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
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),[1] is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy.[2] 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.[2] Additionally, it has been used for acne, dermatitis herpetiformis, and various other skin conditions.[3] Dapsone is available both topically and by mouth.[4]

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.[2] Common side effects include nausea and loss of appetite.[4] Other side effects include liver inflammation, methemoglobinemia,[5] and a number of types of skin rashes.[2] While the safety of use during pregnancy is not entirely clear some physicians recommend that it be continued in those with leprosy.[2] It is of the sulfone class.[2]

Dapsone was first studied as an antibiotic in 1937.[3] Its use for leprosy began in 1945.[3] It is on the World Health Organization's List of Essential Medicines.[6] The form, which is taken by mouth, is available as a generic drug and not very expensive.[2][7]

Medical uses

Infections

Dapsone is commonly used in combination with rifampicin and clofazimine for the treatment of leprosy.[2] It is also used to both treat and prevent pneumocystis pneumonia (PCP).[2][8] It is also used for toxoplasmosis in people unable to tolerate trimethoprim with sulfamethoxazole.[8]

Dapsone by mouth was one of the first medications used to treat moderate to severe acne vulgaris, and is still occasionally prescribed for the treatment of severe cases.[9][10] A topical form of dapsone is also effective with potentially less side effects.[11]

It is unclear if the combination with pyrimethamine is useful in the prevention of malaria.[12]

Autoimmune disease

  • Cutaneous lupus erythematosis. Dapsone is effective and safe in persons with moderate, severe, or refractory cutaneous lupus erythematosis.[13]
  • Idiopathic thrombocytopenic purpura. Dapsone is effective and safe for adjunctive glucocorticoid-sparing treatment of persons with idiopathic thrombocytopenic purpura and is preferred over danazol or interferon alpha in those people with antinuclear antibodies.[14]
  • Chronic spontaneous urticaria. Dapsone is effective and safe for treatment of second-line therapy for people with chronic spontaneous urticaria in those for whom antihistamines and other first-line agents have failed.[15][16]
  • Relapsing polychondritis. There are no clinical trials but there are many case reports that dapsone is effective at doses of 25 mg/day to 200 mg/day for treatment of relapsing polychondritis.[17]

Other

Dermatitis herpetiformis in combination with a gluten-free diet.[2]

Dapsone may be used to treat brown recluse spider bites that become necrotic.[18]

Dapsone is the recommended treatment for erythema elevatum diutinum, as a review found that using oral dapsone alone was effective in 80% of early cases of the disease. However, dapsone can potentially cause severe side effects, meaning that sometimes steroids or other antibiotics should be used instead, although these alternative treatments are much less effective.[19]

An August 2015 review notes that dapsone is reported to be effective against generalized granuloma annulare.[20]

Dapsone has been used as a monomer in the design of dye adsorbent polymers.[21]

Contraindications and precautions

People with porphyria, anemia, cardiac disease, lung disease, HIV infection, G6PD deficiency, and liver impairment are at higher risks of adverse effects when using dapsone.[8]

Adverse effects

Hypersensitivity reactions occur in 1.4% of persons treated with dapsone, and can be fatal in medical settings with low resources.[22][23] It is a form of severe cutaneous adverse reactions (SCARs) in which a SCARs disorder, primarily the DRESS syndrome or a DRESS syndrome-like reaction occurs.[24][25]

Blood

Hemolysis is the most prominent side-effect, occurring in about 20 % of patients treated with dapsone,[26] although it is dose-related. It may lead to hemolytic anemia and methemoglobinemia.[27] The side-effect is more common and severe in those with glucose-6-phosphate dehydrogenase deficiency, leading to the dapsone-containing antimalarial combination Lapdap being withdrawn from clinical use.[28][29] A case of hemolysis in a neonate from dapsone in breast milk has been reported.[30] Agranulocytosis occurs rarely when dapsone is used alone but more frequently in combination regimens for malaria prophylaxis.[31] Abnormalities in white blood cell formation, including aplastic anemia, are rare, yet are the cause of the majority of deaths attributable to dapsone therapy.[32][33][34]

Methemoglobinemia occurs in about 15 % of patients treated with long-term dapsone at standard doses (100 mg/day). Only special multi-wavelength oximeters (CO-oximeters) can detect methemoglobinemia directly. When there is a "saturation gap" between a low ordinary pulse oximeter reading and a high arterial blood gas analysis result, methemoglobinemia may be suspected.[35]

Liver

Toxic hepatitis and cholestatic jaundice have been reported by the manufacturer. These toxic reactions may also occur as part of the dapsone hypersensitivity syndrome (a form of SCARs-see above) or dapsone syndrome (see below).[24] Dapsone is metabolized by the Cytochrome P450 system, specifically isozymes CYP2D6, CYP2B6, CYP3A4, and CYP2C19.[36] Dapsone metabolites produced by the cytochrome P450 2C19 isozyme are associated with the methemoglobinemia side effect of the drug.

