DAPSONE

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

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	MOL RATIO 1 MOL RATIO (average)

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

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 44	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Acne vulgaris 34	Curative	Approved 8,429	ACZONE
Dermatitis herpetiformis 9	Curative	Approved 8,429	DAPSONE
Leprosy 5	Curative	Approved 8,429	DAPSONE

C_max

Value	Dose	Co-administered	Analyte	Population
19.7 ng/mL	110 mg 2 times / day steady-state, topical		DAPSONE plasma	Homo sapiens
1375 ng/mL	100 mg single, oral		DAPSONE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
415 ng × h/mL	110 mg 2 times / day steady-state, topical	DAPSONE plasma	Homo sapiens
22783 ng × h/mL	100 mg single, oral	DAPSONE plasma	Homo sapiens
52641 ng × h/mL	100 mg single, oral	DAPSONE plasma	Homo sapiens
221.52 ng × h/mL	110 mg 2 times / day steady-state, topical	DAPSONE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
42 h	110 mg 2 times / day steady-state, topical		DAPSONE plasma	Homo sapiens
20.6 h	100 mg single, oral		DAPSONE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%	unknown, unknown		DAPSONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
300 mg 1 times / week multiple, oral Highest studied dose	unhealthy, 38	Disc. AE: Anemia, Rash...
200 mg 1 times / week multiple, oral MTD	unhealthy, 38	Disc. AE: Vomiting, Fever...
10 g single, oral Overdose	unhealthy, 45	Disc. AE: Cyanosis, Methaemoglobinaemia...

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AEs

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AE	Significance	Dose	Population
Anemia	11.1% Disc. AE	300 mg 1 times / week multiple, oral Highest studied dose	unhealthy, 38
Fever	11.1% Disc. AE	300 mg 1 times / week multiple, oral Highest studied dose	unhealthy, 38
Rash	11.1% Disc. AE	300 mg 1 times / week multiple, oral Highest studied dose	unhealthy, 38
Fever	14.3% Disc. AE	200 mg 1 times / week multiple, oral MTD	unhealthy, 38
Vomiting	14.3% Disc. AE	200 mg 1 times / week multiple, oral MTD	unhealthy, 38

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037 activator 22

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 693 CYP2E1 667

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1,819	activator 214	likely

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Drug as victim

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Target	Modality	Activity
CYP2C8 693	substrate 3,367	yes
CYP2C9 1,037	substrate 3,367	yes
CYP2E1 667	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes

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Sourcing

Sourcing

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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
eMolecules	17392619	https://www.emolecules.com/cgi-bin/more?vid=17392619
eMolecules	498059	https://www.emolecules.com/cgi-bin/more?vid=498059
MolPort	MolPort-001-780-172	https://www.molport.com/shop/molecule-link/MolPort-001-780-172

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PubMed

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Title	Date	PubMed
Dapsone-induced motor polyneuropathy. A complication of prolonged treatment of subcorneal pustular dermatosis.	1976 Aug	182085
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
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

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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.