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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O3S
Molecular Weight 264.3
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAPSONE HYDROXYLAMINE

SMILES

NC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(NO)C=C2

InChI

InChIKey=IYDSJDWESCGRKW-UHFFFAOYSA-N
InChI=1S/C12H12N2O3S/c13-9-1-5-11(6-2-9)18(16,17)12-7-3-10(14-15)4-8-12/h1-8,14-15H,13H2

HIDE SMILES / InChI

Molecular Formula C12H12N2O3S
Molecular Weight 264.3
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Evaluation of the sulfones and streptomycin in experimental tuberculosis.
1949 Dec 14
Role of dapsone hydroxylamine in dapsone-induced hemolytic anemia.
1988 Jan
Dapsone-induced hemolytic anemia: effect of dapsone hydroxylamine on sulfhydryl status, membrane skeletal proteins and morphology of human and rat erythrocytes.
1995 Jul
Dapsone-induced hemolytic anemia: role of glucose-6-phosphate dehydrogenase in the hemolytic response of rat erythrocytes to N-hydroxydapsone.
1995 May
Oxidative stress, glucose-6-phosphate dehydrogenase and the red cell.
2001
Activation of cytochrome P450 2C9-mediated metabolism: mechanistic evidence in support of kinetic observations.
2003 Feb 1
The effect of clarithromycin, fluconazole, and rifabutin on dapsone hydroxylamine formation in individuals with human immunodeficiency virus infection (AACTG 283).
2004 Dec
Reduction of sulfamethoxazole and dapsone hydroxylamines by a microsomal enzyme system purified from pig liver and pig and human liver microsomes.
2005 May 27
Formation and uptake of arylhydroxylamine-haptenated proteins in human dendritic cells.
2007 Apr
Dapsone induces oxidative stress and impairs antioxidant defenses in rat liver.
2008 Aug 1
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:40:35 UTC 2023
Edited
by admin
on Thu Jul 06 16:40:35 UTC 2023
Record UNII
GS5815Z51W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAPSONE HYDROXYLAMINE
Common Name English
BENZENAMINE, 4-((4-AMINOPHENYL)SULFONYL)-N-HYDROXY-
Systematic Name English
NSC-742234
Code English
N-HYDROXY-4,4'-SULFONYLDI(ANILINE)
Systematic Name English
N-HYDROXYDAPSONE
Common Name English
4-(HYDROXYAMINO)-4'-AMINODIPHENYL SULFONE
Systematic Name English
Code System Code Type Description
NSC
742234
Created by admin on Thu Jul 06 16:40:35 UTC 2023 , Edited by admin on Thu Jul 06 16:40:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID30186361
Created by admin on Thu Jul 06 16:40:35 UTC 2023 , Edited by admin on Thu Jul 06 16:40:35 UTC 2023
PRIMARY
FDA UNII
GS5815Z51W
Created by admin on Thu Jul 06 16:40:35 UTC 2023 , Edited by admin on Thu Jul 06 16:40:35 UTC 2023
PRIMARY
PUBCHEM
65387
Created by admin on Thu Jul 06 16:40:35 UTC 2023 , Edited by admin on Thu Jul 06 16:40:35 UTC 2023
PRIMARY
CAS
32695-27-5
Created by admin on Thu Jul 06 16:40:35 UTC 2023 , Edited by admin on Thu Jul 06 16:40:35 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE TOXIC
Metabolite known for methaemoglobin formation in man.
METABOLITE -> PARENT
We have also shown recently that greater than 90% of dapsone hydroxylation in human liver microsomes is undertaken by cytochrome P4503A4
URINE