Skin

When used topically, dapsone can cause mild skin irritation, redness, dry skin, burning, and itching. When used together with benzoyl peroxide products, temporary yellow or orange skin discolorations can occur.[37]

Dapsone hypersensitivity syndrome

Hypersensitivity reactions occur in some patients. This reaction may be more frequent in patients receiving multiple-drug therapy.[38][39][40]

The reaction always involves a rash, may also include fever, jaundice, and eosinophilia, and is likely to be one manifestation of the SCARs reaction viz., the DRESS syndrome (see above).[24][41][42][43][44][45] In general, these symptoms will occur within the first six weeks of therapy or not at all, and may be ameliorated by corticosteroid therapy.[8]

Other adverse effects

Other adverse effects include nausea, headache, and rash (which are common), and insomnia, psychosis, and peripheral neuropathy. Effects on the lung occur rarely and may be serious, though are generally reversible.[46]

Mechanism of action

As an antibacterial, dapsone inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthase, thereby inhibiting nucleic acid synthesis.[47] Though structurally distinct from dapsone, the sulfonamide group of antibacterial drugs also work in this way.

As an anti-inflammatory, dapsone inhibits the myeloperoxidase-H2O2-halide-mediated cytotoxic system in polymorphonucleocytes.[48] As part of the respiratory burst that neutrophils use to kill bacteria, myeloperoxidase converts hydrogen peroxide (H
2O
2) into hypochlorous acid (HOCl). HOCl is the most potent oxidant generated by neutrophils, and can cause significant tissue damage during inflammation. Dapsone arrests myeloperoxidase in an inactive intermediate form, reversibly inhibiting the enzyme. This prevents accumulation of hypochlorous acid, and reduces tissue damage during inflammation.[49][50][51][52][53] Myeloperoxidase inhibition has also been suggested as a neuron-sparing mechanism for reducing inflammation in neurodegenerative diseases such as Alzheimer's disease and stroke.[54]

Dapsone's anti-inflammatory and immunomodulatory effects[55] are thought to be its mechanism of action in treating dermatitis herpetiformis.[56]

Dapsone is an odorless white to creamy-white crystalline powder with a slightly bitter taste.

History

Discovery

Synthesis of dapsone from 4-nitrochlorobenzene by E. Fromm and J. Wittmann, 1908[57]

In the early 20th century, the German chemist Paul Ehrlich was developing theories of selective toxicity based largely on the ability of certain dyes to kill microbes. Gerhard Domagk, who would later win a Nobel Prize for his efforts, made a major breakthrough in 1932 with the discovery of the antibacterial prontosil red (sulfonamidochrysoidine). Further investigation into the involved chemicals opened the way to sulfa drug and sulfone therapy, first with the discovery of sulfanilamide, the active agent of prontosil, by Daniel Bovet and his team at Pasteur Institute (1935),[58] then with that of dapsone independently by Ernest Fourneau[59] in France and Gladwin Buttle[60] in the United Kingdom.[61]

Proposed use in antimalarial drugs

The spread of drug-resistant malaria in Africa has encouraged the development of new, low-cost antimalarial drugs. Plasmodium falciparum, one of the Plasmodium species that causes malaria, has developed resistance both to chloroquine and sulfadoxine/pyrimethamine, two of the most common treatments for malaria. Artemisinin, another antimalarial drug, had been developed in the 1980s but was too expensive for large-scale use. This led GlaxoSmithKline to develop Lapdap, a combination drug consisting of chlorproguanil and dapsone. Lapdap was licensed in the United Kingdom starting in October 2003.[29]

