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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:21:12 UTC
HMDB IDHMDB0015621
Secondary Accession Numbers
  • HMDB15621
Metabolite Identification
Common NameSulfadimethoxine
DescriptionSulfadimethoxine (trade name Di-Methox, Albon) is a sulfonamide antibiotic. Sulfadimethoxine 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. Sulfadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid.
Structure
Thumb
Synonyms
ValueSource
2,4-Dimethoxy-6-sulfanilamido-1,3-diazineChEBI
2,6-Dimethoxy-4-(P-aminobenzenesulfonamido)pyrimidineChEBI
2,6-Dimethoxy-4-sulfanilamidopyrimidineChEBI
4-amino-N-(2,6-Dimethoxy-4-pyrimidinyl)benzenesulfonamideChEBI
6-Sulfanilamido-2,4-dimethoxypyrimidineChEBI
AbcidChEBI
AgribonChEBI
N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamideChEBI
SulfadimethoxinumChEBI
SulfadimethoxydiazineChEBI
SulfadimetoxinaChEBI
SulphadimethoxineChEBI
2,4-Dimethoxy-6-sulphanilamido-1,3-diazineGenerator
2,6-Dimethoxy-4-(P-aminobenzenesulphonamido)pyrimidineGenerator
2,6-Dimethoxy-4-sulphanilamidopyrimidineGenerator
4-amino-N-(2,6-Dimethoxy-4-pyrimidinyl)benzenesulphonamideGenerator
6-Sulphanilamido-2,4-dimethoxypyrimidineGenerator
N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulphanilamideGenerator
SulphadimethoxinumGenerator
SulphadimethoxydiazineGenerator
SulphadimetoxinaGenerator
DeposulMeSH
Chemical FormulaC12H14N4O4S
Average Molecular Weight310.329
Monoisotopic Molecular Weight310.073575646
IUPAC Name4-amino-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
Traditional Namesulfadimethoxine
CAS Registry Number122-11-2
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 KeyZZORFUFYDOWNEF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Pyrimidine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Azacycle
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability29.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4950000000-007497762ea1c35c4e34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3910000000-0ac9853510aee4214006View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0960000000-4c56988c713477efd105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-f2128f2fce62999cb716View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-ccda245feefab7d2bd86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-2429000000-29cebf2b6eb7f0d6fa3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-8910000000-8accee4b36ee278d892fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9700000000-4424c4504af2babbb3beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9600000000-83e5ad4bc8bfce2e0713View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-88d4fd97a1710d90ea0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-d5196629814cc9a54aa8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-2429000000-d8e5bcd5f851f3c92887View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01b9-6900000000-64279bf9c022308e0a22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01b9-8900000000-3ace2e3886f14e2ea920View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9400000000-e2fed07103b2f17ab4ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0960000000-e0d34039fdec2c716285View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0009000000-6a816a27b2d84825241fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0905000000-78aa6da956c32ba36241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0910000000-7b5873eb9276bcb413beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0k96-0910000000-24de656de5a8714caacbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0329000000-144fa34c18dc427b2420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1921000000-962f62f2201c721e8295View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0629-9710000000-05994b472f188c352100View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-1014e75b24ff853934e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9143000000-7c532de871b5983afcd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9110000000-5faa45e484029ce5d481View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06150 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06150 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06150
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010661
KNApSAcK IDNot Available
Chemspider ID5132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfadimethoxine
METLIN IDNot Available
PubChem Compound5323
PDB IDNot Available
ChEBI ID32161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot 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 ]