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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0014777
Secondary Accession Numbers
  • HMDB14777
Metabolite Identification
Common NameButoconazole
DescriptionButoconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal used in gynecology.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.
Structure
Data?1582753220
Synonyms
ValueSource
1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazoleChEBI
ButoconazolChEBI
ButoconazolumChEBI
GynofortKegg
1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulphanyl)-butyl]-1H-imidazoleGenerator
Butoconazole nitrateHMDB
Bayer brand 1 OF butoconazole nitrateHMDB
Mycelex-3HMDB
1-(4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-N-butyl)-1H-imidazoleHMDB
Bayer brand 2 OF butoconazole nitrateHMDB
GynomykHMDB
Ther-RX brand OF butoconazole nitrateHMDB
FemstalHMDB
Aventis brand OF butoconazole nitrateHMDB
FemstatHMDB
Gynazole-1HMDB
Syntex brand OF butoconazole nitrateHMDB
Will brand OF butoconazole nitrateHMDB
Chemical FormulaC19H17Cl3N2S
Average Molecular Weight411.776
Monoisotopic Molecular Weight410.017802365
IUPAC Name1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole
Traditional Namebutoconazole
CAS Registry Number64872-77-1
SMILES
ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1
InChI Identifier
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
InChI KeySWLMUYACZKCSHZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines 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
  • Aryl thioether
  • 1,3-dichlorobenzene
  • Thiophenol ether
  • Chlorobenzene
  • Alkylarylthioether
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point159 °C (decomposition)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.00082 g/LNot Available
LogP6.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
logP6.7ALOGPS
logP6.55ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.99 m³·mol⁻¹ChemAxon
Polarizability41.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-6921000000-df9fbb2ed1919d5db32d2017-08-28View Spectrum
MSMass Spectrum (Electron Ionization)splash10-003r-9811000000-60e5190210e7970a390b2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0291800000-175d20ae946894d63ff02017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-6966500000-99152c227089dc60fc642017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-6900000000-33b44a1350666f009c482017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1110900000-66f5c95ad320950db5ee2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9330100000-d4e9c87c57f1a3ccac9d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-7900000000-e6e65ee82f67ecda0db02017-07-26View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00639 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00639 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00639
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID43192
KEGG Compound IDC08065
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButoconazole
METLIN IDNot Available
PubChem Compound47472
PDB IDNot Available
ChEBI ID3240
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available