Dapsone

Dapsone
Clinical data
Trade names	Aczone, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682128
License data	US DailyMed: Dapsone;
Routes of; administration	By mouth, topical
ATC code	D10AX05 (WHO) J04BA02 (WHO);
Legal status
Legal status	US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	70 to 80%
Protein binding	70 to 90%
Metabolism	Liver (mostly CYP2E1-mediated)
Elimination half-life	20 to 30 hours
Excretion	Kidney
Identifiers
	IUPAC name 4-[(4-aminobenzene)sulfonyl]aniline;
CAS Number	80-08-0 ;
PubChem CID	2955;
DrugBank	DB00250 ;
ChemSpider	2849 ;
UNII	8W5C518302;
KEGG	D00592 ;
ChEBI	CHEBI:4325 ;
ChEMBL	ChEMBL1043 ;
CompTox Dashboard (EPA)	DTXSID4020371 ;
ECHA InfoCard	100.001.136
Chemical and physical data
Formula	C12H12N2O2S
Molar mass	248.30 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	175 to 176 °C (347 to 349 °F)
	SMILES O=S(=O)(c1ccc(N)cc1)c2ccc(N)cc2;
	InChI 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 ; Key:MQJKPEGWNLWLTK-UHFFFAOYSA-N ;
	(verify)

Dapsone, also known as 4,4'-sulfonyldianiline (SDA) or diaminodiphenyl sulfone (DDS), is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy. It is a second-line medication for the treatment and prevention of pneumocystis pneumonia and for the prevention of toxoplasmosis in those who have poor immune function. Additionally, it has been used for acne, dermatitis herpetiformis, and various other skin conditions. Dapsone is available both topically and by mouth.

Severe side effects may include a decrease in blood cells, red blood cell breakdown especially in those with glucose-6-phosphate dehydrogenase deficiency (G-6-PD), or hypersensitivity. Common side effects include nausea and loss of appetite. Other side effects include liver inflammation, methemoglobinemia, and a number of types of skin rashes. While the safety of use during pregnancy is not entirely clear some physicians recommend that it be continued in those with leprosy. It is of the sulfone class.

Dapsone was first studied as an antibiotic in 1937. Its use for leprosy began in 1945. It is on the World Health Organization's List of Essential Medicines. The form, which is taken by mouth, is available as a generic drug and not very expensive.

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