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Sulfamoxole

July 24, 2017
Common Name

Slifamoxole Description

Slifamoxole is only found in individuals that have used or taken this drug. It is a slifonamide antibacterial. Slifamoxole is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-(P-Aminobenzeneslifonamido)-4,5-dimethyloxazoleChEBI 2-(P-Aminobenzolslifonamido)-4,5-dimethyloxazolChEBI 4,5-Dimethyl-2-slifanilamidooxazoleChEBI 4-amino-N-(4,5-Dimethyl-2-oxazolyl)benzeneslifonamideChEBI N1-(4,5-Dimethyl-2-oxazolyl)slifanilamideChEBI OxaslifaChEBI P-Aminobenzeneslifonyl-2-amino-4,5-dimethyloxazoleChEBI SlifadimethyloxazoleChEBI SlifamoxolChEBI SlifamoxolumChEBI SliphamoxoleChEBI 2-(P-Aminobenzenesliphonamido)-4,5-dimethyloxazoleGenerator 2-(P-Aminobenzolsliphonamido)-4,5-dimethyloxazolGenerator 4,5-Dimethyl-2-sliphanilamidooxazoleGenerator 4-amino-N-(4,5-Dimethyl-2-oxazolyl)benzenesliphonamideGenerator N1-(4,5-Dimethyl-2-oxazolyl)sliphanilamideGenerator OxasliphaGenerator P-Aminobenzenesliphonyl-2-amino-4,5-dimethyloxazoleGenerator SliphadimethyloxazoleGenerator SliphamoxolGenerator SliphamoxolumGenerator SlifonoHMDB

Chemical Formlia

C11H13N3O3S Average Molecliar Weight

267.304 Monoisotopic Molecliar Weight

267.067761987 IUPAC Name

4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-slifonamide Traditional Name

slifamoxole CAS Registry Number

729-99-7 SMILES

CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1

InChI Identifier

InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)

InChI Key

CYFLXLSBHQBMFT-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as aminobenzeneslifonamides. These are organic compounds containing a benzeneslifonamide moiety with an amine group attached to the benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Aminobenzeneslifonamides Alternative Parents

  • Benzeneslifonyl compounds
  • Aniline and substituted anilines
  • 2,4,5-trisubstituted oxazoles
  • Primary aromatic amines
  • Organoslifonamides
  • Heteroaromatic compounds
  • Aminoslifonyl compounds
  • Oxacyclic compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Aminobenzeneslifonamide
  • Benzeneslifonyl group
  • 2,4,5-trisubstituted 1,3-oxazole
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Organoslifonic acid amide
  • Azole
  • Oxazole
  • Heteroaromatic compound
  • Organic slifonic acid or derivatives
  • Organoslifonic acid or derivatives
  • Aminoslifonyl compound
  • Slifonyl
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organoslifur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • slifonamide (CHEBI:55548 )
  • slifonamide antibiotic (CHEBI:55548 )
  • oxazole (CHEBI:55548 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antibacterial Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point185 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.27 mg/mLALOGPS logP1.04ALOGPS logP0.59ChemAxon logS-3ALOGPS pKa (Strongest Acidic)6.81ChemAxon pKa (Strongest Basic)1.94ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area98.22 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity67.51 m3·mol-1ChemAxon Polarizability27.44 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-3900000000-23eed4bc89bcf24079bdView in MoNA 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 DB08798

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08798

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08798 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

    12361 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Slifamoxole NuGOwiki Link

    HMDB15688 Metagene Link

    HMDB15688 METLIN ID

    Not Available PubChem Compound

    12894 PDB ID

    Not Available ChEBI ID

    55548

    Product: Triamterene

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [PubMed:13888264 ]

    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. Zweers-Zeilmaker WM, Horbach GJ, Witkamp RF: Differential inhibitory effects of phenytoin, diclofenac, phenylbutazone and a series of sulfonamides on hepatic cytochrome P4502C activity in vitro, and correlation with some molecular descriptors in the dwarf goat (Caprus hircus aegagrus). Xenobiotica. 1997 Aug;27(8):769-80. [PubMed:9293615 ]

    PMID: 24992374

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