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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-27 08:27:32 UTC
HMDB IDHMDB0014408
Secondary Accession Numbers
  • HMDB14408
Metabolite Identification
Common NameSulfisoxazole
DescriptionSulfisoxazole is only found in individuals that have used or taken this drug. It is a short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem]Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Structure
Thumb
Synonyms
ValueSource
3,4-Dimethyl-5-sulfanilamidoisoxazoleChEBI
3,4-Dimethyl-5-sulfonamidoisoxazoleChEBI
3,4-Dimethyl-5-sulphanilamidoisoxazoleChEBI
3,4-Dimethyl-5-sulphonamidoisoxazoleChEBI
3,4-Dimethylisoxazole-5-sulfanilamideChEBI
3,4-Dimethylisoxazole-5-sulphanilamideChEBI
4-amino-N-(3,4-Dimethyl-5-isoxazolyl)benzenesulfonamideChEBI
4-amino-N-(3,4-Dimethyl-5-isoxazolyl)benzenesulphonamideChEBI
5-(4-Aminophenylsulfonamido)-3,4-dimethylisoxazoleChEBI
5-(P-Aminobenzenesulfonamido)-3,4-dimethylisoxazoleChEBI
5-(P-Aminobenzenesulphonamido)-3,4-dimethylisoxazoleChEBI
5-Sulfanilamido-3,4-dimethylisoxazoleChEBI
5-Sulphanilamido-3,4-dimethyl-isoxazoleChEBI
N'-(3,4)dimethylisoxazol-5-yl-sulphanilamideChEBI
N(1)-(3,4-Dimethyl-5-isoxazolyl)sulfanilamideChEBI
N(1)-(3,4-Dimethyl-5-isoxazolyl)sulphanilamideChEBI
SulfadimethylisoxazoleChEBI
SulfafurazolChEBI
SulfafurazoleChEBI
SulfafurazolumChEBI
SulfaisoxazoleChEBI
SulfasoxazoleChEBI
SulfisonazoleChEBI
SulfisoxasoleChEBI
SulfisoxazolChEBI
SulfofurazoleChEBI
SulphadimethylisoxazoleChEBI
SulphafurazolChEBI
SulphafurazoleChEBI
SulphaisoxazoleChEBI
SulphisoxazolChEBI
SulphofurazoleChEBI
SulphisoxazoleGenerator
5-(4-Aminophenylsulphonamido)-3,4-dimethylisoxazoleGenerator
5-Sulphanilamido-3,4-dimethylisoxazoleGenerator
5-Sulfanilamido-3,4-dimethyl-isoxazoleGenerator
N'-(3,4)dimethylisoxazol-5-yl-sulfanilamideGenerator
SulphafurazolumGenerator
SulphasoxazoleGenerator
SulphisonazoleGenerator
SulphisoxasoleGenerator
Sulfisoxazole dialamineHMDB
Sulfisoxazole diolamineHMDB
Ammonium salt sulfisoxazoleMeSH
Diolamine, sulfisoxazoleMeSH
Roche brand OF sulfisoxazoleMeSH
SulfasoxizoleMeSH
Sulfisoxazole roche brandMeSH
Sulfisoxazole, monosodium saltMeSH
TL-AzoleMeSH
V-SulMeSH
Pediatric, gantrisinMeSH
Sulfisoxazole, ammonium saltMeSH
Sulfisoxazole, monolithium saltMeSH
TL AzoleMeSH
V SulMeSH
Gantrisin pediatricMeSH
Monolithium salt sulfisoxazoleMeSH
Sulfisoxazole, monosodium, monomesylate saltMeSH
Vangard brand OF sulfisoxazoleMeSH
FNA brand OF sulfisoxazoleMeSH
GantrisinMeSH
Monosodium salt sulfisoxazoleMeSH
NeoxazoiMeSH
Roche brand OF sulfisoxazole acetateMeSH
Roche brand OF sulfisoxazole diolamineMeSH
SulfadimethyloxazoleMeSH
Sulfafurazol fnaMeSH
Sulfisoxazole, triammonium saltMeSH
Triammonium salt sulfisoxazoleMeSH
Zenith brand OF sulfisoxazoleMeSH
Chemical FormulaC11H13N3O3S
Average Molecular Weight267.304
Monoisotopic Molecular Weight267.067761987
IUPAC Name4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
Traditional Nameganda
CAS Registry Number127-69-5
SMILES
CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C
InChI Identifier
InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
InChI KeyNHUHCSRWZMLRLA-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
  • Organosulfonic acid amide
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP1.14ALOGPS
logP0.73ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)5.8ChemAxon
pKa (Strongest Basic)2.17ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.92 m³·mol⁻¹ChemAxon
Polarizability26.93 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, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-5911100000-18e92b64e6fb25ed4e6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-3900000000-23eed4bc89bcf24079bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-1930000000-47a2d9042541d8f86f85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2930000000-9fc0d3e8e143637637e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-5911100000-18e92b64e6fb25ed4e6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0190000000-67fdd03c85b2a068b40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-2390000000-541f0c03f60a901170c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyi-9010000000-ed61e7aa315127ee534dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-3fea2cb8533f6dac809aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9360000000-9a2a000e0d0fc02729a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-4c399debcac1dfd41d87View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00263 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00263 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00263
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5151
KEGG Compound IDC07318
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfisoxazole
METLIN IDNot Available
PubChem Compound5344
PDB IDNot Available
ChEBI ID102484
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 ]