Survey with prize
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
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:34 UTC
HMDB IDHMDB0014395
Secondary Accession Numbers
  • HMDB14395
Metabolite Identification
Common NameDapsone
DescriptionDapsone, also known as diaphenylsulfone or 4,4'-dapsone, 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. Its mechanism of action is probably similar to that of the sulfonamides which involves inhibition of folic acid synthesis in susceptible organisms. Dapsone is a drug which is used for the treatment and management of leprosy and dermatitis herpetiformis. Dapsone is a moderately basic compound (based on its pKa). Dapsone is a potentially toxic compound. A sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Overdosage might be expected to produce nasal congestion, syncope, or hallucinations.
Structure
Data?1582753174
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
AczoneKegg
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 dapsoneHMDB
SulfonaHMDB
4,4' Diaminophenyl sulfoneHMDB
4,4'-Diaminophenyl sulfoneHMDB
Dapson-fatolHMDB
DisuloneHMDB
Fatol brand OF dapsoneHMDB
Orsade brand OF dapsoneHMDB
Sulfone, 4,4'-diaminophenylHMDB
SulfonyldianilineHMDB
AvlosulfoneHMDB
Dapsoderm-XHMDB
DiaminodiphenylsulfoneHMDB
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
Description 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.19ALOGPS
logP1.27ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.99 m³·mol⁻¹ChemAxon
Polarizability25.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0564-9770000000-98d678eb70ae9cdbbfaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-5901100000-901603cf86087b4a4abbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0190000000-7de0f1aeb77cf9b122f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0290000000-f1e61c46f1720875a177Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0920000000-ed66532a51b7d047462aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-3900000000-a1f636a2e557bc9b69a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9800000000-3557ad8246dc0a0aa05cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-5910000000-0c8eb03605a271970f1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-0590000000-a23b099ad5d2d3cd716dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-1920000000-0260de715fec538fe8bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-5900000000-6ba41fa3598abafdb242Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-9600000000-d2fe4c5ba425499ba98cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-9400000000-e29e2bdac763fc5e250bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9200000000-71494cee2792628e6a0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-38433ad894a5e08f6ee0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-e4782e47ceb05d1ffbdaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-4ab9019e60b1718d1d29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0190000000-d7cf0928be57fafd7ea4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-1930000000-09cf0e392eeef139f2b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-8900000000-5da3a6d058cb14fc8300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-77f73a73b1a222285be3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-efb6858364a1d7c22428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9430000000-d9c6fe280d40d0bc8dd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-f3d8a4bdccbe1170ae6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-ab2b74cff1f89de7c9a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9020000000-d4698e6b7c05ce3e71e6Spectrum
MSMass Spectrum (Electron Ionization)splash10-052g-8930000000-c51783649020dadfb20fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00250 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00250 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00250
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2849
KEGG Compound IDC07666
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDapsone
METLIN IDNot Available
PubChem Compound2955
PDB IDNot Available
ChEBI ID4325
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]