Dapsone

Dapsone
Clinical data


Trade names	Aczone
AHFS/Drugs.com	Monograph
MedlinePlus	a682128
Pregnancy category	AU: B2 US: C (Risk not ruled out)
Routes of administration	Oral, Topical
ATC code	D10AX05 (WHO) J04BA02 (WHO)
Legal status
Legal status	℞-only (U.S.), POM (UK)
Pharmacokinetic data
Bioavailability	70 to 80%
Protein binding	70 to 90%
Metabolism	Hepatic (mostly CYP2E1-mediated)
Biological half-life	20 to 30 hours
Excretion	Renal
Identifiers
IUPAC name 4-[(4-aminobenzene)sulfonyl]aniline
CAS Number	80-08-0^Y
PubChem (CID)	2955
DrugBank	DB00250^Y
ChemSpider	2849^Y
UNII	8W5C518302^Y
KEGG	D00592^Y
ChEBI	CHEBI:4325^Y
ChEMBL	CHEMBL1043^Y
ECHA InfoCard	100.001.136
Chemical and physical data
Formula	C₁₂H₁₂N₂O₂S
Molar mass	248.302 g/mol
3D model (Jmol)	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^Y Key:MQJKPEGWNLWLTK-UHFFFAOYSA-N^Y

Dapsone, also known as 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 and a number of types of skin rashes. While it is not entirely clear the safety of use during pregnancy 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 most effective and safe medicines needed in a health system. The oral form is available as a generic drug and not very expensive.

Dapsone is commonly used in combination with rifampicin and clofazimine for the treatment of leprosy. It is also used to both treat and prevent pneumocystis pneumonia (PCP). It is also used for toxoplasmosis in people unable to tolerate trimethoprim with sulfamethoxazole.

...
Wikipedia