Identification

Name
Sulconazole
Accession Number
DB06820
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
RS-44872
Product Ingredients
IngredientUNIICASInChI Key
Sulconazole nitrate1T89100D5U61318-91-0CRKGMGQUHDNAPB-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ExeldermSolution10 mg/mLTopicalRanbaxy Inc.2009-04-08Not applicableUs
ExeldermCream10 mg/gTopicalRanbaxy Inc.2010-02-01Not applicableUs
Categories
UNII
5D9HAA5Q5S
CAS number
61318-90-9
Weight
Average: 397.74
Monoisotopic: 396.0021528
Chemical Formula
C18H15Cl3N2S
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

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).

Structured Indications
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
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.

Affected organisms
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Sulconazole.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Sulconazole is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Sulconazole is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Sulconazole is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Sulconazole is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Sulconazole.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Sulconazole.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Caroverine.Experimental
CerivastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Cerivastatin.Withdrawn
CilnidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Sulconazole.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Sulconazole.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Sulconazole.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Sulconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Sulconazole is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Sulconazole.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Sulconazole.Approved
DotarizineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Sulconazole is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Sulconazole.Approved
FelodipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Fendiline.Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Sulconazole.Approved
FlunarizineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Flunarizine.Approved
FluvastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Sulconazole can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Sulconazole is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Sulconazole.Approved
LovastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Lovastatin.Approved, Investigational
Magnesium SulfateThe risk or severity of adverse effects can be increased when Sulconazole is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Manidipine.Approved, Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Sulconazole.Approved, Investigational
MevastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Mevastatin.Experimental
MibefradilThe risk or severity of adverse effects can be increased when Sulconazole is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Sulconazole is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Nitrendipine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Sulconazole is combined with Otilonium.Experimental, Investigational
PerhexilineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Perhexiline.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Sulconazole.Approved, Vet Approved
PimozideSulconazole may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Sulconazole is combined with Pinaverium.Approved
PitavastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Pitavastatin.Approved
PravastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Pravastatin.Approved
PregabalinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Sulconazole.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Sulconazole.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Sulconazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Sulconazole.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Sulconazole.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Sulconazole.Approved
RisedronateThe risk or severity of adverse effects can be increased when Sulconazole is combined with Risedronate.Approved, Investigational
RosuvastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Rosuvastatin.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Sulconazole is combined with Simvastatin.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Sulconazole.Approved
SucralfateSucralfate can cause a decrease in the absorption of Sulconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Sulconazole.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Sulconazole.Approved, Investigational
TerodilineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Tetrahydropalmatine.Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Sulconazole.Approved, Withdrawn
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Sulconazole.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Sulconazole is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Sulconazole is combined with Tranilast.Approved, Investigational
UbidecarenoneThe risk or severity of adverse effects can be increased when Sulconazole is combined with Ubidecarenone.Approved, Experimental
VerapamilThe risk or severity of adverse effects can be increased when Sulconazole is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Sulconazole is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Sulconazole is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Sulconazole.Approved
Food Interactions
No interactions found.

References

General References
  1. Franz TJ, Lehman P: Percutaneous absorption of sulconazole nitrate in humans. J Pharm Sci. 1988 Jun;77(6):489-91. [PubMed:3171926]
  2. Holt RJ: Topical pharmacology of imidazole antifungals. J Cutan Pathol. 1976;3(1):45-59. [PubMed:945306]
External Links
KEGG Drug
D08535
KEGG Compound
C08076
PubChem Compound
5318
PubChem Substance
310264896
ChemSpider
5127
BindingDB
31770
ChEBI
77776
ChEMBL
CHEMBL1221
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulconazole
ATC Codes
D01AC09 — Sulconazole
FDA label
Download (56.7 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical10 mg/g
SolutionTopical10 mg/mL
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

Taxonomy

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 / Aryl chloride / Aryl halide / N-substituted imidazole / Azole / Heteroaromatic compound / Imidazole / Azacycle / Organoheterocyclic compound / Dialkylthioether
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, organic sulfide, dichlorobenzene, monochlorobenzenes (CHEBI:77776)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. [PubMed:11854151]
Kind
Protein
Organism
Human
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. [PubMed:11854151]
Kind
Protein
Organism
Human
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 10:21 / Updated on November 09, 2017 03:56