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Details

Stereochemistry RACEMIC
Molecular Formula C18H15Cl3N2S
Molecular Weight 397.749
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULCONAZOLE

SMILES

ClC1=CC=C(CSC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

InChI

InChIKey=AFNXATANNDIXLG-UHFFFAOYSA-N
InChI=1S/C18H15Cl3N2S/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/h1-9,12,18H,10-11H2

HIDE SMILES / InChI

Molecular Formula C18H15Cl3N2S
Molecular Weight 397.749
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
EXELDERM

Approved Use

EXELDERM (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 Date

6.0462721E11
Curative
EXELDERM

Approved Use

EXELDERM (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 Date

6.0462721E11
Curative
EXELDERM

Approved Use

EXELDERM (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 Date

6.0462721E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.81 μg/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Doses

DosePopulationAdverse events​
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
Pruritus
Sources: Page: RS 44872
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
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
Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay.
2002 Aug
Topical antifungal treatment cures exit-site fungal infection.
2002 Oct
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
2003 Oct 9
Chiral separation by capillary electrophoresis using polysaccharides.
2004
EpoK, a cytochrome P450 involved in biosynthesis of the anticancer agents epothilones A and B. Substrate-mediated rescue of a P450 enzyme.
2004 Nov 23
Rapid method development for chiral separation in drug discovery using multi-column parallel screening and circular dichroism signal pooling.
2004 Sep 17
Inhibition of the enzymatic activity of heme oxygenases by azole-based antifungal drugs.
2006 Oct
Molecular properties of econazole and sulconazole relevant to bioavailability.
2006 Sep-Oct
Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration.
2007 Aug
Genome-wide fitness test and mechanism-of-action studies of inhibitory compounds in Candida albicans.
2007 Jun
Enantiomeric separation of several antimycotic azole drugs using supercritical fluid chromatography.
2007 Mar 16
1-[2-(2,4-Dichloro-benz-yloxy)-2-phenyl-ethyl]-1H-1,2,4-triazole.
2008 Nov 29
1-[2-(4-Bromo-benz-yloxy)-2-phenyl-ethyl]-1H-1,2,4-triazole.
2008 Sep 13
1-[2-(2,6-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-1,2,4-triazole.
2009 Dec 12
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009 Feb
Ultra-high concentration of amylose for chiral separations in capillary electrophoresis.
2009 Feb 27
Characterizing metabolic inhibition using electrochemical enzyme/DNA biosensors.
2009 Jan 15
Enantioselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea organocatalysis.
2009 Jul 1
1-[2-(2,4-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-1,2,4-triazole.
2009 Oct 28
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
Systematic analysis of genome-wide fitness data in yeast reveals novel gene function and drug action.
2010
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
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
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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:32:37 UTC 2023
Edited
by admin
on Fri Dec 15 18:32:37 UTC 2023
Record UNII
5D9HAA5Q5S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULCONAZOLE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
1H-IMIDAZOLE, 1-(2-(((4-CHLOROPHENYL)METHYL)THIO)-2-(2,4-DICHLOROPHENYL)ETHYL)-, (±)-
Systematic Name English
1-(2-(((4-CHLOROPHENYL)METHYL)THIO)-2-(2,4-DICHLOROPHENYL)ETHYL)-1H-IMIDAZOLE
Systematic Name English
1H-IMIDAZOLE, 1-(2-(((4-CHLOROPHENYL)METHYL)THIO)-2-(2,4-DICHLOROPHENYL)ETHYL)-
Systematic Name English
SULCONAZOLE [VANDF]
Common Name English
sulconazole [INN]
Common Name English
Sulconazole [WHO-DD]
Common Name English
(±)-SULCONAZOLE
Common Name English
SULCONAZOLE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC D01AC09
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
NDF-RT N0000008217
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
WHO-VATC QD01AC09
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
NDF-RT N0000175487
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
Code System Code Type Description
DRUG BANK
DB06820
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID8044129
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1221
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
CAS
59293-81-1
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
SUPERSEDED
CAS
61318-90-9
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
CAS
92446-60-1
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
SUPERSEDED
NCI_THESAURUS
C61958
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
LACTMED
Sulconazole
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
MERCK INDEX
m10295
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY Merck Index
CHEBI
9325
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
DRUG CENTRAL
2495
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
FDA UNII
5D9HAA5Q5S
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
PUBCHEM
5318
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
WIKIPEDIA
SULCONAZOLE
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
MESH
C033308
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
SMS_ID
100000083258
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
RXCUI
37319
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY RxNorm
INN
4332
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
DAILYMED
5D9HAA5Q5S
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
EVMPD
SUB10681MIG
Created by admin on Fri Dec 15 18:32:37 UTC 2023 , Edited by admin on Fri Dec 15 18:32:37 UTC 2023
PRIMARY
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