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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:49:01 UTC
HMDB IDHMDB0014404
Secondary Accession Numbers
  • HMDB14404
Metabolite Identification
Common NameSulfanilamide
DescriptionSulfanilamide is only found in individuals that have used or taken this drug. It is a molecule containing the sulfonamide functional group attached to an aniline. [Wikipedia]Sulfanilamide is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. This enzyme normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid. The inhibited reaction is normally necessary in these organisms for the synthesis of folic acid. Without it, bacteria cannot replicate.
Structure
Thumb
Synonyms
ValueSource
4-Aminobenzene sulfonic acid amideChEBI
4-AzanylbenzenesulfonamideChEBI
P-AminobenzenesulfamideChEBI
P-AminobenzenesulfonamideChEBI
Para-aminobenzenesulfonamideChEBI
Prontosil albumChEBI
SAChEBI
StreptocideChEBI
SulfamineChEBI
SulphanilamideChEBI
4-Aminobenzene sulfonate amideGenerator
4-Aminobenzene sulphonate amideGenerator
4-Aminobenzene sulphonic acid amideGenerator
4-AzanylbenzenesulphonamideGenerator
P-AminobenzenesulphamideGenerator
P-AminobenzenesulphonamideGenerator
Para-aminobenzenesulphonamideGenerator
SulphamineGenerator
P-AminobenzenesulfonylamideHMDB
P-AminobenzensulfonamideHMDB
P-AminophenylsulfonamideHMDB
P-AnilinesulfonamideHMDB
P-SulfamidoanilineHMDB
P-SulfamoylanilineHMDB
PABSHMDB
Sulfanilimidic acidHMDB
SulfonylamideHMDB
SulphonamideHMDB
Sulfanilamide cadmium saltMeSH
Sulfanilamide hydrochlorideMeSH
Sulfanilamide strontium saltMeSH
Sulfanilamide zinc saltMeSH
Sulfanilamide monohydrateMeSH
Azol polvoMeSH
Sulfanilamide magnesium saltMeSH
Sulfanilamide silver saltMeSH
Sulfanilamide sodium saltMeSH
4-AminobenzenesulfonamideMeSH
Sulfanilamide barium saltMeSH
Sulfanilamide lithium saltMeSH
Chemical FormulaC6H8N2O2S
Average Molecular Weight172.205
Monoisotopic Molecular Weight172.0306482
IUPAC Name4-aminobenzene-1-sulfonamide
Traditional Namesulfanilamide
CAS Registry Number63-74-1
SMILES
NC1=CC=C(C=C1)S(N)(=O)=O
InChI Identifier
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
InChI KeyFDDDEECHVMSUSB-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
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 g/LNot Available
LogP-0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-0.16ALOGPS
logP-0.25ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.92 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0avl-9800000000-517ec40f53253fdb0135View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0avl-9800000000-517ec40f53253fdb0135View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05c6-9500000000-b4fc349159a78c29204bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-0900000000-50278150b601ad9e8f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-0900000000-43cb75637a921937a7a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-5900000000-50aaf376888d903aa161View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0h93-9400000000-cf00412f8d6022da5a4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02h9-9100000000-d798abed368c30f832c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-9000000000-5cd62daf8fa463f7b17cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-35e0f674b075951ffbd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-e034dc2633255b5189e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-9100000000-429f5368f3041a82ca5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-9790929fd4527de66731View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-57504c1880586c76aa3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-9ce799cd3421de1a0eaeView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00259 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00259 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00259
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5142
KEGG Compound IDC07458
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfanilamide
METLIN IDNot Available
PubChem Compound5333
PDB IDSAN
ChEBI ID45373
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. Epub 2006 Sep 7. [PubMed:16997145 ]

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
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 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
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 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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 ]