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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O2S
Molecular Weight 248.301
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAPSONE

SMILES

NC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(N)C=C2

InChI

InChIKey=MQJKPEGWNLWLTK-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Dapsone was synthesized in 1908 by Fromm and Wittmann. The drug was approved by FDA for the treatment of such conditions as acne vulgaris, leprosy and dermatitis herpetiformis, also the drug is used off-label for many skin diseases. Although the exact mechanism of dapsone action is unknown, it is speculated that it acts as both anti-inflammatory and antimicrobial agent. It was demonstrated that dapsone suppresses ROS generation, inhibits neutrophil myeloperoxidase and eosinophil peroxidase and also inhibits bacterial dihydropteroate synthase.

CNS Activity

Originator

Approval Year

1955
90
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
6467
Acne Vulgaris
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Bacterial dihydropteroate synthase
Approved
7678
DAPSONE
Primary
Bacterial dihydropteroate synthase
Approved
7678
DAPSONE
Primary
Bacterial dihydropteroate synthase
Approved
7678
ACZONE
Approved (off-label)
23
Approved (off-label)
23
PubMed

PubMed

TitleDatePubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.
2005 Nov
Dapsone induces oxidative stress and impairs antioxidant defenses in rat liver.
2008 Aug 1
[A case of relapsing polychondritis monitored by repeated measurements of flow-volume curve].
2008 Mar
A possible inhibitory action of diaminodiphenyl sulfone on tumour necrosis factor-alpha production from activated mononuclear cells on cutaneous lupus erythematosus.
2008 Nov
Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats.
2008 Nov 15
The processing of English regular inflections: Phonological cues to morphological structure.
2008 Oct
Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation.
2009 Mar
Patents

Patents

JP2002511777A
359
JP2002520419A
49
JP2003002952A
1
JP2006057108A
1
JP2007532680A
4
JP2008169291A
1
JP2009527631A
2
JP2010053278A
1
JP2010538103A
1
JP2011506398A
18
JP4728220B2
15
JP4787165B2
88
JPH00446923A
1
JPH01204935A
1
JPH02124950A
2
JPH02127420A
1
JPH02172914A
1
JPH06184512A
1
JPH0680947A
1
JPH072672A
2
JPH09260851A
1
JPH10178034A
1
JPH10178251A
1
JPH11343391A
1
JPS59207918A
1
JPS5924719A
1
JPS60258223A
1
JPS61231021A
1
JPS62106927A
3
JPS62153349A
1
JPS63305918A
1

Sample Use Guides

In Vivo Use Guide
Apply 5% gel to the acne affected areas twice a day (Aczone gel). In dermatitis herpetiformis, the starting oral dose is 50 mg and in leprosy, the dose is 100 mg/day (Dapsone oral formulation).
Route of Administration: Topical; Oral
In Vitro Use Guide
With Staphylococcus aureus (both methicillin-susceptible S. aureus-MSSA and methicillinresistant S. aureus-MRSA), dapsone MIC50, MIC90 were 128 ug/mL and 256 ug/mL, respectively. For Staphylococcus epidermidis overall, dapsone MIC50, MIC90 were 128 ug/mL and 256 ug/mL, respectively. Overall results with Enterococcus faecalis, dapsone MIC50, MIC90 were 256 ug/mL and 512 ug/mL, respectively. With Streptococcus agalactiae, dapsone MIC50, MIC90 were reported overall to be 32 ug/mL and 256 ug/mL, respectively. For Streptococcus pyogenes, dapsone MIC50, MIC90 were 32 ug/mL and 512 ug/mL, respectively.
Name Type Language
DAPSONE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
DAPSONE [VANDF]
Common Name English
ACZONE
Brand Name English
DAPSONE [WHO-IP]
Common Name English
NSC-6091
Code English
DAPSONE [INN]
Common Name English
DAPSONE [USP]
Common Name English
4,4'-SULFONYLDIANILINE
Systematic Name English
DAPSONE [HSDB]
Common Name English
SULPHADIONE
Common Name English
DAPSONE [MART.]
Common Name English
NOVOPHONE
Common Name English
DAPSONUM [WHO-IP LATIN]
Common Name English
DAPSONE [EP]
Common Name English
J04BA02
Code English
DIAPHENYLSULFONE [JAN]
Common Name English
DIAPHENYLSULFONE
JAN  
Common Name English
BENZENAMINE, 4,4'-SULFONYLBIS-
Systematic Name English
DAPSONE [ORANGE BOOK]
Common Name English
DAPSONE [WHO-DD]
Common Name English
DAPSONE [MI]
Common Name English
DAPSONE [USP-RS]
Common Name English
NSC-6091D
Code English
DAPSONE [USAN]
Common Name English
SERVIDAPSON
Common Name English
Classification Tree Code System Code
NDF-RT N0000008053
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
WHO-VATC QD10AX05
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
WHO-ATC J04BA02
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
WHO-VATC QJ04BA02
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
WHO-ATC D10AX05
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
NDF-RT N0000175881
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
NDF-RT N0000008053
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
EPA PESTICIDE CODE 690107
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
LIVERTOX 264
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
Code System Code Type Description
HSDB
80-08-0
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
MESH
D003622
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
PUBCHEM
2955
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB06909MIG
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
ChEMBL
CHEMBL1043
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
CAS
80-08-0
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
LactMed
80-08-0
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
RXCUI
3108
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY RxNorm
ECHA (EC/EINECS)
201-248-4
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
MERCK INDEX
M4092
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY Merck Index
INN
1676
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DAPSONE
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY Description: A white or creamy white, crystalline powder; odourless. Solubility: Soluble in 7000 parts of water and in 30 parts of ethanol (~750 g/l) TS; soluble in acetone R.Category: Antileprotic. Storage: Dapsone should be kept in a tightly closed container, protected from light. Additional information: Even in the absence of light, Dapsone is gradually degraded on exposure to a humid atmosphere, thedecomposition being faster at higher temperatures.
WIKIPEDIA
DAPSONE
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
DRUG BANK
DB00250
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
NCI_THESAURUS
C415
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
EPA CompTox
80-08-0
Created by admin on Tue Mar 06 11:21:07 UTC 2018 , Edited by admin on Tue Mar 06 11:21:07 UTC 2018
PRIMARY
ACTIVE MOIETY
Structure of DAPSONE
METABOLITE (PARENT)
Structure of MONOACETYLDAPSONE
METABOLITE (PARENT)
Structure of AZOXYDAPSONE
METABOLITE TOXIC (PARENT)
Structure of DAPSONE HYDROXYLAMINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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