Avlosulfon

Avlosulfon

Drug Information
Image	Dapsone.svg
Width	200
Caption
Synonyms	diaminodiphenyl sulfone (DDS)
Identifiers
CAS Number	80-08-0
ATC Prefix	D10
ATC Suffix	AX05
PubChem	2955
DrugBank	DB00250
ChemSpider ID
UNII	8W5C518302
KEGG	D00592
ChEBI	CHEBI:4325
ChEMBL	CHEMBL104
IUPAC Name	4-[(4-Aminobenzene)sulfonyl]aniline
Chemical Data
C
H
N
O
Molecular Weight

Avlosulfon, also known by its generic name dapsone, is a medication primarily used to treat leprosy and dermatitis herpetiformis. It is also used for other skin conditions and to prevent Pneumocystis pneumonia in people with HIV/AIDS. Avlosulfon belongs to a class of drugs known as sulfones.

Medical uses

Avlosulfon is effective in the treatment of several inflammatory and dermatological conditions. Its primary use is in the treatment of leprosy, where it is used as part of a multi-drug therapy, often including rifampicin and clofazimine. It is also used in the treatment of dermatitis herpetiformis, a skin condition associated with celiac disease, providing relief from the intense itching and rash.

Mechanism of action

The mechanism by which Avlosulfon works is not fully understood, but it is known to have both anti-inflammatory and antibacterial properties. It is thought to inhibit the synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for the active site of dihydropteroate synthase, an enzyme involved in bacterial folic acid synthesis.

Side effects

Common side effects of Avlosulfon include hemolysis (especially in individuals with glucose-6-phosphate dehydrogenase deficiency), methemoglobinemia, and gastrointestinal disturbances such as nausea and vomiting. Long-term use can lead to more serious conditions such as neuropathy and hemolytic anemia.

Pharmacokinetics

After oral administration, Avlosulfon is well absorbed from the gastrointestinal tract, with a bioavailability of 70–80%. It is extensively metabolized in the liver, primarily by cytochrome P450 2E1 (CYP2E1), and has a half-life of 20 to 30 hours. The drug is excreted mainly through urine and feces.

History

Avlosulfon was first synthesized in the 1940s and has been used in medical practice for over 70 years. It was initially developed as an antileprosy agent but was later found to be effective in treating other dermatological and autoimmune conditions.

Society and culture

Legal status of Avlosulfon varies by country, but it is generally available by prescription only. It is listed on the World Health Organization's List of Essential Medicines, indicating its importance in a basic health system.