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Record Information
Version4.0
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-09-27 08:28:02 UTC
HMDB IDHMDB0015688
Secondary Accession Numbers
  • HMDB15688
Metabolite Identification
Common NameSulfamoxole
DescriptionSulfamoxole is only found in individuals that have used or taken this drug. It is a sulfonamide antibacterial. 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.
Structure
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • 2,4,5-trisubstituted 1,3-oxazole
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Organosulfonic acid amide
  • Azole
  • Oxazole
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
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, Positivesplash10-0903-9520000000-b17afcbf8fbe531fe5f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-3900000000-23eed4bc89bcf24079bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-0590000000-b63b59b327f5e5fee30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2920000000-e352f9ce158638c8d63aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ftf-9110000000-06f8a9a3d0a07b30754fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-4d3645049982bea395a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2930000000-178776a8f92cbb18ce74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000000-aa4062cd0b19cdf35d94View 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 DB08798 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08798 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08798
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]