DAPSONE

First approved in 1955

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 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

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 34	Inhibitor 7197	Dermatitis Herpetiformis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatitis Herpetiformis 10	Primary	Bacterial dihydropteroate synthase	Approved 7777	DAPSONE
Leprosy 5	Primary	Bacterial dihydropteroate synthase	Approved 7777	DAPSONE
Acne Vulgaris 68	Primary	Bacterial dihydropteroate synthase	Approved 7777	ACZONE
Idiopathic thrombocytopenic purpura 1			Approved (off-label) 7
[Pneumocystis jiroveci pneumonia, Bullous systemic lupus erythematosus, Aphthous ulcers] 1			Approved (off-label) 7

PubMed

Title	Date	PubMed
Dapsone-induced peripheral neuropathy.	1976 Dec	188385
[Polyneuropathy in Duhring dermatitis herpetiformis].	1991 Aug	1944718
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.	2001 Jan	11124226
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.	2007 Dec	19305740
High risk of severe anaemia after chlorproguanil-dapsone+artesunate antimalarial treatment in patients with G6PD (A-) deficiency.	2008	19112496
Dapsone-induced haemolytic anaemia, hepatitis and agranulocytosis in a leprosy patient with normal glucose-6-phosphate-dehydrogenase activity.	2008 Dec	19274991
Dapsone-induced hemolytic anemia in lung allograft recipients.	2008 Nov	18971091
Complex phase separation in poly(acrylonitrile-butadiene-styrene)-modified epoxy/4,4'-diaminodiphenyl sulfone blends: generation of new micro- and nanosubstructures.	2009 Apr 23	19331324
Complete atrioventricular block associated with dapsone therapy: a rare complication of dapsone-induced hypersensitivity syndrome.	2009 Aug	19583683
Representation of time-varying stimuli by a network exhibiting oscillations on a faster time scale.	2009 May	19412531
Establishment of knockdown of superoxide dismutase 2 and expression of CYP3A4 cell system to evaluate drug-induced cytotoxicity.	2009 Sep	19501153

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

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

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