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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:14 UTC
Update Date2020-07-06 16:00:59 UTC
HMDB IDHMDB0013854
Secondary Accession Numbers
  • HMDB13854
Metabolite Identification
Common NameN4-Acetylsulfamethoxazole
DescriptionN4-Acetylsulfamethoxazole is a metabolite of the sulfonamide bacteriostatic antibiotic sulfamethoxazole. Sulfamethoxazole is metabolized via acetylation catalyzed by liver extramitochondrial N-acetyl transferases. Acetylsulfamethoxazole is excreted in urine. Acetylsulfamethoxazole and sulfamethoxazole can be used as a probe for the molecular percentage enrichment of liver extramitochondrial acetyl-CoA. N4-Acetylsulfamethoxazole can be used as a reference for measuring sulfamethoxazole impurities and waste determination (PMID: 15307787 ). It is one of the critical aspects of urine and stone analysis (PMID: 3811034 ) and its quantitative determination in body fluids could be performed by reversed-phase high-performance liquid chromatography, a rapid, precise and simple procedure (PMID: 6668314 ). It is also reported the renal excretion rate of the metabolite N4-acetylsulfamethoxazole is not dependent on the urinary pH (PMID: 670346 ). N4-Acetylsulfamethoxazole is only found in individuals who have consumed the drug sulfamethoxazole.
Structure
Data?1582753148
Synonyms
ValueSource
4'-((5-Methyl-3-isoxazolyl)sulfamoyl)acetanilideChEBI
AcetylsulfamethoxazoleChEBI
GantanolChEBI
N(4)-AcetylsulfisomezoleChEBI
N(4)-AcetylsulfulfamethoxazoleChEBI
SMX-AcetateChEBI
Sulfamethoxazole acetateChEBI
Sulfisomezole-N(4)-acetateChEBI
4'-((5-Methyl-3-isoxazolyl)sulphamoyl)acetanilideGenerator
AcetylsulphamethoxazoleGenerator
N(4)-AcetylsulphisomezoleGenerator
N(4)-AcetylsulphulfamethoxazoleGenerator
SMX-Acetic acidGenerator
Sulfamethoxazole acetic acidGenerator
Sulphamethoxazole acetateGenerator
Sulphamethoxazole acetic acidGenerator
Sulfisomezole-N(4)-acetic acidGenerator
Sulphisomezole-N(4)-acetateGenerator
Sulphisomezole-N(4)-acetic acidGenerator
N4-AcetylsulphamethoxazoleGenerator
N-{4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamideHMDB
N4-AcetylsulfisomezoleHMDB
N4-AcetylsulfulfamethoxazoleHMDB
Sulfisomezole-N4-acetateHMDB
N(4)-AcetylsulfamethoxazoleMeSH
N(4)-AcetylsulphamethoxazoleMeSH
N4-AcetylsulfamethoxazoleChEBI
N-AcetylsulphamethoxazoleGenerator
Chemical FormulaC12H13N3O4S
Average Molecular Weight295.314
Monoisotopic Molecular Weight295.062676609
IUPAC NameN-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid
Traditional NameN(sup 4)-acetylsulfisomezole
CAS Registry Number21312-10-7
SMILES
CC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1
InChI Identifier
InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)
InChI KeyGXPIUNZCALHVBA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Organosulfonic acid amide
  • Imidolactam
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Sulfonyl
  • Aminosulfonyl compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.86Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP1.13ALOGPS
logP1.58ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)5.68ChemAxon
pKa (Strongest Basic)0.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.79 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.41 m³·mol⁻¹ChemAxon
Polarizability28.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9360000000-1c2a094865717e2eaddeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9231000000-4a60dfa1fba628eae89eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0007-0490000000-52c719984f40afb2fe69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-885f5298dc9cac736ad2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-3845d94430e55b3672ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-0f28bd7306e116b23664Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-a931f6f79851f6517143Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0390000000-dba8d5adc6ad93ec8917Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-72a1ece66e1150c7e39eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0900000000-a95d8aa5899e8bda0fe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-34815ffdbcd4883ad2ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-1f10de1f050b43bd0fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000x-6900000000-6d4e7909426bd265f9caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0290000000-71d5ce544864c89f38cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-43bf3d487b565393cd9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0900000000-b0416b270d76be397989Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-25b614db8f59a5f5db39Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-2900000000-626694102c1eea16e5a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-7ce29f406bc6d908f6eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-5c819656360e2573a7d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-59a88d63e4fe9a3c607fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-dafe8db52ffd9aba90dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0090000000-dbdf81cedd451fbecf90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0940000000-7aeaac18bb12eed8efc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001j-0900000000-dfa2b385ed090efc32f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001j-0900000000-31016a4897f3a03c1868Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001j-0900000000-9c81e37f34949cbc56adSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58771
KEGG Compound IDC13061
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound80641
PDB IDNot Available
ChEBI ID31169
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gobel A, McArdell CS, Suter MJ, Giger W: Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem. 2004 Aug 15;76(16):4756-64. doi: 10.1021/ac0496603. [PubMed:15307787 ]
  2. Asper R, Schmucki O: Critical aspects of urine and stone analysis. Appearance of iatrogenic urinary calculi. Urol Int. 1986;41(5):334-42. doi: 10.1159/000281233. [PubMed:3811034 ]
  3. Weber A, Opheim KE, Siber GR, Ericson JF, Smith AL: High-performance liquid chromatographic quantitation of trimethoprim, sulfamethoxazole, and N4-acetylsulfamethoxazole in body fluids. J Chromatogr. 1983 Dec 9;278(2):337-45. doi: 10.1016/s0378-4347(00)84793-3. [PubMed:6668314 ]
  4. Vree TB, Hekster YA, Baars AM, Damsma JE, Kleijin EV: Determination of trimethoprim and sulfamethoxazole (co-trimoxazole) in body fluids of man by means of high-performance liquid chromatography. J Chromatogr. 1978 Jul 1;146(1):103-12. doi: 10.1016/s0378-4347(00)81294-3. [PubMed:670346 ]