Dapsone

Dapsone
Clinical data
Trade namesAczone, others
AHFS/Drugs.comMonograph
MedlinePlusa682128
License data
Routes of
administration		By mouth, topical
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability70 to 80%
Protein binding70 to 90%
MetabolismLiver (mostly CYP2E1-mediated)
Elimination half-life20 to 30 hours
ExcretionKidney
Identifiers
  • 4-[(4-aminobenzene)sulfonyl]aniline
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.136 Edit this at Wikidata
Chemical and physical data
FormulaC12H12N2O2S
Molar mass248.30 g·mol−1
3D model (JSmol)
Melting point175 to 176 °C (347 to 349 °F)
  • O=S(=O)(c1ccc(N)cc1)c2ccc(N)cc2
  • 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 checkY
  • Key:MQJKPEGWNLWLTK-UHFFFAOYSA-N checkY
  (verify)

Dapsone, also known as 4,4'-sulfonyldianiline (SDA) or diaminodiphenyl sulfone (DDS),[2] is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy.[3] 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.[3] Additionally, it has been used for acne, dermatitis herpetiformis, and various other skin conditions.[4] Dapsone is available both topically and by mouth.[5]

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.[3] Common side effects include nausea and loss of appetite.[5] Other side effects include liver inflammation, methemoglobinemia,[6] and a number of types of skin rashes.[3] While the safety of use during pregnancy is not entirely clear some physicians recommend that it be continued in those with leprosy.[3] It is of the sulfone class.[3]

Dapsone was first studied as an antibiotic in 1937.[4] Its use for leprosy began in 1945.[4] It is on the World Health Organization's List of Essential Medicines.[7] The form, which is taken by mouth, is available as a generic drug and not very expensive.[3][8]

  1. ^ "Dapsone Use During Pregnancy". Drugs.com. 11 November 2019. Retrieved 17 May 2020.
  2. ^ Lemke TL (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 1142. ISBN 9780781768795. Archived from the original on 2016-03-04.
  3. ^ a b c d e f g "Dapsone (Systemic) Monograph for Professionals". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-12. Retrieved January 12, 2015.
  4. ^ a b c Zhu YI, Stiller MJ (September 2001). "Dapsone and sulfones in dermatology: overview and update". Journal of the American Academy of Dermatology. 45 (3): 420–434. doi:10.1067/mjd.2001.114733. PMID 11511841. S2CID 39874987.
  5. ^ a b Gallant JE (2008). Johns Hopkins HIV Guide 2012. Jones & Bartlett Publishers. p. 193. ISBN 9781449619794. Archived from the original on 2016-03-04.
  6. ^ Ash-Bernal R, Wise R, Wright SM (September 2004). "Acquired methemoglobinemia: a retrospective series of 138 cases at 2 teaching hospitals". Medicine. 83 (5): 265–273. doi:10.1097/01.md.0000141096.00377.3f. PMID 15342970. S2CID 40957843.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ Greenwood D (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. Oxford University Press. p. 197. ISBN 9780199534845. Archived from the original on 2016-03-04.