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Compound Summary

General Compound Information

Dapsone

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Description

Dapsone is a sulfone that is diphenylsulfone in which the hydrogen atom at the 4 position of each of the phenyl groups is substituted by an amino group. It is active against a wide range of bacteria, but is mainly employed for its actions against Mycobacterium leprae, being used as part of multidrug regimens in the treatment of all forms of leprosy. It has a role as an antimalarial, a leprostatic drug, an antiinfective agent and an anti-inflammatory drug. It is a sulfone and a substituted aniline. It derives from a diphenyl sulfone.

Synonyms

dapsone; 80-08-0; 4,4'-Sulfonyldianiline; Diaphenylsulfone; 4,4'-Diaminodiphenyl sulfone;

4,4'-Diaminodiphenylsulfone;Dapson;4-Aminophenyl sulfone;Diaphenylsulfon;Novophone;Sulfona;DADPS;Bis(4-aminophenyl) sulfone;Avlosulfone;Diphenasone;Sulfadione;Sulphadione;Dapsonum;Disulone;Aczone;Udolac;p-Aminophenyl sulfone;Avlosulfon;Croysulfone;Dumitone;Diphone;Eporal;Diaphenylsulphon;Diaphenylsulphone;Metabolite C;Sumicure S;Bis(p-aminophenyl) sulfone;Sulphonyldianiline;p,p-Sulphonylbisbenzamine;Sulfona-MAE;Avlosulphone;Croysulphone;Dubronax;4,4'-Dapsone;Diaminodiphenyl sulfone;Tarimyl;p,p-Sulphonylbisbenzenamine;Sulfone ucb;Sulfonyldianiline;4,4'-Sulfonylbisaniline;p,p'-Diaminodiphenyl sulfone;4-(4-aminophenyl)sulfonylaniline;Dapsona;NSC-6091;Benzenamine, 4,4'-sulfonylbis-;Diaminodiphenylsulfone;Bis(4-aminophenyl)sulfone;Di(p-aminophenyl) sulfone;p,p-Sulphonyldianiline;4,4'-Sulfonylbisbenzamine;Di(4-aminophenyl) sulfone;p,p'-sulfonyldianiline;4,4'-Sulfonylbisbenzenamine;p,p-Sulfonylbisbenzamine;Diaminodifenilsulfona;DDS, pharmaceutical;Di(p-aminophenyl)sulphone;p,p-Sulfonylbisbenzenamine;Araldite HT 976;Bis(p-aminophenyl)sulphone;Di(4-aminophenyl)sulphone;Bis(4-aminophenyl)sulphone;p,p-Diaminodiphenyl sulphone;N,N'-Diphenyl sulfondiamide;1,1'-Sulfonylbis(4-aminobenzene);4,4'-Sulphonyldianiline;DDS;Servidapson;4,4'-Sulphonylbisbenzamine;4,4'-Sulphonylbisbenzenamine;4,4'-Diaminodiphenyl sulphone;WR 448;4,4-Diaminodifenylsulfon;Diamino-4,4'-diphenyl sulfone;Diamino-4,4'-diphenyl sulphone;NSC 6091D;NCI-C01718;1,1'-Sulfonylbis[4-aminobenzene];1,1'-Sulphonylbis(4-aminobenzene);Aniline, 4,4'-sulfonyldi-;HT 976;4,4'-diamino diphenyl sulphone;F 1358;4,4'-Sulfonyldianiline (Dapsone);1358F;4-[(4-aminobenzene)sulfonyl]aniline;4,4'-Sulfonylbisbenzeneamine;DTXSID4020371;4,4'-Sulfonyldianilin;Diaphenylsulfone (JAN);CHEMBL1043;MLS000069409;CHEBI:4325;NSC-6091D;Sulfanona-mae;J04BA02;NSC6091;Sulfon-mere;4,4'-DDS;Di(4-aminophenyl)sulfone;4-(4-amino-benzenesulfonyl)-phenylamine;NCGC00016322-08;SMR000059064;Hardener HT 976;DDS (pharmaceutical);Sulphon-mere;8W5C518302;Dapsonum [INN-Latin];Dapsona [INN-Spanish];DSS (VAN);DIAPHENYLSULFONE [JAN];DTXCID00371;4-Aminophenylsulfone;4 4-Diamino Diphenyl Sulfone 99.5%min Cas:80-08-8;DDS, diaphenylsulfone;4,4'-Diaminodiphenyl suphone;Atrisone;Diaminodifenilsulfona [Spanish];4,4-Diaminodifenylsulfon [Czech];CAS-80-08-0;HY 976;CCRIS 192;Dapsone (USP);Aczone (TN);1632119-29-9;HSDB 