Sulconazole

Identification

Summary

Sulconazole is a topical antifungal agent used for the treatment of tinea cruris, tinea corporis, and tinea versicolor caused by susceptible fungal strains.

Brand Names
Exelderm
Generic Name
Sulconazole
DrugBank Accession Number
DB06820
Background

Sulconazole, brand name Exelderm, is a broad-spectrum anti-fungal agent available as a topical cream and solution. Sulconazole nitrate, the active ingredient, is an imidazole derivative that inhibits the growth of common pathogenic dermatophytes making it an effective treatment for tinea cruris and tinea corporis infections.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 397.74
Monoisotopic: 396.0021528
Chemical Formula
C18H15Cl3N2S
Synonyms
  • Sulconazole
External IDs
  • RS-44872

Pharmacology

Indication

Sulconazole solution 1.0% is indicated for the treatment of tinea cruris and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum, and Microsporum canis; and for the treatment of tinea versicolor. Effectiveness has not been proven in tinea pedis (athlete’s foot).

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

The function of imidazole derivatives can be attributed to their structural resemblance to purines essential to metabolism.

Mechanism of action
Not Available
Absorption

Total sulconazole systemic absorption after topical administration was ~8.71% of the dose.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

About 6.70% of the dose was recovered in urine, and 2.01% in feces over a 7 day collection period. Radioactivity could be detected in both urine and feces at 7 days potentially due to a reservoir effect.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Sulconazole has been shown to be embryotoxic in a study of rats given 125 times the human dose (in mg/kg) and also resulted in prolonged gestation and dystocia. There are no adequate or controlled studies in pregnant women, therefore sulconazole should only be used during pregnancy if potential benefit justifies potential risk to the fetus.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Sulconazole.
OliceridineThe serum concentration of Oliceridine can be increased when it is combined with Sulconazole.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Sulconazole nitrate1T89100D5U61318-91-0CRKGMGQUHDNAPB-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ExeldermSolution10 mg/1mLTopicalSun Pharmaceutical Industries, Inc.2009-04-082020-06-30US flag
ExeldermCream10 mg/1gTopicalBristol Myers Squibb Pharma Company2008-01-012008-10-31US flag
ExeldermSolution10 mg/1mLTopicalJourney Medical Corporation2019-06-07Not applicableUS flag
ExeldermCream10 mg/1gTopicalSun Pharmaceutical Industries Limited2010-02-01Not applicableUS flag
ExeldermSolution10 mg/1mLTopicalBristol Myers Squibb Pharma Company2008-01-012008-10-31US flag
ExeldermCream10 mg/1gTopicalJourney Medical Corporation2019-06-07Not applicableUS flag
ExeldermCream10 mg/1gTopicalPhysicians Total Care, Inc.1989-02-282002-06-30US flag
Sulconazole NitrateSolution10 mg/1mLTopicalJg Pharma Inc.2020-02-24Not applicableUS flag
Sulconazole NitrateCream10 mg/1gTopicalJG Pharma2020-02-04Not applicableUS flag

Categories

ATC Codes
D01AC09 — Sulconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Dichlorobenzenes
Alternative Parents
N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Sulfenyl compounds / Dialkylthioethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, organic sulfide, dichlorobenzene, monochlorobenzenes (CHEBI:77776)
Affected organisms
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton

Chemical Identifiers

UNII
5D9HAA5Q5S
CAS number
61318-90-9
InChI Key
AFNXATANNDIXLG-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(2-{[(4-chlorophenyl)methyl]sulfanyl}-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
SMILES
ClC1=CC=C(CSC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

References

General References
  1. Franz TJ, Lehman P: Percutaneous absorption of sulconazole nitrate in humans. J Pharm Sci. 1988 Jun;77(6):489-91. [Article]
  2. Holt RJ: Topical pharmacology of imidazole antifungals. J Cutan Pathol. 1976;3(1):45-59. [Article]
KEGG Drug
D08535
KEGG Compound
C08076
PubChem Compound
5318
PubChem Substance
310264896
ChemSpider
5127
BindingDB
31770
RxNav
37319
ChEBI
77776
ChEMBL
CHEMBL1221
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulconazole
FDA label
Download (56.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical10 mg/1g
SolutionTopical10 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00129 mg/mLALOGPS
logP5.72ALOGPS
logP6.06ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.37 m3·mol-1ChemAxon
Polarizability39.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data limited to in vitro studies.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da

Drug created on September 14, 2010 16:21 / Updated on May 07, 2021 21:43