Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H15Cl3N2S.HNO3 |
Molecular Weight | 460.762 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.ClC1=CC=C(CSC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1
InChI
InChIKey=CRKGMGQUHDNAPB-UHFFFAOYSA-N
InChI=1S/C18H15Cl3N2S.HNO3/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21;2-1(3)4/h1-9,12,18H,10-11H2;(H,2,3,4)
DescriptionSources: https://www.drugs.com/cdi/sulconazole-cream.html
Sources: https://www.drugs.com/cdi/sulconazole-cream.html
Sulconazole (trade name Exelderm) is an antifungal medication of the imidazole class. Sulconazole has a broad spectrum of antifungal activity in vitro and has been shown to be an effective topical antifungal agent for the management of superficial fungal infections of the skin, particularly dermatophytosis and tinea versicolor. Sulconazole inhibits the cytochrome P-450 isoenzyme, C-14-alpha-demethylase by binding to the heme iron of the enzyme. This results in a largely fungistatic effect. The selectivity of azole antifungal agents for pathogenic organisms compared with mammalian cells appears to depend on a preferred affinity of these drugs for fungal versus mammalian cytochrome P-450 sterol demethylases. Enzyme inhibition by sulconazole prevents the synthesis of ergosterol, a sterol found in fungal cell membranes but, in general, not in mammalian cell membranes. Additionally, lanosterol accumulates, which changes membrane permeability, cell volume, secondary metabolic effects, and causes defective cell division and growth inhibition. As sulconazole is primarily fungistatic, an intact immune system may be needed for infection resolution.In selected situations, sulconazole may have growth phase-dependent fungicidal activity against very susceptible organisms. The 1% concentration of sulconazole may greatly exceed the minimum inhibitory concentration and exert a direct physiochemical effect on the fungal cell membrane. The fungicidal effect may be due to hydrophobic interactions between sulconazole and unsaturated fatty acids in the membrane. Mammalian cells generally have little or no unsaturated fatty acids. Sulconazole may also prevent DNA and RNA synthesis and increase their degradation.Sulconazole has activity against many dermatophytes and yeast. One measure of the drug's antifungal activity is the relative inhibition factor (RIF). The RIF approaches 0% for a drug to which a fungus is highly sensitive and 100% for a drug that is non-inhibitory. The RIF values of sulconazole for Candida species, Aspergillus species, and dermatophytes are broadly similar to those of clotrimazole, econazole, ketoconazole, miconazole, and tioconazole. The mean RIF values were 69% (30—98%) for Candida species, 71% (61—82%) for Aspergillus species, and 12% (5—18%) for dermatophytes. Sulconazole is available as a cream or solution to treat skin infections such as athlete's foot, ringworm, jock itch, and sun fungus.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3390824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12611652 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | EXELDERM Approved UseEXELDERM (sulconazole nitrate, USP) CREAM, 1.0% is an antifungal agent indicated for the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, and Microsporum canis,* and for the treatment of tinea versicolor. Launch Date1989 |
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Curative | EXELDERM Approved UseEXELDERM (sulconazole nitrate, USP) CREAM, 1.0% is an antifungal agent indicated for the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, and Microsporum canis,* and for the treatment of tinea versicolor. Launch Date1989 |
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Curative | EXELDERM Approved UseEXELDERM (sulconazole nitrate, USP) CREAM, 1.0% is an antifungal agent indicated for the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, and Microsporum canis,* and for the treatment of tinea versicolor. Launch Date1989 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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4.81 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7320848 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULCONAZOLE plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7320848 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULCONAZOLE plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Doses
Dose | Population | Adverse events |
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1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: RS 44872 |
unhealthy, adult n = 286 Health Status: unhealthy Condition: Tinea pedis | Tinea cruris | Tinea corporis | Cutaneous candidiasis | Tinea versicolor Age Group: adult Sex: M+F Population Size: 286 Sources: Page: RS 44872 |
Disc. AE: Contact dermatitis, Pruritus... AEs leading to discontinuation/dose reduction: Contact dermatitis Sources: Page: RS 44872Pruritus |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Contact dermatitis | Disc. AE | 1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: RS 44872 |
unhealthy, adult n = 286 Health Status: unhealthy Condition: Tinea pedis | Tinea cruris | Tinea corporis | Cutaneous candidiasis | Tinea versicolor Age Group: adult Sex: M+F Population Size: 286 Sources: Page: RS 44872 |
Pruritus | Disc. AE | 1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: RS 44872 |
unhealthy, adult n = 286 Health Status: unhealthy Condition: Tinea pedis | Tinea cruris | Tinea corporis | Cutaneous candidiasis | Tinea versicolor Age Group: adult Sex: M+F Population Size: 286 Sources: Page: RS 44872 |
PubMed
Title | Date | PubMed |
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Percutaneous absorption of sulconazole nitrate in humans. | 1988 Jun |
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In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp. | 1992 Apr |
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Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs. | 2001 Aug |
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Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay. | 2002 Aug |
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Comparative study of the enantiomeric resolution of chiral antifungal drugs econazole, miconazole and sulconazole by HPLC on various cellulose chiral columns in normal phase mode. | 2002 Jan 15 |
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Inhibition of cytochromes P450 by antifungal imidazole derivatives. | 2002 Mar |
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Topical antifungal treatment cures exit-site fungal infection. | 2002 Oct |
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Rapid method development for chiral separation in drug discovery using multi-column parallel screening and circular dichroism signal pooling. | 2004 Sep 17 |
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Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column. | 2005 Aug 12 |
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Athlete's foot. | 2005 Dec |
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Aurintricarboxylic acid inhibits influenza virus neuraminidase. | 2009 Feb |
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Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay. | 2009 Sep 14 |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/sulconazole.html
Tinea corporis/tinea cruris/tinea versicolor: Topical: Apply a small amount to the affected and surrounding skin areas once or twice daily for 3 weeks
Tinea pedis: Topical: Cream: Apply a small amount to the affected area twice daily for 4 weeks
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23122865
HEK 293T cells were transfected with mouse Ido1, Ido2 or Tdo2 expression constructs for the enzymatic activity assay. One day after transfection the medium was replaced with phenol red-free medium supplemented with LTrp (1 mM for library screening or 400 lM for all other experiments). All compounds tested for effects on enzymatic activity were dissolved in dimethyl sulfoxide (DMSO) and added to the transfected cells, along with a DMSO control. On the following day, the protein in the medium was precipitated with the addition of trichloroacetic acid (final concentration 4%) and centrifugation at 1500 rcf, 10_ C for 45 min. Supernates were carefully removed and added to an equal volume of 2% (w/v) Ehrlich’s reagent, 4-(Dimethylamino) benzaldehyde in glacial acetic acid. Absorbances were measured at 485 nm using the SPECTRA MAX 190 microplate spectrophotometer (Molecular Devices, USA).
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ACTIVE MOIETY
SUBSTANCE RECORD