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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 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. Dapsone is a drug which is used for the treatment and management of leprosy and dermatitis herpetiformis. Based on a literature review a significant number of articles have been published on Dapsone.
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 effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP0.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available151.709http://allccs.zhulab.cn/database/detail?ID=AllCCS00000800
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.12931661259
DarkChem[M-H]-158.97631661259
DeepCCS[M+H]+163.22530932474
DeepCCS[M-H]-160.86730932474
DeepCCS[M-2H]-193.82130932474
DeepCCS[M+Na]+169.31830932474
AllCCS[M+H]+157.332859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+160.832859911
AllCCS[M+Na]+161.832859911
AllCCS[M-H]-154.032859911
AllCCS[M+Na-2H]-154.032859911
AllCCS[M+HCOO]-154.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DapsoneNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C14492.4Standard polar33892256
DapsoneNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C12901.0Standard non polar33892256
DapsoneNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C12873.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dapsone,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C12961.1Semi standard non polar33892256
Dapsone,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C12654.9Standard non polar33892256
Dapsone,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C13591.3Standard polar33892256
Dapsone,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C13233.8Semi standard non polar33892256
Dapsone,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C12783.6Standard non polar33892256
Dapsone,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C13104.2Standard polar33892256
Dapsone,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2956.2Semi standard non polar33892256
Dapsone,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2706.0Standard non polar33892256
Dapsone,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C3376.8Standard polar33892256
Dapsone,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C13149.4Semi standard non polar33892256
Dapsone,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12813.2Standard non polar33892256
Dapsone,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12936.7Standard polar33892256
Dapsone,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C3080.4Semi standard non polar33892256
Dapsone,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2886.7Standard non polar33892256
Dapsone,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2743.8Standard polar33892256
Dapsone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C13217.7Semi standard non polar33892256
Dapsone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C12899.3Standard non polar33892256
Dapsone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C13600.8Standard polar33892256
Dapsone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C13718.3Semi standard non polar33892256
Dapsone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C13236.5Standard non polar33892256
Dapsone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C13216.9Standard polar33892256
Dapsone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C3481.4Semi standard non polar33892256
Dapsone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C3146.8Standard non polar33892256
Dapsone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C3383.3Standard polar33892256
Dapsone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13898.1Semi standard non polar33892256
Dapsone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13450.6Standard non polar33892256
Dapsone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13148.5Standard polar33892256
Dapsone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3996.1Semi standard non polar33892256
Dapsone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3734.5Standard non polar33892256
Dapsone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3042.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dapsone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0564-9770000000-98d678eb70ae9cdbbfaa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dapsone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052g-8930000000-c51783649020dadfb20f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-qTof , Positive-QTOFsplash10-0a4i-5901100000-901603cf86087b4a4abb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOFsplash10-0002-0190000000-7de0f1aeb77cf9b122f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOFsplash10-0002-0290000000-f1e61c46f1720875a1772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOFsplash10-0a4i-0920000000-ed66532a51b7d047462a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOFsplash10-0a4l-3900000000-a1f636a2e557bc9b69a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOFsplash10-052f-9800000000-3557ad8246dc0a0aa05c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QTOF , positive-QTOFsplash10-0a4i-5910000000-0c8eb03605a271970f1d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-052b-0590000000-a23b099ad5d2d3cd716d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-0a4i-1920000000-0260de715fec538fe8bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-0a4l-5900000000-6ba41fa3598abafdb2422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-052f-9600000000-d2fe4c5ba425499ba98c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-052f-9400000000-e29e2bdac763fc5e250b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-066u-9200000000-71494cee2792628e6a0c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-38433ad894a5e08f6ee02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-e4782e47ceb05d1ffbda2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-4ab9019e60b1718d1d292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOFsplash10-0002-0190000000-d7cf0928be57fafd7ea42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOFsplash10-0a4i-1930000000-09cf0e392eeef139f2b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOFsplash10-0a4l-8900000000-5da3a6d058cb14fc83002017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 10V, Positive-QTOFsplash10-0002-0090000000-77f73a73b1a222285be32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 20V, Positive-QTOFsplash10-0002-0090000000-efb6858364a1d7c224282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 40V, Positive-QTOFsplash10-004i-9430000000-d9c6fe280d40d0bc8dd62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 10V, Negative-QTOFsplash10-0002-0090000000-f3d8a4bdccbe1170ae6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 20V, Negative-QTOFsplash10-0002-0090000000-ab2b74cff1f89de7c9a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dapsone 40V, Negative-QTOFsplash10-0006-9020000000-d4698e6b7c05ce3e71e62016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
Good Scents IDrw1198951
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 ]