5073;SR-01000002976;NSC 6091;4-[(4-aminophenyl)sulfonyl]aniline;Sulfone, diphenyl, 4,4'-diamino-;EINECS 201-248-4;(4-sulfanilylphenyl)amine;MFCD00007887;AZT + Dapsone cominbation;BRN 0788055;AI3-08087;Diaphenyl sulfone;Dapsone [USAN:USP:INN:BAN];4-(4-aminobenzenesulfonyl)aniline;UNII-8W5C518302;Dapsone,(S);Prestwick_152;ALBB-005917;Dapsone-d8(major);Dapsone-[d4];IN-201;Dapsone-13C12;BIS SULFONE;4,4''-dapsone;4-[(4-Aminophenyl)sulfonyl]phenylamine;Dapsone-[15N2];Spectrum_000888;DAPSONE [VANDF];Aniline,4'-sulfonyldi-;DAPSONE [HSDB];DAPSONE [IARC];DAPSONE [USAN];DAPSONE [INN];DAPSONE [MI];DAPSONE [MART.];Opera_ID_1950;Prestwick0_000035;Prestwick1_000035;Prestwick2_000035;Prestwick3_000035;Spectrum2_001133;Spectrum3_000375;Spectrum4_000310;Spectrum5_000825;WLN: ZR DSWR DZ;4,4''-sulfonyldianiline;DAPSONE [USP-RS];DAPSONE [WHO-DD];DAPSONE [WHO-IP];4,4''-sulfonylbisaniline;EC 201-248-4;4,4'-Sulfonyldiphenylamine;Benzenamine,4'-sulfonylbis-;Oprea1_143052;SCHEMBL21428;BSPBio_000129;BSPBio_002129;CBDivE_013582;Dianiline, 4,4'-sulfonyl-;KBioGR_000900;KBioSS_001368;MLS001055349;MLS001076146;4,4''-Sulfonylbisbenzenamine;4,4'-Sulfonylbis[benzamine];4-Aminophenyl sulfone, 97%;BIDD:GT0770;DAPSONE [EP IMPURITY];DAPSONE [ORANGE BOOK];DivK1c_000573;p,p''-diaminodiphenyl sulfone;SPECTRUM1500222;SPBio_001025;SPBio_002050;DAPSONE [EP MONOGRAPH];4,4''-diaminodiphenyl sulfone;4,4'-diamino diphenyl sulfone;BPBio1_000143;ZINC6310;DAPSONE [USP MONOGRAPH];DAPSONUM [WHO-IP LATIN];GTPL10934;HMS501M15;KBio1_000573;KBio2_001368;KBio2_003936;KBio2_006504;KBio3_001349;4-(4-aminophenylsulfonyl)aniline;NINDS_000573;HMS1568G11;HMS1920C14;HMS2091K04;HMS2095G11;HMS2231G09;HMS3259C13;HMS3369B11;HMS3712G11;Pharmakon1600-01500222;Dapson 100 microg/mL in Methanol;ACT07431;AMY40781;HY-B0688;1,1''-sulfonylbis(4-aminobenzene);Tox21_110371;Tox21_201347;Tox21_300558;4-(4-aminophenylsulfonyl)benzenamine;BBL002412;BDBM50029764;CCG-40260;NSC756716;s4612;STK387118;AKOS000119322;Tox21_110371_1;DB00250;HT 9664;KS-1450;NC00488;NSC-756716;IDI1_000573;NCGC00016322-01;NCGC00016322-02;NCGC00016322-03;NCGC00016322-04;NCGC00016322-05;NCGC00016322-06;NCGC00016322-07;NCGC00016322-09;NCGC00016322-10;NCGC00016322-13;NCGC00023946-03;NCGC00023946-04;NCGC00023946-05;NCGC00023946-06;NCGC00254533-01;NCGC00258899-01;AC-10922;4-[(4-Aminophenyl)sulfonyl]phenylamine #;SBI-0051331.P003;DB-056406;AB00051962;D0089;Dapsone, VETRANAL(TM), analytical standard;FT-0624447;FT-0665473;4 inverted exclamation marka-Sulfonyldianiline;EN300-19042;C07666;D00592;AB00051962_19;A839828;Q422226;4 inverted exclamation marka-Diaminodiphenyl sulfone;4,4 inverted exclamation mark(R)-Sulfonyldianiline;Q-200435;SR-01000002976-2;SR-01000002976-4;BRD-K62363391-001-05-8;BRD-K62363391-001-15-7;SULFACETAMIDE SODIUM IMPURITY D [EP IMPURITY];Dapsone, British Pharmacopoeia (BP) Reference Standard;Dapsone, European Pharmacopoeia (EP) Reference Standard;F0266-3067;Z104472374;2-(PIPERAZIN-1-YL)-ACETICACIDN-(2-PHENYLETHYL)-AMIDE;4-(4-aminophenyl)sulfonylaniline;4,4'-Diaminodiphenyl sulfone;Dapsone, United States Pharmacopeia (USP) Reference Standard;Dapsone, Pharmaceutical Secondary Standard; Certified Reference Material;

