dapsone

Also known as 4,4'-Diaminodiphenylsulfone, DDS, 4,4'-Sulfonyldianilin, 4,4'-sulfonyldianiline, DADPS, P,P-Sulphonylbisbenzamine, Bis(P-aminophenyl) sulfone, P,P'-diaminodiphenyl sulfone

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 460773489
Drug.IUPAC_name: 4-[(4-aminobenzene)sulfonyl]aniline
Drug.image: Dapsone.svg
Drug.image_class: skin-invert-image
Drug.image2: Dapsone3d.png
Drug.image_class2: bg-transparent
Drug.tradename: Aczone, others
Drug.MedlinePlus: a682128
Drug.DailyMedID: Dapsone
Drug.pregnancy_US: C
Drug.routes_of_administration: By mouth, topical
Drug.legal_AU: S4
Drug.legal_US: Rx-only
Drug.legal_status: Rx-only
Drug.bioavailability: 70 to 80%
Drug.protein_bound: 70 to 90%
Drug.metabolism: Liver (mostly CYP2E1-mediated)

via Wikipedia infobox

Chemical data

Formula: C12H12N2O2S
Molecular weight: 248.3 g/mol
IUPAC name: 4-(4-aminophenyl)sulfonylaniline
SMILES: C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
InChIKey: MQJKPEGWNLWLTK-UHFFFAOYSA-N
XLogP: 1
Polar surface area: 94.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

7,492 papers

Dapsone Use in Dermatology.American journal of clinical dermatology · 2024
Dapsone.Dermatology online journal · 2002
Dapsone for acne: Still in use after half a century!Journal of cosmetic dermatology · 2021
Dapsone-associated fixed drug eruption.Expert review of clinical pharmacology · 2017
Dapsone-induced methemoglobinemia.The Annals of pharmacotherapy · 1998

via PubMed

Wikidata facts

Mass: 248.061949

Show 6 more facts

melting point: 177
chemical formula: C₁₂H₁₂N₂O₂S
World Health Organisation international non-proprietary name: dapsone
canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
defined daily dose: 50
Commons category: Dapsone

Sources (7)

via Wikidata · CC0

~12 min read

Article

20 sections

Contents

Medical uses
Infections
Autoimmune disease
Other
Contraindications and precautions
Adverse effects
Blood
Liver
Skin
Dapsone hypersensitivity syndrome
Other adverse effects
Mechanism of action
History
Discovery
Proposed use in antimalarial drugs
Dapsone gel
Other uses
See also
References
External links

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.