DAPSONE

First approved in 1955

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 Search

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

Molecular Formula	C12H12N2O2S
Molecular Weight	248.301
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://escholarship.org/uc/item/30m4b5kr
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24310318	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Acne vulgaris 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021794s013lbl.pdf	Curative	Approved 8360	ACZONE Approved Use Gel is indicated for the topical treatment of acne vulgaris. Launch Date -4.73385599E11
Dermatitis herpetiformis 9 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fc98c9b-b17a-f66f-055b-259207ad9504	Curative	Approved 8360	DAPSONE Approved Use Dermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance. Launch Date 2.99807998E11
Leprosy 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fc98c9b-b17a-f66f-055b-259207ad9504	Curative	Approved 8360	DAPSONE Approved Use Dermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance. Launch Date 2.99807998E11

C_max

Value	Dose	Co-administered	Analyte	Population
1375 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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

Value	Dose	Analyte	Population
221.52 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
20.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% REVIEW https://pubmed.ncbi.nlm.nih.gov/3530584	unknown, unknown		DAPSONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	Disc. AE: Anemia, Rash... AEs leading to discontinuation/dose reduction: Anemia (11.1%) Rash (11.1%) Fever (11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	Disc. AE: Vomiting, Fever... AEs leading to discontinuation/dose reduction: Vomiting (14.3%) Fever (14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582
10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216	unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216	Disc. AE: Cyanosis, Methaemoglobinaemia... AEs leading to discontinuation/dose reduction: Cyanosis (acute) Methaemoglobinaemia Haemolysis Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 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: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582	unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/7979291 Page: p.1582
Haemolysis	Disc. AE	10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216	unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216
Methaemoglobinaemia	Disc. AE	10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216	unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216
Cyanosis	acute Disc. AE	10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216	unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6660028 Page: p.216

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709	substrate 1010 activator 21

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 688 CYP2E1 648

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1803	activator 210 Sources: https://pubmed.ncbi.nlm.nih.gov/11408370/	likely

Drug as victim

Target	Modality	Activity
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19998329/	yes
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19998329/	yes
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19998329/	yes
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19998329/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4325	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4325
ChemicalBook	CB0152851	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0152851
MolPort	MolPort-001-780-172	https://www.molport.com/shop/molecule-link/MolPort-001-780-172
ZINC	ZINC000000006310	http://zinc15.docking.org/substances/ZINC000000006310
eMolecules	17392619	https://www.emolecules.com/cgi-bin/more?vid=17392619
eMolecules	498059	https://www.emolecules.com/cgi-bin/more?vid=498059

PubMed

Title	Date	PubMed
Evaluation of the sulfones and streptomycin in experimental tuberculosis.	1949 Dec 14	15398779
Dapsone-induced hemolytic anemia: effect of N-hydroxy dapsone on the sulfhydryl status and membrane proteins of rat erythrocytes.	1992 Dec	1471153
Dapsone suppresses integrin-mediated neutrophil adherence function.	1992 Feb	1732379
Dapsone induced motor polyneuropathy.	1992 Jun	1332194
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Dapsone hypersensitivity syndrome with coexisting acute hepatitis E.	2000 Apr-Jun	10812824
Molecular evidence of greater selective pressure for drug resistance exerted by the long-acting antifolate Pyrimethamine/Sulfadoxine compared with the shorter-acting chlorproguanil/dapsone on Kenyan Plasmodium falciparum.	2000 Jun	10837185
The IL-8 release from cultured human keratinocytes, mediated by antibodies to bullous pemphigoid autoantigen 180, is inhibited by dapsone.	2001 Apr	11359455
[Hypersensitivity syndrome and HHV-6].	2001 Nov	11712420
Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats.	2002 Apr	12030789
Vitamin E for dapsone-induced headache.	2002 Jan	11841391
Dapsone.	2002 Jun	12165212
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	12451431
Bioavailability factors of isoniazid in fast and slow acetylators, healthy volunteers.	2002 Nov-Dec	12669770
[Helicobacter pylori eradication based upon a drug sensitivity test effectively increased platelet count in a patient with refractory idiopathic thrombocytopenic purpura].	2003 Jul	12931570
N-acetyltransferase 2 acetylation polymorphism: prevalence of slow acetylators does not differ between atopic dermatitis patients and healthy subjects.	2003 Nov-Dec	14528063
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	12920490
A case of refractory bullous pemphigoid with plasmapheresis-associated thrombopenia: efficacy of pulsed intravenous cyclophosphamide therapy.	2004 Aug	15492438
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	14695838
Neuroprotective effect of dapsone in an occlusive model of focal ischemia in rats.	2004 Mar 5	14759500
Differential activation of CYP2C9 variants by dapsone.	2004 May 15	15130760
A convenient five-drug cocktail for the assessment of major drug metabolizing enzymes: a pilot study.	2004 Sep	15327588
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Childhood bullous pemphigoid successfully treated with diaminodiphenyl sulfone.	2005 Oct	16361732
Renal hypersensitivity vasculitis associated with dapsone.	2005 Oct	16183407
The contribution of prosody to the perception of foreign accent.	2006	17293645
[Disulone and hepatosiderosis].	2006 Aug-Sep	17053738
The Dapsone hypersensitivity syndrome revisited: a potentially fatal multisystem disorder with prominent hepatopulmonary manifestations.	2006 Jun 6	16756657
The sulfone syndrome secondary to dapsone prophylaxis in a patient undergoing unrelated hematopoietic stem cell transplantation.	2006 Sep	16639690
High risk of severe anaemia after chlorproguanil-dapsone+artesunate antimalarial treatment in patients with G6PD (A-) deficiency.	2008	19112496
[A case of relapsing polychondritis monitored by repeated measurements of flow-volume curve].	2008 Mar	18409570
A novel assay system for myeloperoxidase activity in whole saliva.	2008 May	18237554
Dapsone-induced hemolytic anemia in lung allograft recipients.	2008 Nov	18971091
A possible inhibitory action of diaminodiphenyl sulfone on tumour necrosis factor-alpha production from activated mononuclear cells on cutaneous lupus erythematosus.	2008 Nov	18713254
Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats.	2008 Nov 15	18615706
Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation.	2009 Mar	18563518

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: Other

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.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 21:35:22 UTC 2023` Edited by `admin` on `Thu Jul 06 21:35:22 UTC 2023`
Record UNII	8W5C518302
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAPSONE

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

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