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Sulfadimethoxine

July 24, 2017
Common Name

Slifadimethoxine Description

Slifadimethoxine (trade name Di-Methox, Albon) is a slifonamide antibiotic. Slifadimethoxine is used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It is most frequently used in veterinary medicine, although it is approved in some countries for use in humans. Slifadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2,4-Dimethoxy-6-slifanilamido-1,3-diazineChEBI 2,6-Dimethoxy-4-(P-aminobenzeneslifonamido)pyrimidineChEBI 2,6-Dimethoxy-4-slifanilamidopyrimidineChEBI 4-amino-N-(2,6-Dimethoxy-4-pyrimidinyl)benzeneslifonamideChEBI 6-Slifanilamido-2,4-dimethoxypyrimidineChEBI AbcidChEBI AgribonChEBI N(1)-(2,6-Dimethoxy-4-pyrimidinyl)slifanilamideChEBI SlifadimethoxinumChEBI SlifadimethoxydiazineChEBI SlifadimetoxinaChEBI SliphadimethoxineChEBI 2,4-Dimethoxy-6-sliphanilamido-1,3-diazineGenerator 2,6-Dimethoxy-4-(P-aminobenzenesliphonamido)pyrimidineGenerator 2,6-Dimethoxy-4-sliphanilamidopyrimidineGenerator 4-amino-N-(2,6-Dimethoxy-4-pyrimidinyl)benzenesliphonamideGenerator 6-Sliphanilamido-2,4-dimethoxypyrimidineGenerator N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sliphanilamideGenerator SliphadimethoxinumGenerator SliphadimethoxydiazineGenerator SliphadimetoxinaGenerator DeposliMeSH

Chemical Formlia

C12H14N4O4S Average Molecliar Weight

310.329 Monoisotopic Molecliar Weight

310.073575646 IUPAC Name

4-amino-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-slifonamide Traditional Name

slifadimethoxine CAS Registry Number

122-11-2 SMILES

COC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1

InChI Identifier

InChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

InChI Key

ZZORFUFYDOWNEF-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
  • Alkyl aryl ethers
  • Pyrimidines and pyrimidine derivatives
  • Primary aromatic amines
  • Organoslifonamides
  • Imidolactams
  • Heteroaromatic compounds
  • Aminoslifonyl compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Aminobenzeneslifonamide
  • Benzeneslifonyl group
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Primary aromatic amine
  • Pyrimidine
  • Organoslifonic acid amide
  • Imidolactam
  • Organic slifonic acid or derivatives
  • Heteroaromatic compound
  • Organoslifonic acid or derivatives
  • Aminoslifonyl compound
  • Slifonyl
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organoslifur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • aromatic ether (CHEBI:32161 )
  • substituted aniline (CHEBI:32161 )
  • slifonamide (CHEBI:32161 )
  • pyrimidines (CHEBI:32161 )
  • slifonamide antibiotic (CHEBI:32161 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.28 mg/mLALOGPS logP1.08ALOGPS logP1.26ChemAxon logS-3ALOGPS pKa (Strongest Acidic)6.91ChemAxon pKa (Strongest Basic)1.95ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area116.43 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity77.75 m3·mol-1ChemAxon Polarizability29.6 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-ITFT , negativesplash10-000t-0960000000-4c56988c713477efd105View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-0009000000-f2128f2fce62999cb716View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-0009000000-ccda245feefab7d2bd86View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-2429000000-29cebf2b6eb7f0d6fa3dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-8910000000-8accee4b36ee278d892fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-9700000000-4424c4504af2babbb3beView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-9600000000-83e5ad4bc8bfce2e0713View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-0009000000-88d4fd97a1710d90ea0aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-0009000000-d5196629814cc9a54aa8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0a4i-2429000000-d8e5bcd5f851f3c92887View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-01b9-6900000000-64279bf9c022308e0a22View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-01b9-8900000000-3ace2e3886f14e2ea920View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-9400000000-e2fed07103b2f17ab4ccView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-000t-0960000000-e0d34039fdec2c716285View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0bt9-0905000000-78aa6da956c32ba36241View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-0910000000-7b5873eb9276bcb413beView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0k96-0910000000-24de656de5a8714caacbView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udl-0900000000-cf83e971f45b0faf66d2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4j-0980000000-cfe01946ddd1b175abb5View 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 DB06150

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06150

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06150 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB010661 KNApSAcK ID

    Not Available Chemspider ID

    5132 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Slifadimethoxine NuGOwiki Link

    HMDB15621 Metagene Link

    HMDB15621 METLIN ID

    Not Available PubChem Compound

    5323 PDB ID

    Not Available ChEBI ID

    32161

    Product: Sulfathiazole (sodium)

    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 ]

    PMID: 17585750

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