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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O2S
Molecular Weight 248.3024
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAPSONE

SMILES

c1cc(ccc1N)S(=O)(=O)c2ccc(cc2)N

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
Curator's Comment:: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021794s000_MicroR.pdf

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ACZONE

Approved Use

Gel is indicated for the topical treatment of acne vulgaris.

Launch Date

-473385600000
Curative
DAPSONE

Approved Use

Dermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance.

Launch Date

299808000000
Curative
DAPSONE

Approved Use

Dermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance.

Launch Date

299808000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1375 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DAPSONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
19.7 ng/mL
110 mg 2 times / day steady-state, topical
dose: 110 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
DAPSONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
221.52 ng × h/mL
110 mg 2 times / day steady-state, topical
dose: 110 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
DAPSONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
22783 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DAPSONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
415 ng × h/mL
110 mg 2 times / day steady-state, topical
dose: 110 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
DAPSONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
52641 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DAPSONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.6 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DAPSONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
42 h
110 mg 2 times / day steady-state, topical
dose: 110 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
DAPSONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown, unknown
DAPSONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / week multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / week
Route: oral
Route: multiple
Dose: 300 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Disc. AE: Anemia, Rash...
AEs leading to
discontinuation/dose reduction:
Anemia (11.1%)
Rash (11.1%)
Fever (11.1%)
Sources:
200 mg 1 times / week multiple, oral
MTD
Dose: 200 mg, 1 times / week
Route: oral
Route: multiple
Dose: 200 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Disc. AE: Vomiting, Fever...
AEs leading to
discontinuation/dose reduction:
Vomiting (14.3%)
Fever (14.3%)
Sources:
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M
Sources:
Disc. AE: Cyanosis, Methaemoglobinaemia...
AEs leading to
discontinuation/dose reduction:
Cyanosis (acute)
Methaemoglobinaemia
Haemolysis
Sources:
AEs

AEs

AESignificanceDosePopulation
Anemia 11.1%
Disc. AE
300 mg 1 times / week multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / week
Route: oral
Route: multiple
Dose: 300 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Fever 11.1%
Disc. AE
300 mg 1 times / week multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / week
Route: oral
Route: multiple
Dose: 300 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Rash 11.1%
Disc. AE
300 mg 1 times / week multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / week
Route: oral
Route: multiple
Dose: 300 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Fever 14.3%
Disc. AE
200 mg 1 times / week multiple, oral
MTD
Dose: 200 mg, 1 times / week
Route: oral
Route: multiple
Dose: 200 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Vomiting 14.3%
Disc. AE
200 mg 1 times / week multiple, oral
MTD
Dose: 200 mg, 1 times / week
Route: oral
Route: multiple
Dose: 200 mg, 1 times / week
Sources:
unhealthy, 38
Health Status: unhealthy
Age Group: 38
Sex: M+F
Sources:
Haemolysis Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M
Sources:
Methaemoglobinaemia Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M
Sources:
Cyanosis acute
Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
Drug as victim
PubMed

