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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
FemstatBayer
Femstat 3Bayer
GynazolGedeon Richter
GynazoleOM
Gynazole-1Ferring
GynofortGedeon Richter
GynomykWill
InuleadFuji Yakuhin
Mycelex-3Bayer
VolusolFarmindustria
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Butoconazole nitrate
ThumbNot applicableDBSALT001012
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Thiophenol ether
  • 1,3-dichlorobenzene
  • Alkylarylthioether
  • Halobenzene
  • Chlorobenzene
  • N-substituted imidazole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9258
Blood Brain Barrier+0.9716
Caco-2 permeable+0.6035
P-glycoprotein substrateNon-substrate0.6398
P-glycoprotein inhibitor INon-inhibitor0.6239
P-glycoprotein inhibitor IIInhibitor0.6822
Renal organic cation transporterInhibitor0.7157
CYP450 2C9 substrateNon-substrate0.7714
CYP450 2D6 substrateNon-substrate0.8601
CYP450 3A4 substrateNon-substrate0.6941
CYP450 1A2 substrateInhibitor0.934
CYP450 2C9 substrateInhibitor0.8949
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateInhibitor0.8365
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9896
Ames testNon AMES toxic0.7381
CarcinogenicityNon-carcinogens0.9223
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.0919 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.792
hERG inhibition (predictor II)Inhibitor0.8263
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Bayer healthcare llc
  • Kv pharmaceutical co
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Gynazole-1 cream10.89USD g
Femstat 3 cream0.96USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States52663291993-11-302010-11-30
United States59938561997-11-172017-11-17
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 Solubility0.000818 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesG01AF15
AHFS Codes
  • 84:04.08.08
PDB EntriesNot Available
FDA labelDownload (4.11 MB)
MSDSDownload (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