Butoconazole

Identification

Summary

Butoconazole is an imidazole antifungal used to treat vulvovaginal candidiasis.

Brand Names
Gynazole-1
Generic Name
Butoconazole
DrugBank Accession Number
DB00639
Background

Butoconazole is an imidazole antifungal used in gynecology.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 411.776
Monoisotopic: 410.017802365
Chemical Formula
C19H17Cl3N2S
Synonyms
  • 1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazole
  • Butoconazol
  • Butoconazole
  • Butoconazolum
External IDs
  • RS 35887
  • RS 35887-00-10-3
  • RS 35887-10-3

Pharmacology

Indication

For the local treatment of vulvovaginal candidiasis (infections caused by Candida)

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Butoconazole 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 action

The 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.

TargetActionsOrganism
AErgosterol
other
Candida albicans
Absorption

Following 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 distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Oral, rat: LD50 = >1720 mg/kg.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Butoconazole nitrate4805237NP564872-77-1ZHPWRQIPPNZNML-UHFFFAOYSA-N
International/Other Brands
Femstat (Bayer) / Femstat 3 (Bayer) / Gynazol (Gedeon Richter) / Gynazole (OM) / Gynofort (Gedeon Richter) / Gynomyk (Will) / Inulead (Fuji Yakuhin) / Mycelex-3 (Bayer) / Volusol (Farmindustria)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gynazole-1Cream20 mg/1gVaginalTher Rx Corporation2009-11-232011-06-30US flag
Gynazole-1Cream20 mg/1gVaginalPhysicians Total Care, Inc.2003-06-302008-06-30US flag
Gynazole.1Cream2 %VaginalFerring Pharmaceuticals2004-04-202014-01-15Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gynazole 1Cream100 mg/5gVaginalPerrigo New York Inc2015-04-29Not applicableUS flag
Gynazole 1Cream100 mg/5gVaginalAmag Pharmaceuticals Inc2012-12-272016-10-01US flag

Categories

ATC Codes
G01AF20 — Combinations of imidazole derivativesG01AF15 — Butoconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Thiophenol ethers / Dichlorobenzenes / Alkylarylthioethers / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
1,3-dichlorobenzene / Alkylarylthioether / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Aryl thioether / Azacycle / Azole / Chlorobenzene / Halobenzene
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
conazole antifungal drug, aryl sulfide, imidazoles, imidazole antifungal drug, dichlorobenzene, monochlorobenzenes (CHEBI:3240)
Affected organisms
  • Fungi, yeast and protozoans

Chemical Identifiers

UNII
0Q771797PH
CAS number
64872-76-0
InChI Key
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

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 References
  1. FDA Approved Drug Products: Gynazole-1 (butoconazole nitrate) vaginal cream [Link]
Human Metabolome Database
HMDB0014777
KEGG Drug
D07598
KEGG Compound
C08065
PubChem Compound
47472
PubChem Substance
46508016
ChemSpider
43192
BindingDB
79206
RxNav
19884
ChEBI
3240
ChEMBL
CHEMBL1295
Therapeutic Targets Database
DAP001267
PharmGKB
PA164781353
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Butoconazole
FDA label
Download (4.11 MB)
MSDS
Download (81.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentVaginal Infections1
3CompletedTreatmentVaginal Inflammation / Vulvovaginitis1
2Not Yet RecruitingTreatmentVulvovaginal Candidiasis1
Not AvailableCompletedTreatmentVulvovaginal Candidiasis1

Pharmacoeconomics

Manufacturers
  • Roche palo alto llc
  • Bayer healthcare llc
  • Kv pharmaceutical co
Packagers
  • A-S Medication Solutions LLC
  • Bayer Healthcare
  • KV Pharmaceutical Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Ther-Rx Corp.
Dosage Forms
FormRouteStrength
CreamVaginal100 mg/5g
CreamVaginal20 mg/1g
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)Region
US5266329No1993-11-302010-11-30US flag
US5993856No1999-11-302017-11-17US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)~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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)

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

Targets

Drugtargets2
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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. [Article]

Drug created on June 13, 2005 13:24 / Updated on August 13, 2021 04:43