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/mLTopicalSun Pharmaceutical Industries Limited2009-04-08Not applicableUs
ExeldermCream10 mg/gTopicalSun Pharmaceutical Industries Limited2010-02-01Not 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).

Associated Conditions
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
AgmatineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Sulconazole.Approved, Investigational
AmrinoneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Aranidipine.Approved, Investigational
AtorvastatinThe risk or severity of myopathy can be increased when Sulconazole is combined with Atorvastatin.Approved
AzelnidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Sulconazole can be increased when used in combination with Bioallethrin.Approved, Experimental
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 therapeutic efficacy of Sulconazole can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Sulconazole.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Sulconazole can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Sulconazole.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Sulconazole can be increased when used in combination 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 therapeutic efficacy of Sulconazole can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Sulconazole.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Sulconazole.Approved, Investigational
DotarizineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Sulconazole.Approved
FelodipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Fendiline.Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Sulconazole.Approved
Fish oilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Sulconazole can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Sulconazole can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Sulconazole can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Sulconazole.Approved
Magnesium sulfateThe therapeutic efficacy of Sulconazole can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Sulconazole can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Methsuximide.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Sulconazole.Approved, Investigational
MibefradilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Sulconazole can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Sulconazole can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Sulconazole.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Sulconazole can be increased when used in combination with Pinaverium.Approved
PitolisantThe serum concentration of Pitolisant can be increased when it is combined with Sulconazole.Approved, Investigational
PrenylamineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Sulconazole.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Sulconazole.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Sulconazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Sulconazole.Approved, Investigational
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, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Sulconazole.Approved, Investigational
SeletracetamThe therapeutic efficacy of Sulconazole can be increased when used in combination with Seletracetam.Investigational
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 therapeutic efficacy of Sulconazole can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Sulconazole can be increased when used in combination 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, Investigational
Tolfenamic AcidThe therapeutic efficacy of Sulconazole can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Sulconazole can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Sulconazole can be increased when used in combination with Trimethadione.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Sulconazole.Approved
VerapamilThe therapeutic efficacy of Sulconazole can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Sulconazole can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Sulconazole can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Sulconazole.Approved
ZonisamideThe therapeutic efficacy of Sulconazole can be increased when used in combination with Zonisamide.Approved, Investigational
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 June 09, 2018 04:16