U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O2S
Molecular Weight 248.301
Optical Activity NONE
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
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ACZONE

Approved Use

Gel is indicated for the topical treatment of acne vulgaris.

Launch Date

-4.73385599E11
Curative
DAPSONE

Approved Use

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

Launch Date

2.99807998E11
Curative
DAPSONE

Approved Use

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

Launch Date

2.99807998E11
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: Page: p.1582
unhealthy, 38
n = 9
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 9
Sources: Page: p.1582
Disc. AE: Anemia, Rash...
AEs leading to
discontinuation/dose reduction:
Anemia (11.1%)
Rash (11.1%)
Fever (11.1%)
Sources: Page: p.1582
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: Page: p.1582
unhealthy, 38
n = 7
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 7
Sources: Page: p.1582
Disc. AE: Vomiting, Fever...
AEs leading to
discontinuation/dose reduction:
Vomiting (14.3%)
Fever (14.3%)
Sources: Page: p.1582
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.216
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Dermatitis herpatiformis
Age Group: 45
Sex: M
Population Size: 1
Sources: Page: p.216
Disc. AE: Cyanosis, Methaemoglobinaemia...
AEs leading to
discontinuation/dose reduction:
Cyanosis (acute)
Methaemoglobinaemia
Haemolysis
Sources: Page: p.216
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: Page: p.1582
unhealthy, 38
n = 9
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 9
Sources: Page: p.1582
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: Page: p.1582
unhealthy, 38
n = 9
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 9
Sources: Page: p.1582
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: Page: p.1582
unhealthy, 38
n = 9
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 9
Sources: Page: p.1582
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: Page: p.1582
unhealthy, 38
n = 7
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 7
Sources: Page: p.1582
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: Page: p.1582
unhealthy, 38
n = 7
Health Status: unhealthy
Condition: Pneumocystis pneumonia
Age Group: 38
Sex: M+F
Population Size: 7
Sources: Page: p.1582
Haemolysis Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.216
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Dermatitis herpatiformis
Age Group: 45
Sex: M
Population Size: 1
Sources: Page: p.216
Methaemoglobinaemia Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.216
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Dermatitis herpatiformis
Age Group: 45
Sex: M
Population Size: 1
Sources: Page: p.216
Cyanosis acute
Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.216
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Dermatitis herpatiformis
Age Group: 45
Sex: M
Population Size: 1
Sources: Page: p.216
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
Drug as victim
PubMed

PubMed

TitleDatePubMed
[Granulomatous hepatitis caused by dapsone].
1992
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
[Dapsona syndrome].
2002 Jul
Dapsone.
2002 Jun
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
Synthesis and evaluation of analogues of Congo red as potential compounds against transmissible spongiform encephalopathies.
2003 Jun
[Treatment of relapsing polychondritis].
2003 Mar
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
A case of drug-induced hypersensitivity syndrome with multiple organ involvement treated with plasma exchange.
2005 Oct
Acute methemoglobinemia following attempted suicide by Dapson.
2006 Apr
[Disulone and hepatosiderosis].
2006 Aug-Sep
Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole.
2006 Jan
[Refractory cutaneous necrotizing vasculitis. Successful sulfone therapy].
2006 Jan
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
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 [IARC]
Common Name English
J04BA02
Code English
DIAPHENYLSULFONE [JAN]
Common Name English
DIAPHENYLSULFONE
JAN  
Common Name English
DAPSONE [EP IMPURITY]
Common Name English
BENZENAMINE, 4,4'-SULFONYLBIS-
Systematic Name English
DAPSONE [ORANGE BOOK]
Common Name English
DAPSONE [MI]
Common Name English
DAPSONE [USP-RS]
Common Name English
NSC-6091D
Code English
SULFACETAMIDE SODIUM IMPURITY D [EP IMPURITY]
Common Name English
DAPSONE [USAN]
Common Name English
Dapsone [WHO-DD]
Common Name English
SERVIDAPSON
Common Name English
Classification Tree Code System Code
NDF-RT N0000008053
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
NCI_THESAURUS C849
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
WHO-VATC QD10AX05
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
WHO-ATC J04BA02
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
WHO-VATC QJ04BA02
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
WHO-ATC D10AX05
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
FDA ORPHAN DRUG 85694
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
NDF-RT N0000175881
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
NDF-RT N0000008053
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
FDA ORPHAN DRUG 61291
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
EPA PESTICIDE CODE 690107
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
LIVERTOX NBK548936
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
FDA ORPHAN DRUG 61191
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
Code System Code Type Description
DAILYMED
8W5C518302
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
HSDB
5073
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
MESH
D003622
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
PUBCHEM
2955
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
EVMPD
SUB06909MIG
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL1043
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
FDA UNII
8W5C518302
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
CAS
80-08-0
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
RXCUI
3108
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
782
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-248-4
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
MERCK INDEX
M4092
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY Merck Index
SMS_ID
100000083461
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
RS_ITEM_NUM
1164008
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
CHEBI
4325
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
INN
1676
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DAPSONE
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
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 Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
LACTMED
Dapsone
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
DRUG BANK
DB00250
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
NSC
6091
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
NCI_THESAURUS
C415
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID4020371
Created by admin on Thu Jul 06 21:35:23 UTC 2023 , Edited by admin on Thu Jul 06 21:35:23 UTC 2023
PRIMARY