</span> Chemical compound

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.

<span class="mw-page-title-main">Abafungin</span> Chemical compound

Abafungin (INN) is a broad-spectrum antifungal agent with a novel mechanism of action for the treatment of dermatomycoses.

<i>Microsporum audouinii</i> Species of fungus

Microsporum audouinii is an anthropophilic fungus in the genus Microsporum. It is a type of dermatophyte that colonizes keratinized tissues causing infection. The fungus is characterized by its spindle-shaped macroconidia, clavate microconidia as well as its pitted or spiny external walls.

Econazole/triamcinolone is a combination drug, consisting of econazole and triamcinolone.

<span class="mw-page-title-main">Luliconazole</span> Chemical compound

Luliconazole, trade names Luzu among others, is an imidazole antifungal medication. As a 1% topical cream, It is indicated for the treatment of athlete's foot, jock itch, and ringworm caused by dermatophytes such as Trichophyton rubrum, Microsporum gypseum, and Epidermophyton floccosum.

Liranaftate is a topical antifungal drug. It is used as a 2% cream used to treat tinea pedis, tinea corporis (ringworm), and tinea cruris. It was approved for use in Japan in August 2000.

Topical antifungaldrugs are used to treat fungal infections on the skin, scalp, nails, vagina or inside the mouth. These medications come as creams, gels, lotions, ointments, powders, shampoos, tinctures and sprays. Most antifungal drugs induce fungal cell death by destroying the cell wall of the fungus. These drugs inhibit the production of ergosterol, which is a fundamental component of the fungal cell membrane and wall.

References

  1. Croxtall JD, Plosker GL (2009). "Sertaconazole: a review of its use in the management of superficial mycoses in dermatology and gynaecology". Drugs. 69 (3): 339–59. doi:10.2165/00003495-200969030-00009. PMID   19275277. S2CID   195684055.
  2. Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Vol. 57. Frankfurt/Main: Rote Liste Service GmbH (Hrsg.). 2017. p. 217. ISBN   978-3-946057-10-9.