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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015688
Secondary Accession Numbers
  • HMDB15688
Metabolite Identification
Common NameSulfamoxole
DescriptionSulfamoxole, also known as oxasulfa or sulphamoxolum, 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. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. Sulfamoxole is a drug which is used for the treatment of bacterial infection. Sulfamoxole is a moderately basic compound (based on its pKa). Sulfamoxole 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. However, many strains of an individual species may be resistant.
Structure
Data?1582753323
Synonyms
ValueSource
2-(p-Aminobenzenesulfonamido)-4,5-dimethyloxazoleChEBI
2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazolChEBI
4,5-Dimethyl-2-sulfanilamidooxazoleChEBI
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamideChEBI
N1-(4,5-Dimethyl-2-oxazolyl)sulfanilamideChEBI
OxasulfaChEBI
p-Aminobenzenesulfonyl-2-amino-4,5-dimethyloxazoleChEBI
SulfadimethyloxazoleChEBI
SulfamoxolChEBI
SulfamoxolumChEBI
SulphamoxoleChEBI
2-(p-Aminobenzenesulphonamido)-4,5-dimethyloxazoleGenerator
2-(p-Aminobenzolsulphonamido)-4,5-dimethyloxazolGenerator
4,5-Dimethyl-2-sulphanilamidooxazoleGenerator
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulphonamideGenerator
N1-(4,5-Dimethyl-2-oxazolyl)sulphanilamideGenerator
OxasulphaGenerator
p-Aminobenzenesulphonyl-2-amino-4,5-dimethyloxazoleGenerator
SulphadimethyloxazoleGenerator
SulphamoxolGenerator
SulphamoxolumGenerator
SulfonoHMDB
Chemical FormulaC11H13N3O3S
Average Molecular Weight267.304
Monoisotopic Molecular Weight267.067761987
IUPAC Name4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
Traditional Namesulfamoxole
CAS Registry Number729-99-7
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 KeyCYFLXLSBHQBMFT-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
  • 2,4,5-trisubstituted 1,3-oxazole
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Azole
  • Oxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.51 m³·mol⁻¹ChemAxon
Polarizability27.44 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]+162.42931661259
DarkChem[M-H]-164.54431661259
DeepCCS[M+H]+160.98530932474
DeepCCS[M-H]-158.62730932474
DeepCCS[M-2H]-192.10230932474
DeepCCS[M+Na]+167.28130932474
AllCCS[M+H]+160.632859911
AllCCS[M+H-H2O]+156.932859911
AllCCS[M+NH4]+164.032859911
AllCCS[M+Na]+165.032859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-158.432859911
AllCCS[M+HCOO]-158.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfamoxoleCC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O14095.1Standard polar33892256
SulfamoxoleCC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O12486.7Standard non polar33892256
SulfamoxoleCC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O12522.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfamoxole,1TMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12827.1Semi standard non polar33892256
Sulfamoxole,1TMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12516.8Standard non polar33892256
Sulfamoxole,1TMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13536.6Standard polar33892256
Sulfamoxole,1TMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12564.4Semi standard non polar33892256
Sulfamoxole,1TMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12437.0Standard non polar33892256
Sulfamoxole,1TMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13740.0Standard polar33892256
Sulfamoxole,2TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12610.5Semi standard non polar33892256
Sulfamoxole,2TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12572.8Standard non polar33892256
Sulfamoxole,2TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13208.9Standard polar33892256
Sulfamoxole,2TMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12685.1Semi standard non polar33892256
Sulfamoxole,2TMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12613.4Standard non polar33892256
Sulfamoxole,2TMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13285.5Standard polar33892256
Sulfamoxole,3TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12540.3Semi standard non polar33892256
Sulfamoxole,3TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12708.0Standard non polar33892256
Sulfamoxole,3TMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13049.4Standard polar33892256
Sulfamoxole,1TBDMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13060.3Semi standard non polar33892256
Sulfamoxole,1TBDMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N12732.9Standard non polar33892256
Sulfamoxole,1TBDMS,isomer #1CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13545.6Standard polar33892256
Sulfamoxole,1TBDMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12813.6Semi standard non polar33892256