One advantage of Lapdap was that chlorproguanil and dapsone are both low-cost drugs. Another was that by virtue of being a combination drug, it was less likely to cause drug resistance. However, because dapsone causes hemolytic anemia in patients with G6PD deficiency, and because G6PD deficiency affects 10-25% of the population of sub-Saharan Africa, it was discovered that Lapdap is not safe for use in Africa. It was available in many African countries for four years before GlaxoSmithKline took it off the market in February 2008.[29]

Dapsone gel

Dapsone had been reported in a few cases to effectively treat acne, but the risk of hemolytic anemia kept it from being widely used for this purpose. For many years scientists attempted to develop a topical formulation of dapsone that would be as effective against acne as oral dapsone, but without the hemolysis side effect. This was difficult to accomplish because dapsone is highly insoluble in aqueous solvents. In the early 2000s QLT USA developed Aczone, a 5% dapsone gel that was shown to be effective against acne without causing clinically significant declines in hemoglobin levels, even in subjects with G6PD deficiency.[62] In February 2016, the FDA approved a 7.5% dapsone gel. This higher strength has the advantage of a once-daily application, versus twice-daily application of the 5% formulation.[63]

Other uses

4,4-Diaminodiphenyl sulfone also finds uses as a curing agent for materials like epoxy resins and imine-based vitrimers, applications include in printed circuit boards, adhesives and coatings.[64][65][66] Its use in epoxy systems typically give a resin with a high glass-transition temperature.

