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Identification
NameButoconazole
Accession NumberDB00639  (APRD00834)
TypeSmall Molecule
GroupsApproved
Description

Butoconazole is an imidazole antifungal used in gynecology.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazoleNot AvailableNot Available
Alant starchNot AvailableIS
ButoconazolGerman/SpanishINN
ButoconazoleFrenchINN
ButoconazolumLatinINN
CompositenstärkeNot AvailableIS
DahlinNot AvailableIS
PolyfructosanumNot AvailableIS
Salts
Name/CAS Structure Properties
Butoconazole nitrate
Thumb Not applicable DBSALT001012
Brand names
NameCompany
FemstatBayer
Femstat 3Bayer
GynazolGedeon Richter
GynazoleOM
Gynazole-1Ferring
GynofortGedeon Richter
GynomykWill
InuleadFuji Yakuhin
Mycelex-3Bayer
VolusolFarmindustria
Brand mixturesNot Available
Categories
CAS number64872-77-1
WeightAverage: 411.776
Monoisotopic: 410.017802365
Chemical FormulaC19H17Cl3N2S
InChI KeySWLMUYACZKCSHZ-UHFFFAOYSA-N
InChI
InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2
IUPAC Name
1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole
SMILES
ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassHalobenzenes
Direct parentDichlorobenzenes
Alternative parentsAryl Chlorides; N-substituted Imidazoles; Thioethers; Polyamines; Organochlorides
Substituentsaryl chloride; aryl halide; n-substituted imidazole; azole; imidazole; polyamine; thioether; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
Pharmacology
IndicationFor the local treatment of vulvovaginal candidiasis (infections caused by Candida)
PharmacodynamicsButoconazole is an imidazole derivative that has fungicidal activity in vitro against Candida spp. and has been demonstrated to be clinically effective against vaginal infections due to Candida albicans. Candida albicans has been identified as the predominant species responsible for vulvovaginal candidasis.
Mechanism of actionThe exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell.
AbsorptionFollowing vaginal administration of butoconazole nitrate vaginal cream, 2% to 3 women, 1.7% (range 1.3-2.2%) of the dose was absorbed on average.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat: LD50 = >1720 mg/kg.
Affected organisms
  • Fungi, yeast and protozoans
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9258
Blood Brain Barrier + 0.9716
Caco-2 permeable + 0.6035
P-glycoprotein substrate Non-substrate 0.6398
P-glycoprotein inhibitor I Non-inhibitor 0.6239
P-glycoprotein inhibitor II Inhibitor 0.6822
Renal organic cation transporter Inhibitor 0.7157
CYP450 2C9 substrate Non-substrate 0.7714
CYP450 2D6 substrate Non-substrate 0.8601
CYP450 3A4 substrate Non-substrate 0.6941
CYP450 1A2 substrate Inhibitor 0.934
CYP450 2C9 substrate Inhibitor 0.8949
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate Inhibitor 0.8365
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9896
Ames test Non AMES toxic 0.7381
Carcinogenicity Non-carcinogens 0.9223
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.0919 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.792
hERG inhibition (predictor II) Inhibitor 0.8263
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Bayer healthcare llc
  • Kv pharmaceutical co
Packagers
Dosage forms
FormRouteStrength
CreamIntravaginal
Prices
Unit descriptionCostUnit
Gynazole-1 cream10.89USDg
Femstat 3 cream0.96USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States59938561997-11-172017-11-17
United States52663291993-11-302010-11-30
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point~159°C with decomposition (nitrate salt)Not Available
water solubilityNitrate salt: 0.26 mg/ml (practically insoluble)Not Available
logP6.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000818ALOGPS
logP6.7ALOGPS
logP6.55ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.99 m3·mol-1ChemAxon
Polarizability41.01 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Laszlo Czibula, Laszlo Dobay, Eva Werkne Papp, Judit Nagyne Bagdy, Ferenc Sebok, “High Purity Butoconazole Nitrate with Specified Particle Size and a Process for the Preparation Thereof.” U.S. Patent US20080221190, issued September 11, 2008.

US20080221190
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00880
KEGG CompoundC08066
PubChem Compound47472
PubChem Substance46508016
ChemSpider43192
Therapeutic Targets DatabaseDAP001267
PharmGKBPA164781353
Drug Product Database2248417
RxListhttp://www.rxlist.com/cgi/generic2/butoconazole.htm
Drugs.comhttp://www.drugs.com/cdi/butoconazole-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/myc1567.shtml
WikipediaButoconazole
ATC CodesG01AF15
AHFS Codes
  • 84:04.08.08
PDB EntriesNot Available
FDA labelshow(4.11 MB)
MSDSshow(81.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Ergosterol

Kind: small molecule

Organism: Candida albicans

Pharmacological action: yes

Actions: other

Components

Name UniProt ID Details

References:

  1. Pfaller MA, Riley J, Koerner T: Effects of terconazole and other azole antifungal agents on the sterol and carbohydrate composition of Candida albicans. Diagn Microbiol Infect Dis. 1990 Jan-Feb;13(1):31-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 16, 2014 15:16