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),^[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]

^ "Dapsone Use During Pregnancy". Drugs.com. 11 November 2019. Retrieved 17 May 2020.
^ Lemke TL (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 1142. ISBN 9780781768795. Archived from the original on 2016-03-04.
^ ^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.
^ ^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.
^ ^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.
^ 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.
^ 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.
^ 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.

[Drugs.com_pregnancy-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.

[AHFS2015-3] ^ ^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.

[Zhu2001-4] 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.

[Joe2012-5] 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.

[WHO21st-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.

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