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Sulfaphenazole

July 24, 2017
Common Name

Slifaphenazole Description

Slifaphenazole is only found in individuals that have used or taken this drug. Slifaphenazole is a slifonamide antibacterial. In bacteria, antibacterial slifonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be “starved” of folate and die. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-Phenyl-5-slifanilamidopyrazoleChEBI 3-(P-Aminobenzeneslifonamido)-2-phenylpyrazoleChEBI 5-Slifanilamido-1-phenylpyrazoleChEBI N'-(1-phenylpyrazol-5-yl)slifanilamideChEBI N(1)-(1-Phenylpyrazol-5-yl)slifanilamideChEBI SlifabidChEBI SlifafenazolChEBI SlifaphenazolChEBI SlifaphenazolumChEBI SliphaphenazoleChEBI 1-Phenyl-5-sliphanilamidopyrazoleGenerator 3-(P-Aminobenzenesliphonamido)-2-phenylpyrazoleGenerator 5-Sliphanilamido-1-phenylpyrazoleGenerator N'-(1-phenylpyrazol-5-yl)sliphanilamideGenerator N(1)-(1-Phenylpyrazol-5-yl)sliphanilamideGenerator SliphabidGenerator SliphafenazolGenerator SliphaphenazolGenerator SliphaphenazolumGenerator PhenylslifapyrazoleHMDB SlifaphenazonHMDB SlifaphenylpipazolHMDB SlifaphenylpyrazolHMDB SlifaphenylpyrazoleHMDB SlifonylpyrazolHMDB SliphenazoleHMDB

Chemical Formlia

C15H14N4O2S Average Molecliar Weight

314.362 Monoisotopic Molecliar Weight

314.083746402 IUPAC Name

4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-slifonamide Traditional Name

merian CAS Registry Number

526-08-9 SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2

InChI Key

QWCJHSGMANYXCW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Azoles Direct Parent

Phenylpyrazoles Alternative Parents

  • Aminobenzeneslifonamides
  • Benzeneslifonyl compounds
  • Aniline and substituted anilines
  • Primary aromatic amines
  • Organoslifonamides
  • Heteroaromatic compounds
  • Aminoslifonyl compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Aminobenzeneslifonamide
  • Phenylpyrazole
  • Benzeneslifonamide
  • Benzeneslifonyl group
  • Aniline or substituted anilines
  • Monocyclic benzene moiety
  • Primary aromatic amine
  • Organoslifonic acid amide
  • Benzenoid
  • Organic slifonic acid or derivatives
  • Organoslifonic acid or derivatives
  • Heteroaromatic compound
  • Slifonyl
  • Aminoslifonyl compound
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organoslifur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • pyrazoles (CHEBI:77780 )
  • substituted aniline (CHEBI:77780 )
  • slifonamide (CHEBI:77780 )
  • primary amino compound (CHEBI:77780 )
  • slifonamide antibiotic (CHEBI:77780 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antibacterial Agents
  • Slifonamides

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point101 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP1.52HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.28 mg/mLALOGPS logP1.59ALOGPS logP1.81ChemAxon logS-3ALOGPS pKa (Strongest Acidic)6.9ChemAxon pKa (Strongest Basic)2.43ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area90.01 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity85.21 m3·mol-1ChemAxon Polarizability31.82 Å3ChemAxon Number of Rings3ChemAxon 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

  • Membrane

    • 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 DB06729

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06729

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06729 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

    5144 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Slifaphenazole NuGOwiki Link

    HMDB15667 Metagene Link

    HMDB15667 METLIN ID

    Not Available PubChem Compound

    5335 PDB ID

    Not Available ChEBI ID

    253330

    Product: Vanoxerine (dihydrochloride)

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

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    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 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
    Gene Name:
    CYP2D6
    Uniprot ID:
    P10635
    Molecular weight:
    55768.94
    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 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81
    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 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
    Gene Name:
    CYP2C8
    Uniprot ID:
    P10632
    Molecular weight:
    55824.275
    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 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
    Gene Name:
    CYP2A6
    Uniprot ID:
    P11509
    Molecular weight:
    56517.005
    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: 24292392

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