Sulfamoxole,1TBDMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12659.2Standard non polar33892256
Sulfamoxole,1TBDMS,isomer #2CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13704.8Standard polar33892256
Sulfamoxole,2TBDMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13095.5Semi standard non polar33892256
Sulfamoxole,2TBDMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13036.9Standard non polar33892256
Sulfamoxole,2TBDMS,isomer #1CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13295.8Standard polar33892256
Sulfamoxole,2TBDMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13175.9Semi standard non polar33892256
Sulfamoxole,2TBDMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13039.0Standard non polar33892256
Sulfamoxole,2TBDMS,isomer #2CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13321.3Standard polar33892256
Sulfamoxole,3TBDMS,isomer #1CC1=C(C)OC(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)=N13243.4Semi standard non polar33892256
Sulfamoxole,3TBDMS,isomer #1CC1=C(C)OC(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)=N13408.5Standard non polar33892256
Sulfamoxole,3TBDMS,isomer #1CC1=C(C)OC(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)=N13222.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamoxole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0903-9520000000-b17afcbf8fbe531fe5f32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamoxole 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 - Sulfamoxole LC-ESI-QTOF , positive-QTOFsplash10-0a4i-3900000000-23eed4bc89bcf24079bd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 15V, Positive-QTOFsplash10-066r-0960000000-5324e421d0898ec1099e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 75V, Positive-QTOFsplash10-07bf-9500000000-9e755c5d161870e20cc12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOFsplash10-0bt9-4900000000-f0d6577fe251f478a2b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 25V, Positive-QTOFsplash10-05mo-9600000000-656e8ab90054a33c8a962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 80V, Positive-QTOFsplash10-066u-9400000000-4d435cd7a788a59f537f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 45V, Positive-QTOFsplash10-014i-9100000000-8c8c9b244225730711352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOFsplash10-05mo-9300000000-6e87579d1c4dcc3385d32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 45V, Positive-QTOFsplash10-066u-9400000000-328720644b3d39690ea82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 50V, Positive-QTOFsplash10-014i-9000000000-70248a5e493d759c89082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 75V, Positive-QTOFsplash10-014i-9000000000-2d46e7d146924e2cc1ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 60V, Positive-QTOFsplash10-014i-9100000000-b69806557c6ee27e2cf52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 35V, Positive-QTOFsplash10-014l-9200000000-8def04b9696db26636182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOFsplash10-0a4i-0900000000-b95f9545732c76bf65ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 15V, Positive-QTOFsplash10-0btc-6900000000-747f05ef6971ea73b0132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOFsplash10-0bt9-4900000000-78c0ee8433765de7a0212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 20V, Positive-QTOFsplash10-0btc-9800000000-21eddbd29f724651aeea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 25V, Positive-QTOFsplash10-0a4i-0910000000-66e1d1317255c54345a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamoxole 35V, Positive-QTOFsplash10-0a4i-1900000000-c35120697abf544edf882021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 10V, Positive-QTOFsplash10-0gi0-0590000000-b63b59b327f5e5fee30d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 20V, Positive-QTOFsplash10-00di-2920000000-e352f9ce158638c8d63a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 40V, Positive-QTOFsplash10-0ftf-9110000000-06f8a9a3d0a07b30754f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 10V, Negative-QTOFsplash10-014i-0190000000-4d3645049982bea395a32016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 20V, Negative-QTOFsplash10-00di-2930000000-178776a8f92cbb18ce742016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamoxole 40V, Negative-QTOFsplash10-002f-9400000000-aa4062cd0b19cdf35d942016-08-04Wishart 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 DB08798 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08798 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08798
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12361
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamoxole
METLIN IDNot Available
PubChem Compound12894
PDB IDNot Available
ChEBI ID55548
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]