You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-03-02 21:33:11 UTC
HMDB IDHMDB14395
Secondary Accession NumbersNone
Metabolite Identification
Common NameDapsone
DescriptionA sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Its mechanism of action is probably similar to that of the sulfonamides which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with pyrimethamine in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
Structure
Thumb
Synonyms
ValueSource
1,1'-Sulfonylbis(4-aminobenzene)ChEBI
4,4'-DapsoneChEBI
4,4'-Diaminodiphenyl sulfoneChEBI
4,4'-SulfonylbisanilineChEBI
4,4'-SulfonylbisbenzenamineChEBI
4-(4-amino-Benzenesulfonyl)-phenylamineChEBI
4-(4-Aminophenylsulfonyl)anilineChEBI
4-(4-Aminophenylsulfonyl)benzenamineChEBI
4-Aminophenyl sulfoneChEBI
Bis(4-aminophenyl)sulfoneChEBI
Bis(P-aminophenyl) sulfoneChEBI
DADPSChEBI
DapsonaChEBI
DapsonumChEBI
DDSChEBI
DIAPHENYLsulfoneChEBI
P,P'-diaminodiphenyl sulfoneChEBI
P,P-SulphonylbisbenzamineChEBI
P,P-SulphonylbisbenzenamineChEBI
P-Aminophenyl sulfoneChEBI
1,1'-Sulphonylbis(4-aminobenzene)Generator
4,4'-Diaminodiphenyl sulphoneGenerator
4,4'-SulphonylbisanilineGenerator
4,4'-SulphonylbisbenzenamineGenerator
4-(4-amino-Benzenesulphonyl)-phenylamineGenerator
4-(4-Aminophenylsulphonyl)anilineGenerator
4-(4-Aminophenylsulphonyl)benzenamineGenerator
4-Aminophenyl sulphoneGenerator
Bis(4-aminophenyl)sulphoneGenerator
Bis(P-aminophenyl) sulphoneGenerator
DIAPHENYLsulphoneGenerator
P,P'-diaminodiphenyl sulphoneGenerator
P,P-SulfonylbisbenzamineGenerator
P,P-SulfonylbisbenzenamineGenerator
P-Aminophenyl sulphoneGenerator
1,1'-Sulfonylbis[4-aminobenzene]HMDB
4,4'-DiaminodiphenylsulfoneHMDB
4,4'-SulfonylbisbenzeneamineHMDB
4,4'-SulfonyldianilinHMDB
4,4'-SulfonyldianilineHMDB
DDS, PharmaceuticalHMDB
Mex-america brand OF dapsoneMeSH
SulfonaMeSH
4,4' Diaminophenyl sulfoneMeSH
4,4'-Diaminophenyl sulfoneMeSH
Dapson-fatolMeSH
DisuloneMeSH
Fatol brand OF dapsoneMeSH
Orsade brand OF dapsoneMeSH
Sulfone, 4,4'-diaminophenylMeSH
SulfonyldianilineMeSH
AvlosulfoneMeSH
Dapsoderm-XMeSH
DiaminodiphenylsulfoneMeSH
Chemical FormulaC12H12N2O2S
Average Molecular Weight248.301
Monoisotopic Molecular Weight248.061948328
IUPAC Name4-(4-aminobenzenesulfonyl)aniline
Traditional Namedapsone
CAS Registry Number80-08-0
SMILES
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChI KeyMQJKPEGWNLWLTK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonyl compounds
Direct ParentBenzenesulfonyl compounds
Alternative Parents
Substituents
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Sulfonyl
  • Sulfone
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Anti-Infectives
  • Anti-inflammatory Agents
  • Antimalarials
  • Antimycobacterials
  • Folic Acid Antagonists
  • Leprostatic Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.84e-01 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 mg/mLALOGPS
logP1.19ALOGPS
logP1.27ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.99 m3·mol-1ChemAxon
Polarizability25.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0190000000-7de0f1aeb77cf9b122f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0290000000-f1e61c46f1720875a177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0920000000-ed66532a51b7d047462aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-3900000000-a1f636a2e557bc9b69a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9800000000-3557ad8246dc0a0aa05cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-5910000000-0c8eb03605a271970f1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-0590000000-a23b099ad5d2d3cd716dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-1920000000-0260de715fec538fe8bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-5900000000-6ba41fa3598abafdb242View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-9600000000-d2fe4c5ba425499ba98cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-9400000000-e29e2bdac763fc5e250bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9200000000-71494cee2792628e6a0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-38433ad894a5e08f6ee0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-e4782e47ceb05d1ffbdaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-4ab9019e60b1718d1d29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0190000000-d7cf0928be57fafd7ea4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-1930000000-09cf0e392eeef139f2b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-8900000000-5da3a6d058cb14fc8300View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052f-9500000000-caa724a9dddce38f915bView in MoNA
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
MSMass Spectrum (Electron Ionization)splash10-052g-8930000000-c51783649020dadfb20fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 DB00250
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00250
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00250
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2849
KEGG Compound IDC07666
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDapsone
NuGOwiki LinkHMDB14395
Metagene LinkHMDB14395
METLIN IDNot Available
PubChem Compound2955
PDB IDNot Available
ChEBI ID4325
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Malfara WR, Pereira CP, Santos AC, Queiroz RH: Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats. Pharmacol Res. 2002 Apr;45(4):269-73. [PubMed:12030789 ]
  2. FLOCH H, GELARD AM: [Study of 4,4'-bis(ethylamino)-diphenylsulfone and of N-succinyl-4,4'diaminodiphenylsulfone administered intramuscularly in depot form]. Publ Inst Pasteur Guyane Fr Inini. 1954 Oct;15(343):1-7. [PubMed:14377653 ]