FlavorDB ID

15 PUBCHEM ID

Molecular Weight

248.3 Molecular Formula

C12H12N2O2S

Openeye Can Smiles

C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N

IUPAC Inchikey

MQJKPEGWNLWLTK-UHFFFAOYSA-N

Network

Similarity

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
Overdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: 4,4'-Diaminodiphenyl sulphone

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Reference point information of this compound is not available!

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

OUTPUT ID	ASSESSMENT	QUALIFIER	VALUE	UNIT	POPULATION
343	critical study not identified		0		Consumers

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA AFC	2005	343	Negative

EFSA Outputs

Output ID	Title	DOI	Published
343	Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request related to a 9th list of substances for food contact materials	doi:10.2903/j.efsa.2005.248a	02Aug2005

Receptors

Receptor	REFERENCE	EC50 [µM]
TAS2R4	details	Activated
TAS2R10	details	Activated
TAS2R40	details	Activated

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative

Content

Compound Summary

Dapsone

Description

Synonyms

dapsone; 80-08-0; 4,4'-Sulfonyldianiline; Diaphenylsulfone; 4,4'-Diaminodiphenyl sulfone;

FlavorDB ID

15

PUBCHEM ID

2955

Molecular Weight

248.3

Molecular Formula

C12H12N2O2S

Openeye Can Smiles

C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N

IUPAC Inchikey

MQJKPEGWNLWLTK-UHFFFAOYSA-N

Network

Shown in network

Similarity

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Content

Compound Summary

Dapsone

Description

Synonyms

dapsone; 80-08-0; 4,4'-Sulfonyldianiline; Diaphenylsulfone; 4,4'-Diaminodiphenyl sulfone;

FlavorDB ID

15

PUBCHEM ID

2955

Molecular Weight

248.3

Molecular Formula

C12H12N2O2S

Openeye Can Smiles

C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N

IUPAC Inchikey

MQJKPEGWNLWLTK-UHFFFAOYSA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

OpenFoodTox: component 4,4'-Diaminodiphenyl sulphone

Reference Details

Reference Details

Reference Details

GC-MS Spectrum

GC-MS Spectrum