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Sertaconazole

July 24, 2017
Common Name

Sertaconazole Description

Sertaconazole is only found in individuals that have used or taken this drug. Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athletes foot. [Wikipedia]Sertaconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis reslits in increased cellliar permeability causing leakage of cellliar contents. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source DemofixChEMBL ErtaczoChEMBL

Chemical Formlia

C20H15Cl3N2OS Average Molecliar Weight

437.77 Monoisotopic Molecliar Weight

435.997066923 IUPAC Name

1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole Traditional Name

sertaconazole CAS Registry Number

99592-32-2 SMILES

ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl

InChI Identifier

InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2

InChI Key

JLGKQTAYUIMGRK-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzothiophenes Direct Parent

1-benzothiophenes Alternative Parents

  • Benzylethers
  • Dichlorobenzenes
  • N-substituted imidazoles
  • Aryl chlorides
  • Thiophenes
  • Heteroaromatic compounds
  • Dialkyl ethers
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organochlorides
  • Hydrocarbon derivatives

    • Substituents

  • 1-benzothiophene
  • Benzylether
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Thiophene
  • Imidazole
  • Azacycle
  • Dialkyl ether
  • Ether
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • imidazoles (CHEBI:83682 )
  • 1-benzothiophenes (CHEBI:83682 )
  • ether (CHEBI:83682 )
  • dichlorobenzene (CHEBI:83682 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antifungal Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.37e-03 g/LNot Available LogP6.2Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0064 mg/mLALOGPS logP5.74ALOGPS logP6.23ChemAxon logS-4.8ALOGPS pKa (Strongest Basic)6.77ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area27.05 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity111.6 m3·mol-1ChemAxon Polarizability42.93 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01153

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01153

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01153 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    59273 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Sertaconazole NuGOwiki Link

    HMDB15284 Metagene Link

    HMDB15284 METLIN ID

    Not Available PubChem Compound

    65863 PDB ID

    Not Available ChEBI ID

    775147

    Product: DHBS

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4-dimethyl cholesta-8,14,24-triene-3-beta-ol.
    Gene Name:
    CYP51A1
    Uniprot ID:
    Q16850
    Molecular weight:
    57277.81
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 20735016

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