PubMed

TitleDatePubMed
Evaluation of the sulfones and streptomycin in experimental tuberculosis.
1949 Dec 14
Dapsone suppresses integrin-mediated neutrophil adherence function.
1992 Feb
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 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
A trial of proguanil-dapsone in comparison with sulfadoxine-pyrimethamine for the clearance of Plasmodium falciparum infections in Tanzania.
2001 Jul-Aug
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
[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
Dapsone-induced cholestasis and impairment of bile salt output in the rat.
2002 Apr 15
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002 Jun
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
[Dapsone-induced sensory peripheral neuropathy].
2003 Apr
Dapsone induced cholangitis as a part of dapsone syndrome: a case report.
2003 Aug 11
Unfolding of phonetic information over time: a database of Dutch diphone perception.
2003 Jan
[Helicobacter pylori eradication based upon a drug sensitivity test effectively increased platelet count in a patient with refractory idiopathic thrombocytopenic purpura].
2003 Jul
Synthesis and evaluation of analogues of Congo red as potential compounds against transmissible spongiform encephalopathies.
2003 Jun
[Treatment of relapsing polychondritis].
2003 Mar
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
A case of refractory bullous pemphigoid with plasmapheresis-associated thrombopenia: efficacy of pulsed intravenous cyclophosphamide therapy.
2004 Aug
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
Simultaneous determination of beta-blocking agents and diuretics in doping analysis by liquid chromatography/mass spectrometry with scan-to-scan polarity switching.
2005
Dapsone impairs the bile salt-independent fraction of bile flow in rats: Possible involvement of its N-hydroxylated metabolite.
2005 Jul 1
Aplastic anaemia associated with multidrug therapy (dapsone, rifampicin and clofazimine) in a patient with lepromatous leprosy.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Dapsone suppresses human neutrophil superoxide production and elastase release in a calcium-dependent manner.
2005 May
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.
2005 Nov
Complications related to dapsone use for Pneumocystis jirovecii pneumonia prophylaxis in solid organ transplant recipients.
2005 Nov
Childhood bullous pemphigoid successfully treated with diaminodiphenyl sulfone.
2005 Oct
Robust acoustic object detection.
2005 Oct
A case of drug-induced hypersensitivity syndrome with multiple organ involvement treated with plasma exchange.
2005 Oct
Renal hypersensitivity vasculitis associated with dapsone.
2005 Oct
The contribution of prosody to the perception of foreign accent.
2006
Acute methemoglobinemia following attempted suicide by Dapson.
2006 Apr
Anterior ischaemic optic neuropathy associated with Dapsone.
2006 Aug
[Disulone and hepatosiderosis].
2006 Aug-Sep
Guillain-Barré syndrome-like presentation in borderline leprosy with type-2 reaction.
2006 Feb 28
Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole.
2006 Jan
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
[Long-term follow-up of ofloxacin-combined therapy for leprosy patients].
2007 Sep
High risk of severe anaemia after chlorproguanil-dapsone+artesunate antimalarial treatment in patients with G6PD (A-) deficiency.
2008
Dapsone induces oxidative stress and impairs antioxidant defenses in rat liver.
2008 Aug 1
Complete atrioventricular block associated with dapsone therapy: a rare complication of dapsone-induced hypersensitivity syndrome.
2009 Aug
Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation.
2009 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fc98c9b-b17a-f66f-055b-259207ad9504
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: Other
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/27354888
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
SULFACETAMIDE SODIUM IMPURITY D [EP]
Common Name English
4,4'-SULFONYLDIANILINE
Systematic Name English
DAPSONE [USP MONOGRAPH]
Common Name English
DAPSONE [HSDB]
Common Name English
DAPSONE [EP MONOGRAPH]
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 Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
NCI_THESAURUS C849
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
WHO-VATC QD10AX05
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
WHO-ATC J04BA02
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
WHO-VATC QJ04BA02
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
WHO-ATC D10AX05
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
FDA ORPHAN DRUG 85694
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
NDF-RT N0000175881
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
NDF-RT N0000008053
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
FDA ORPHAN DRUG 61291
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
EPA PESTICIDE CODE 690107
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
LIVERTOX 264
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
FDA ORPHAN DRUG 61191
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
Code System Code Type Description
HSDB
5073
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
MESH
D003622
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PRIMARY
PUBCHEM
2955
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PRIMARY
EVMPD
SUB06909MIG
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL1043
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
FDA UNII
8W5C518302
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
CAS
80-08-0
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
RXCUI
3108
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
782
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PRIMARY
ECHA (EC/EINECS)
201-248-4
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
MERCK INDEX
M4092
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1164008
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY USP-RS
INN
1676
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DAPSONE
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
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 Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
LACTMED
Dapsone
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
DRUG BANK
DB00250
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
NCI_THESAURUS
C415
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY
EPA CompTox
80-08-0
Created by admin on Fri Jun 25 20:55:45 UTC 2021 , Edited by admin on Fri Jun 25 20:55:45 UTC 2021
PRIMARY