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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015621
Secondary Accession Numbers
  • HMDB15621
Metabolite Identification
Common NameSulfadimethoxine
DescriptionSulfadimethoxine, also known as abcid or agribon, 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. It is widely available in Russia as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies. Sulfadimethoxine is a drug which is used for use in the treatment of infections. Sulfadimethoxine is a moderately basic compound (based on its pKa). Sulfadimethoxine (trade name Di-Methox) is a sulfonamide antibacterial. Long-acting sulfonamide, antibacterial agent. Sulfadimethoxine is used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. Sulfadimethoxine has been shown to be effective against streptococci, klebsiella, proteus, shigella, staphylococci, escherichia, and salmonella.
Structure
Data?1582753317
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
DeposulHMDB
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
Description 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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-McLean172.3830932474
[M+H]+McLean170.1630932474
[M+H]+Not Available167.748http://allccs.zhulab.cn/database/detail?ID=AllCCS00000719
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.08431661259
DarkChem[M-H]-171.66731661259
DeepCCS[M+H]+174.1830932474
DeepCCS[M-H]-171.82230932474
DeepCCS[M-2H]-204.70930932474
DeepCCS[M+Na]+180.27330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfadimethoxineCOC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C14644.4Standard polar33892256
SulfadimethoxineCOC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C12874.4Standard non polar33892256
SulfadimethoxineCOC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C12810.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfadimethoxine,1TMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N13179.5Semi standard non polar33892256
Sulfadimethoxine,1TMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N12814.8Standard non polar33892256
Sulfadimethoxine,1TMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N14404.5Standard polar33892256
Sulfadimethoxine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N12861.2Semi standard non polar33892256
Sulfadimethoxine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N12738.2Standard non polar33892256
Sulfadimethoxine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N14531.9Standard polar33892256
Sulfadimethoxine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N12912.8Semi standard non polar33892256
Sulfadimethoxine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N12855.0Standard non polar33892256
Sulfadimethoxine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC(OC)=N13934.1Standard polar33892256
Sulfadimethoxine,2TMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N12891.6Semi standard non polar33892256
Sulfadimethoxine,2TMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N12870.0Standard non polar33892256
Sulfadimethoxine,2TMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N14084.6Standard polar33892256
Sulfadimethoxine,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N12794.8Semi standard non polar33892256
Sulfadimethoxine,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N12945.1Standard non polar33892256
Sulfadimethoxine,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC(OC)=N13693.8Standard polar33892256
Sulfadimethoxine,1TBDMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13394.3Semi standard non polar33892256
Sulfadimethoxine,1TBDMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13034.4Standard non polar33892256
Sulfadimethoxine,1TBDMS,isomer #1COC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N14364.8Standard polar33892256
Sulfadimethoxine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N13130.9Semi standard non polar33892256
Sulfadimethoxine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N12965.2Standard non polar33892256
Sulfadimethoxine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N14490.3Standard polar33892256
Sulfadimethoxine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13389.7Semi standard non polar33892256
Sulfadimethoxine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13302.0Standard non polar33892256
Sulfadimethoxine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13942.8Standard polar33892256
Sulfadimethoxine,2TBDMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13406.4Semi standard non polar33892256
Sulfadimethoxine,2TBDMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13296.4Standard non polar33892256
Sulfadimethoxine,2TBDMS,isomer #2COC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N14016.8Standard polar33892256
Sulfadimethoxine,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13488.7Semi standard non polar33892256
Sulfadimethoxine,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13594.7Standard non polar33892256
Sulfadimethoxine,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC(OC)=N13789.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfadimethoxine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4950000000-007497762ea1c35c4e342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfadimethoxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-qTof , Positive-QTOFsplash10-0a4i-3910000000-0ac9853510aee42140062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-000t-0960000000-4c56988c713477efd1052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0009000000-f2128f2fce62999cb7162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0009000000-ccda245feefab7d2bd862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-2429000000-29cebf2b6eb7f0d6fa3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-014i-8910000000-8accee4b36ee278d892f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-014i-9700000000-4424c4504af2babbb3be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-014i-9600000000-83e5ad4bc8bfce2e07132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0009000000-88d4fd97a1710d90ea0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0009000000-d5196629814cc9a54aa82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-0a4i-2429000000-d8e5bcd5f851f3c928872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-01b9-6900000000-64279bf9c022308e0a222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-01b9-8900000000-3ace2e3886f14e2ea9202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-014i-9400000000-e2fed07103b2f17ab4cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-ITFT , negative-QTOFsplash10-000t-0960000000-e0d34039fdec2c7162852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-QFT , negative-QTOFsplash10-0a4i-0009000000-6a816a27b2d84825241f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-QTOF , positive-QTOFsplash10-0bt9-0905000000-78aa6da956c32ba362412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0910000000-7b5873eb9276bcb413be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadimethoxine LC-ESI-QTOF , positive-QTOFsplash10-0k96-0910000000-24de656de5a8714caacb2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 10V, Positive-QTOFsplash10-03di-0329000000-144fa34c18dc427b24202016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 20V, Positive-QTOFsplash10-0a4i-1921000000-962f62f2201c721e82952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 40V, Positive-QTOFsplash10-0629-9710000000-05994b472f188c3521002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 10V, Negative-QTOFsplash10-0a4i-0029000000-1014e75b24ff853934e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 20V, Negative-QTOFsplash10-0a4i-9143000000-7c532de871b5983afcd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadimethoxine 40V, Negative-QTOFsplash10-0a4i-9110000000-5faa45e484029ce5d4812016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06150 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]