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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

PubMed

PubMed

TitleDatePubMed
Erythema nodosum leprosum in Nigeria.
1975 Nov
Dapsone induced motor polyneuropathy.
1992 Jun
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Management difficulties due to concurrent dermatitis herpetiformis and variegate porphyria.
2000 Sep
The IL-8 release from cultured human keratinocytes, mediated by antibodies to bullous pemphigoid autoantigen 180, is inhibited by dapsone.
2001 Apr
Antimicrobial activities of dihydrofolate reductase inhibitors, used singly or in combination with dapsone, against Mycobacterium ulcerans.
2001 Jan
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
[A case of relapsing polychondritis monitored by daily peak flow measurement].
2001 Jul
A trial of proguanil-dapsone in comparison with sulfadoxine-pyrimethamine for the clearance of Plasmodium falciparum infections in Tanzania.
2001 Jul-Aug
Eosinophilic pustular folliculitis (Ofuji's disease): indomethacin as a first choice of treatment.
2001 Mar
[Hypersensitivity syndrome and HHV-6].
2001 Nov
Immunohematotoxicity studies with combinations of dapsone and zidovudine.
2001 Nov
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
[Case of herpes gestationis in 5th pregnancy].
2002
[A 50-year history of new drugs in Japan: the developments of antileprosy drugs and their epidemiological aspects].
2002
[Bioavailability of isoniazid in healthy volunteers--fast and slow INH acetylators].
2002
Mutations in dhfr in Plasmodium falciparum infections selected by chlorproguanil-dapsone treatment.
2002 Dec 15
Vitamin E for dapsone-induced headache.
2002 Jan
Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells.
2002 Nov
Bioavailability factors of isoniazid in fast and slow acetylators, healthy volunteers.
2002 Nov-Dec
[Two cases of Hansen's disease].
2003 Aug
A second case of multidrug-resistant Mycobacterium leprae isolated from a Japanese patient with relapsed lepromatous leprosy.
2003 Sep
A near fatal case of the dapsone hypersensitivity syndrome in a patient with urticarial vasculitis.
2003 Sep
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.
2003 Sep
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
2004 Jan 1
Monitoring of ELISA for anti-BP180 antibodies: clinical and therapeutic analysis of steroid-treated patients with bullous pemphigoid.
2004 May
A convenient five-drug cocktail for the assessment of major drug metabolizing enzymes: a pilot study.
2004 Sep
Dapsone syndrome with acute renal failure during leprosy treatment: case report.
2005 Feb
[Dapsone-induced agranulocytosis. The role of xenobiotic-metabolizing enzymes demonstrated by a case report].
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Robust acoustic object detection.
2005 Oct
Acute methemoglobinemia following attempted suicide by Dapson.
2006 Apr
The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations.
2006 Jun 6
The sulfone syndrome secondary to dapsone prophylaxis in a patient undergoing unrelated hematopoietic stem cell transplantation.
2006 Sep
Neuroprotective effect of dapsone in patients with acute ischemic stroke: a pilot study.
2007 Apr
Consultative meeting to develop a strategy for treatment of cutaneous leishmaniasis. Institute Pasteur, Paris. 13-15 June, 2006.
2007 Apr 24
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.
2007 Dec
Dapsone-induced haemolytic anaemia, hepatitis and agranulocytosis in a leprosy patient with normal glucose-6-phosphate-dehydrogenase activity.
2008 Dec
Beneficial effects of word final stress in segmenting a new language: evidence from ERPs.
2008 Feb 18
A novel assay system for myeloperoxidase activity in whole saliva.
2008 May
The processing of English regular inflections: Phonological cues to morphological structure.
2008 Oct
Complete atrioventricular block associated with dapsone therapy: a rare complication of dapsone-induced hypersensitivity syndrome.
2009 Aug
Patents

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
SULFACETAMIDE SODIUM IMPURITY D [EP]
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
DAPSONE [IARC]
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 Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
NCI_THESAURUS C849
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
WHO-VATC QD10AX05
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
WHO-ATC J04BA02
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
WHO-VATC QJ04BA02
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
WHO-ATC D10AX05
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
FDA ORPHAN DRUG 85694
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
NDF-RT N0000175881
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
NDF-RT N0000008053
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
FDA ORPHAN DRUG 61291
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
EPA PESTICIDE CODE 690107
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
LIVERTOX 264
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
FDA ORPHAN DRUG 61191
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
Code System Code Type Description
HSDB
80-08-0
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
MESH
D003622
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
PUBCHEM
2955
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
EVMPD
SUB06909MIG
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL1043
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
CAS
80-08-0
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
LactMed
80-08-0
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
RXCUI
3108
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
201-248-4
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
MERCK INDEX
M4092
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY Merck Index
INN
1676
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DAPSONE
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
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 Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
DRUG BANK
DB00250
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
NCI_THESAURUS
C415
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY
EPA CompTox
80-08-0
Created by admin on Mon Oct 21 19:49:44 UTC 2019 , Edited by admin on Mon Oct 21 19:49:44 UTC 2019
PRIMARY