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Identification
NameButoconazole
Accession NumberDB00639  (APRD00834)
TypeSmall Molecule
GroupsApproved
DescriptionButoconazole is an imidazole antifungal used in gynecology.
Structure
Thumb
Synonyms
Alant starch
Butoconazol
Butoconazole
Butoconazolum
Compositenstärke
Dahlin
Polyfructosanum
External Identifiers
  • RS 35887
  • RS 35887-00-10-3
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gynazole.1cream2 %vaginalFerring Inc2004-04-202014-01-15Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gynazole 1cream100 mg/5gvaginalPerrigo New York Inc2015-04-29Not applicableUs
Gynazole 1cream100 mg/5gvaginalLumara Health, Inc.2012-12-27Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
64872-77-1
ThumbNot applicableDBSALT001012
Categories
UNII0Q771797PH
CAS number64872-76-0
WeightAverage: 411.776
Monoisotopic: 410.017802365
Chemical FormulaC19H17Cl3N2S
InChI KeyInChIKey=SWLMUYACZKCSHZ-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.
Related Articles
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 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.8365
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Bayer healthcare llc
  • Kv pharmaceutical co
Packagers
Dosage forms
FormRouteStrength
Creamvaginal100 mg/5g
Creamvaginal2 %
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5266329 No1993-11-302010-11-30Us
US5993856 No1997-11-172017-11-17Us
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 ReferencesNot 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 Interactions
Drug
AmlodipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Amlodipine.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Butoconazole.
AmrinoneThe risk or severity of adverse effects can be increased when Butoconazole is combined with Amrinone.
AzelnidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Azelnidipine.
AzimilideThe risk or severity of adverse effects can be increased when Butoconazole is combined with Azimilide.
BarnidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Barnidipine.
BenidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Benidipine.
BepridilThe risk or severity of adverse effects can be increased when Butoconazole is combined with Bepridil.
BuspironeThe metabolism of Buspirone can be decreased when combined with Butoconazole.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Butoconazole.
CilnidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Cilnidipine.
CinnarizineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Cinnarizine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Butoconazole.
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Butoconazole.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Butoconazole.
DarodipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Darodipine.
DidanosineDidanosine can cause a decrease in the absorption of Butoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
DiltiazemThe risk or severity of adverse effects can be increased when Butoconazole is combined with Diltiazem.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Butoconazole.
DofetilideThe metabolism of Dofetilide can be decreased when combined with Butoconazole.
DotarizineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Dotarizine.
EfonidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Efonidipine.
EperisoneThe risk or severity of adverse effects can be increased when Butoconazole is combined with Eperisone.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Butoconazole.
FelodipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Felodipine.
FendilineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Fendiline.
FlunarizineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Flunarizine.
FosphenytoinThe serum concentration of Butoconazole can be decreased when it is combined with Fosphenytoin.
GabapentinThe risk or severity of adverse effects can be increased when Butoconazole is combined with Gabapentin.
IsradipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Isradipine.
LacidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Lacidipine.
LamotrigineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Lamotrigine.
LercanidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Lercanidipine.
LosartanThe metabolism of Losartan can be decreased when combined with Butoconazole.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Butoconazole is combined with Magnesium Sulfate.
ManidipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Manidipine.
MibefradilThe risk or severity of adverse effects can be increased when Butoconazole is combined with Mibefradil.
NicardipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nicardipine.
NifedipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nifedipine.
NiguldipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Niguldipine.
NiludipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Niludipine.
NilvadipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nilvadipine.
NimesulideThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nimesulide.
NimodipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nimodipine.
NisoldipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nisoldipine.
NitrendipineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Nitrendipine.
PerhexilineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Perhexiline.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Butoconazole.
PimozideButoconazole may increase the arrhythmogenic activities of Pimozide.
PinaveriumThe risk or severity of adverse effects can be increased when Butoconazole is combined with Pinaverium.
PregabalinThe risk or severity of adverse effects can be increased when Butoconazole is combined with Pregabalin.
PrenylamineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Prenylamine.
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Butoconazole.
QuinidineThe metabolism of Quinidine can be decreased when combined with Butoconazole.
RanolazineThe metabolism of Ranolazine can be decreased when combined with Butoconazole.
RisedronateThe risk or severity of adverse effects can be increased when Butoconazole is combined with Risedronate.
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Butoconazole.
SucralfateSucralfate can cause a decrease in the absorption of Butoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
SunitinibThe metabolism of Sunitinib can be decreased when combined with Butoconazole.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Butoconazole.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Butoconazole is combined with Tolfenamic Acid.
TranilastThe risk or severity of adverse effects can be increased when Butoconazole is combined with Tranilast.
VerapamilThe risk or severity of adverse effects can be increased when Butoconazole is combined with Verapamil.
XylometazolineThe risk or severity of adverse effects can be increased when Butoconazole is combined with Xylometazoline.
ZiconotideThe risk or severity of adverse effects can be increased when Butoconazole is combined with Ziconotide.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Butoconazole.
Food InteractionsNot Available

Targets

1. Ergosterol
Kind
Small molecule
Organism
Candida albicans
Pharmacological action
yes
Actions
other
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:2184984 ]
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Drug created on June 13, 2005 07:24 / Updated on September 26, 2016 02:12