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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:39 UTC
HMDB IDHMDB15150
Secondary Accession NumbersNone
Metabolite Identification
Common NameSulfamethoxazole
DescriptionSulfamethoxazole is only found in individuals that have used or taken this drug. It is a bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Structure
Thumb
Synonyms
ValueSource
3-(P-Aminophenylsulfonamido)-5-methylisoxazoleChEBI
3-Sulfanilamido-5-methylisoxazoleChEBI
4-amino-N-(5-Methyl-3-isoxazolyl)benzenesulfonamideChEBI
GantanolChEBI
SMXChEBI
3-(P-Aminophenylsulphonamido)-5-methylisoxazoleGenerator
SulphamethoxazoleGenerator
3-Sulphanilamido-5-methylisoxazoleGenerator
4-amino-N-(5-Methyl-3-isoxazolyl)benzenesulphonamideGenerator
3-(P-Aminobenzenesulfonamido)-5-methylisoxazoleHMDB
3-(Para-aminophenylsulphonamido)-5-methylisoxazoleHMDB
4-amino-N-(5-Methyl-1,2-oxazol-3-yl)benzenesulfonamideHMDB
4-amino-N-(5-Methyl-3-isoxazolyl)-benzenesulfonamideHMDB
5-Methyl-3-sulfanilamidoisoxazoleHMDB
5-Methyl-3-sulfanylamidoisoxazoleHMDB
5-Methyl-3-sulfonylamidoisoxazoleHMDB
5-Methyl-3-sulphanil-amidoisoxazoleHMDB
azo-GantanolHMDB
BactrimHMDB
MetoxalHMDB
N'-(5-methyl-3-isoxazole)sulfanilamideHMDB
N'-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
N'-(5-methyl-3-isoxazolyl)sulfanilamideHMDB
N'-(5-methylisoxazol-3-yl)sulphanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)-sulfanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)sulfanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)sulphanilamideHMDB
Ndimethyl1-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
N^1-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
RadonilHMDB
SimsinominHMDB
SinominHMDB
SulfamethalazoleHMDB
SulfamethoxazolHMDB
Sulfamethoxazole(usan)HMDB
SulfamethylisoxazoleHMDB
SulfisomezoleHMDB
Sulpha-methoxizoleHMDB
SulphamethoxazolHMDB
SulphamethylisoxazoleHMDB
SulphisomezoleHMDB
Chemical FormulaC10H11N3O3S
Average Molecular Weight253.278
Monoisotopic Molecular Weight253.052111923
IUPAC Name4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
Traditional Namesulfamethoxazole
CAS Registry Number723-46-6
SMILES
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
InChI Identifier
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChI KeyInChIKey=JLKIGFTWXXRPMT-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
  • Sulfonylaniline
  • Substituted aniline
  • Aniline
  • Imidolactam
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Oxazole
  • Isoxazole
  • Azole
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Anti-Infectives
  • Sulfonamides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point167 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.59e-01 g/LNot Available
LogP0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.46 mg/mLALOGPS
logP0.79ALOGPS
logP0.79ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.16ChemAxon
pKa (Strongest Basic)1.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.22 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.5 m3·mol-1ChemAxon
Polarizability24.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01015
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01015
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01015
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5138
KEGG Compound IDC07315
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamethoxazole
NuGOwiki LinkHMDB15150
Metagene LinkHMDB15150
METLIN IDNot Available
PubChem Compound5329
PDB ID08D
ChEBI ID9332
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hobday JD: The prophylactic treatment of recurrent urinary tract infection with sulphamethoxizole-trimethoprim. Aust Paediatr J. 1971 Dec;7(4):199-202. [5140758 ]
  2. Arora VK, Tumbanatham A, Kumar SV, Ratnakar C: Pneumocystis carinii pneumonia simulating as pulmonary tuberculosis in AIDS. Indian J Chest Dis Allied Sci. 1996 Oct-Dec;38(4):253-7. [9018980 ]