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.6,7 Sulconazole appears to be effective and well-tolerated in the treatment of superficial fungal infections.4
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulconazole (DB06820)
- 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).6,7
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Tinea corporis •••••••••••• •••••• •••••••• Treatment of Tinea cruris •••••••••••• •••••• •••••••• Treatment of Tinea pedis •••••••••••• ••••• Treatment of Tinea versicolor •••••••••••• •••••• •••••••• - Contraindications & Blackbox Warnings
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Sulconazole is a broad-spectrum antifungal that inhibits the growth of dermatophytes, yeasts and other filamentous and dimorphic fungi. The relative inhibition factor (RIF), a measurement that represents a fixed portion of the antigungal dose-response curve, can be determined to measure the inhibitory activity of antifungal drugs. Against pathogenic yeasts such as dermatophytes and Aspergilli, sulconazole had similar RIF values compared to other imidazoles.4 In in vitro conditions, the fungicidal potency of sulconazole depends on its concentration and the growth phase of the inoculum cells. Sulconazole has also shown antibacterial properties in vitro, with inhibitory concentrations (MICs) under 12.5 mg/L against several Staphylococcus species, as well as Streptococcus faecalis and several Gram-positive anaerobes.4
- Mechanism of action
The mechanism of action of sulconazole is not well established; however, it is thought to be similar to other imidazole derivatives.2 The function of imidazoles can be attributed to their structural resemblance to purines essential to metabolism. Imidazoles inhibit lanosterol 14-alpha demethylase, a cytochrome P-450-dependent enzyme in fungi responsible for converting lanosterol to ergosterol. Since ergosterol is required to maintain the integrity of the fungi membrane, the inhibition of lanosterol 14-alpha demethylase leads to increased fungal cellular permeability. Therefore, the use of an imidazole such as sulconazole inhibits fungal growth.3,4
Target Actions Organism ALanosterol 14-alpha demethylase inhibitor- Absorption
A study done on healthy subjects given sulconazole 1% cream over a seven-day period, showed that the total percutaneous absorption of sulconazole after topical administration was 8.71-11.3% of the dose.1 Another study also done on healthy volunteers given 1 g of sulconazole 1% cream, estimated that about 12% of the dose was absorbed through the skin.4 In general, topical imidazoles are poorly absorbed (<15%); however, sulconazole may have higher levels of absorption compared to others.1,5
- 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.1
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.6,7
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareClozapine The serum concentration of Clozapine can be increased when it is combined with Sulconazole. Doxorubicin The serum concentration of Doxorubicin can be increased when it is combined with Sulconazole. Fezolinetant The serum concentration of Fezolinetant can be increased when it is combined with Sulconazole. Haloperidol The serum concentration of Haloperidol can be increased when it is combined with Sulconazole. Lisdexamfetamine The serum concentration of dextroamphetamine, an active metabolite of Lisdexamfetamine, can be increased when used in combination with Sulconazole. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sulconazole nitrate 1T89100D5U 61318-91-0 CRKGMGQUHDNAPB-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Exelderm Cream 10 mg/1g Topical Physicians Total Care, Inc. 1989-02-28 2002-06-30 US 
Exelderm Solution 10 mg/1mL Topical Sun Pharmaceutical Industries, Inc. 2009-04-08 2020-06-30 US Exelderm Cream 10 mg/1g Topical Bristol Myers Squibb Pharma Company 2008-01-01 2008-10-31 US Exelderm Solution 10 mg/1mL Topical Journey Medical Corporation 2019-06-07 Not applicable US Exelderm Cream 10 mg/1g Topical Sun Pharmaceutical Industries Limited 2010-02-01 Not applicable US
Categories
- ATC Codes
- D01AC09 — Sulconazole
- Drug Categories
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Imidazole and Triazole Derivatives
- 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
- Franz TJ, Lehman P: Percutaneous absorption of sulconazole nitrate in humans. J Pharm Sci. 1988 Jun;77(6):489-91. [Article]
- Holt RJ: Topical pharmacology of imidazole antifungals. J Cutan Pathol. 1976;3(1):45-59. [Article]
- Mazu TK, Bricker BA, Flores-Rozas H, Ablordeppey SY: The Mechanistic Targets of Antifungal Agents: An Overview. Mini Rev Med Chem. 2016;16(7):555-78. [Article]
- Benfield P, Clissold SP: Sulconazole. A review of its antimicrobial activity and therapeutic use in superficial dermatomycoses. Drugs. 1988 Feb;35(2):143-53. doi: 10.2165/00003495-198835020-00004. [Article]
- Cleary JD, Taylor JW, Chapman SW: Imidazoles and triazoles in antifungal therapy. DICP. 1990 Feb;24(2):148-52. doi: 10.1177/106002809002400207. [Article]
- FDA Approved Drug Products: Exelderm (sulconazole nitrate) cream 1.0% tor topical use [Link]
- FDA Approved Drug Products: Exelderm (sulconazole nitrate) solution 1.0% for topical use [Link]
- External Links
- Human Metabolome Database
- HMDB0258569
- KEGG Drug
- D08535
- KEGG Compound
- C08076
- PubChem Compound
- 5318
- PubChem Substance
- 310264896
- ChemSpider
- 5127
- BindingDB
- 31770
- 37319
- ChEBI
- 77776
- ChEMBL
- CHEMBL1221
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulconazole
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 10 mg/1g Solution Topical 10 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 130ºC FDA label water solubility Slightly soluble FDA label - Predicted Properties
Property Value Source Water Solubility 0.00129 mg/mL ALOGPS logP 5.72 ALOGPS logP 6.06 Chemaxon logS -5.5 ALOGPS pKa (Strongest Basic) 6.78 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.82 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 104.37 m3·mol-1 Chemaxon Polarizability 39.57 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004u-2691000000-898b6e02c53a85cf5dee Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0209000000-da2b4f09175685b65fea Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-2915000000-e4d58d4d5b36961841c5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1905000000-a6f161becd4b236f1ab3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-7950000000-67448ae8085d01a1aaf6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ftf-4961000000-b805718493ef98fd5a81 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-5b64d00549ff594fb819 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.49037 predictedDeepCCS 1.0 (2019) [M+H]+ 190.1186 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.45457 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Precise mechanism unknown, but assumed to be similar to other imidazoles.
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol (By similarity).
- Gene Name
- ERG11
- Uniprot ID
- P50859
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 61304.95 Da
References
- Mazu TK, Bricker BA, Flores-Rozas H, Ablordeppey SY: The Mechanistic Targets of Antifungal Agents: An Overview. Mini Rev Med Chem. 2016;16(7):555-78. [Article]
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
- 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
- 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 at September 14, 2010 16:21 / Updated at February 02, 2024 22:53