See also

  • Promin, a more-soluble derivative

References

  1. ↑ Lemke TL (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 1142. ISBN 9780781768795. Archived from the original on 2016-03-04.
  2. 1 2 3 4 5 6 7 8 9 10 "Dapsone (Systemic) Monograph for Professionals". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-12. Retrieved January 12, 2015.
  3. 1 2 3 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.
  4. 1 2 Gallant JE (2008). Johns Hopkins HIV Guide 2012. Jones & Bartlett Publishers. p. 193. ISBN 9781449619794. Archived from the original on 2016-03-04.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. 1 2 3 4 Rossi S (2006). Rossi S (ed.). Australian Medicines Handbook. Adelaide. ISBN 0-9757919-2-3.{{cite book}}: CS1 maint: location missing publisher (link)
  9. ↑ Ross CM (October 1961). "The treatment of acne vulgaris with dapsone". The British Journal of Dermatology. 73 (10): 367–370. doi:10.1111/j.1365-2133.1961.tb14398.x. PMID 14494150. S2CID 36293895.
  10. ↑ "Dapsone and Acne Vulgaris". ScienceOfAcne.com. 2012-10-10. Archived from the original on 2012-07-29. Retrieved 2012-08-17.
  11. ↑ Pickert A, Raimer S (June 2009). "An evaluation of dapsone gel 5% in the treatment of acne vulgaris". Expert Opinion on Pharmacotherapy. 10 (9): 1515–1521. doi:10.1517/14656560903002097. PMID 19505219. S2CID 11880942.
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  16. ↑ Liang SE, Hoffmann R, Peterson E, Soter NA (2019). "Use of Dapsone in the Treatment of Chronic Idiopathic and Autoimmune Urticaria". JAMA Dermatol. 155 (1): 90–95. doi:10.1001/jamadermatol.2018.3715. PMC 6439569. PMID 30476976.
  17. ↑ Rapini RP, Warner NB (2006). "Relapsing polychondritis". Clin. Dermatol. 24 (6): 482–5. doi:10.1016/j.clindermatol.2006.07.018. PMID 17113965.
  18. ↑ Forks TP (2000). "Brown recluse spider bites". The Journal of the American Board of Family Practice. 13 (6): 415–423. doi:10.3122/15572625-13-6-415. PMID 11117338.
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  20. ↑ Lukács J, Schliemann S, Elsner P (August 2015). "Treatment of generalized granuloma annulare - a systematic review". Journal of the European Academy of Dermatology and Venereology. John Wiley & Sons. 29 (8): 1467–1480. doi:10.1111/jdv.12976. PMID 25651003. S2CID 20884856.
  21. ↑ Khazaei A, Kazem-Rostami M, Zare A, Moosavi-Zare AR, Sadeghpour M, Afkhami A (15 September 2013). "Synthesis, characterization, and application of a triazene-based polysulfone as a dye adsorbent". Journal of Applied Polymer Science. 129 (6): 3439–3446. doi:10.1002/app.39069.
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  25. ↑ Tempark T, Satapornpong P, Rerknimitr P, Nakkam N, Saksit N, Wattanakrai P, Jantararoungtong T, Koomdee N, Mahakkanukrauh A, Tassaneeyakul W, Suttisai S, Pratoomwun J, Klaewsongkram J, Rerkpattanapipat T, Sukasem C (December 2017). "Dapsone-induced severe cutaneous adverse drug reactions are strongly linked with HLA-B*13: 01 allele in the Thai population". Pharmacogenetics and Genomics. 27 (12): 429–437. doi:10.1097/FPC.0000000000000306. PMID 28885988. S2CID 4283457.
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  48. ↑ Galijasevic S (January 2019). "The development of myeloperoxidase inhibitors". Bioorganic & Medicinal Chemistry Letters. 29 (1): 1–7. doi:10.1016/j.bmcl.2018.11.031. PMID 30466896. S2CID 53721156.
  49. ↑ Bozeman PM, Learn DB, Thomas EL (January 1990). "Assay of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase". Journal of Immunological Methods. 126 (1): 125–133. doi:10.1016/0022-1759(90)90020-v. PMID 2154520.
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  54. ↑ Diaz-Ruiz A, Zavala C, Montes S, Ortiz-Plata A, Salgado-Ceballos H, Orozco-Suarez S, et al. (November 2008). "Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats". Journal of Neuroscience Research. 86 (15): 3410–3419. doi:10.1002/jnr.21775. PMID 18615706. S2CID 5837071.
  55. ↑ Begon E, Chosidow O, Wolkenstein P (December 2004). "[Disulone]". Ann Dermatol Venereol (in French). 131 (12): 1062–73. doi:10.1016/S0151-9638(04)93842-2. PMID 15692440.
  56. ↑ Uetrecht JP (1995). "Myeloperoxidase as a generator of drug free radicals". Biochem. Soc. Symp. 61: 163–70. doi:10.1042/bss0610163. PMID 8660393. S2CID 12471553.
  57. ↑ Derivatives of p-Nitrothiophenols, by E. Fromm and J. Wittmann
    Reports of the German Chemical Society Mai–August 1908 Fromm E, Wittmann J (May 1908). "Derivate desp-Nitrothiophenols". Berichte der Deutschen Chemischen Gesellschaft. 41 (2): 2264–2273. doi:10.1002/cber.190804102131.
  58. ↑ Tréfouël JT, Nitti F, Bovet D (23 November 1935). "Activité du p.aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin". Comptes rendus des séances de la Société de biologie et de ses filiales (in French). 120: 756. Archived from the original on 3 January 2017.
  59. ↑ Fourneau E, Tréfouël TJ, Nitti F, Bovet D (1937). "Action antistreptococcique des dérivés sulfurés organiques". Comptes rendus de l'Académie des sciences (in French). 204: 1763. Archived from the original on 2016-02-20.
  60. ↑ Buttle G, Stephenson D, Smith S, Dewing T, Foster G (June 1937). "Treatment of streptococcal infections in mice with 4:4'diamino-dipheni-sulphone". Lancet. 229 (5936): 1331–4. doi:10.1016/S0140-6736(00)75868-5.
  61. ↑ "Leprosy | 14 History of dapsone and dyes". Archived from the original on 2009-02-12. Retrieved 2009-02-24.
  62. ↑ Stotland M, Shalita AR, Kissling RF (June 2009). "Dapsone 5% gel: a review of its efficacy and safety in the treatment of acne vulgaris". American Journal of Clinical Dermatology. 10 (4): 221–227. doi:10.2165/00128071-200910040-00002. PMID 19489655. S2CID 19485887.
  63. ↑ "Aczone (dapsone) 7.5% Gel Prescribing Information" (PDF). Allergan. February 2016. Retrieved 23 June 2016.
  64. ↑ "ECHA dapsone registration dossier".
  65. ↑ "LAPOX ASH-10". 3 June 2017.
  66. ↑ Schoustra SK, Dijksman JA, Zuilhof H, Smulders MM (November 2020). "Molecular control over vitrimer-like mechanics - tuneable dynamic motifs based on the Hammett equation in polyimine materials". Chemical Science. 12 (1): 293–302. doi:10.1039/d0sc05458e. PMC 8178953. PMID 34163597.
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