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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
Structure of SULCONAZOLE NITRATE

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)

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
EXELDERM
Curative
EXELDERM
Curative
EXELDERM

Cmax

ValueDoseCo-administeredAnalytePopulation
4.81 μg/mL
1000 mg single, oral
SULCONAZOLE plasma
Canis lupus

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
1000 mg single, oral
SULCONAZOLE plasma
Canis lupus

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
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
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).