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| {{Drugbox| | | __NOTOC__ |
| |IUPAC_name = 4,4'sulfonyldianiline
| | {{Dapsone}} |
| | image=Dapsone.svg
| | {{CMG}}; {{AE}} {{chetan}} |
| | image2=Dapsone3d.png
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| | CAS_number=80-08-0
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| | ATC_prefix=J04
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| | ATC_suffix=BA02
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| | PubChem=2955
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| | DrugBank=APRD00345
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| | C = 12 |H = 12 |N = 2 |O = 2 |S = 1
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| | molecular_weight = 248.302 [[Gram|g]][[Mole (unit)|mol]]<sup>-1</sup>
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| | bioavailability= 70 to 80%
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| | protein_bound = 70 to 90%
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| | metabolism = [[Liver|Hepatic]] (mostly [[CYP2E1]]-mediated)
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| | elimination_half-life= 20 to 30 [[hour]]s
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| | excretion = [[Kidney|Renal]]
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| | pregnancy_AU = B2
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| | pregnancy_US = C
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| | legal_status = ℞-only <small>(U.S.)</small>, [[Prescription drug|POM]] <small>([[United Kingdom|UK]])</small>
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| | routes_of_administration= Oral
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| }} | |
| {{SI}} | |
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| | ==Overview== |
| | '''Dapsone'''(diamino-diphenyl sulphone) is an [[pharmacology|pharmacological]] [[medication]] most commonly used in combination with [[rifampicin]] and [[clofazimine]] as multidrug therapy (MDT) for the treatment of ''[[Mycobacterium leprae]]'' infections ([[leprosy]]). |
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| '''Dapsone'''(diamino-diphenyl sulphone) is an [[pharmacology|pharmacological]] [[medication]] most commonly used in combination with [[rifampicin]] and [[clofazimine]] as multidrug therapy (MDT) for the treatment of ''[[Mycobacterium leprae]]'' infections ([[leprosy]]).
| | ==Category== |
| | Sulfone |
| | ==US Brand Names== |
| | DAPSONE<sup>®</sup> |
| | ==FDA Package Insert== |
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| | ''' [[Dapsone description|Description]]''' |
| | '''| [[Dapsone clinical pharmacology|Clinical Pharmacology]]''' |
| | '''| [[Dapsone microbiology|Microbiology]]''' |
| | '''| [[Dapsone indications and usage|Indications and Usage]]''' |
| | '''| [[Dapsone contraindications|Contraindications]]''' |
| | '''| [[Dapsone warnings and precautions|Warnings and Precautions]]''' |
| | '''| [[Dapsone adverse reactions|Adverse Reactions]]''' |
| | '''| [[Dapsone drug interactions|Drug Interactions]]''' |
| | '''| [[Dapsone overdosage|Overdosage]]''' |
| | '''| [[Dapsone clinical studies|Clinical Studies]]''' |
| | '''| [[Dapsone dosage and administration|Dosage and Administration]]''' |
| | '''| [[Dapsone how supplied|How Supplied]]''' |
| | '''| [[Dapsone labels and packages|Labels and Packages]]''' |
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| == History ==
| | ==Mechanism of Action== |
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| In the early [[20th century]] the [[Germany|German]] chemist [[Paul Ehrlich]] was developing theories of [[selective toxicity]] based largely on the ability of certain [[dye]]s to kill [[microbe]]s. [[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|prontosil red]]. Further investigation into the active chemicals involved led to the discoveries both of dapsone and of the [[Sulfonamide (medicine)|antibacterial sulfonamides]].[http://www.itg.be/itg/DistanceLearning/LectureNotesVandenEndenE/22_Leprosyp14.htm]
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| == Mechanism of action == | |
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| As an [[antibacterial]], dapsone inhibits [[bacteria]]l synthesis of [[dihydrofolic acid]]. Though structurally distinct from dapsone, the sulfonamide group of antibacterial drugs also work in this way. | | As an [[antibacterial]], dapsone inhibits [[bacteria]]l synthesis of [[dihydrofolic acid]]. Though structurally distinct from dapsone, the sulfonamide group of antibacterial drugs also work in this way. |
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| When used for the treatment of skin conditions in which bacteria do not have a role, the mechanism or action of dapsone is less well understood. | | When used for the treatment of skin conditions in which bacteria do not have a role, the mechanism or action of dapsone is less well understood. |
| | ==References== |
| | {{Reflist|2}} |
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| == Indications ==
| | [[Category:Antibiotics]] |
| | | [[Category:Wikinfect]] |
| As well as being used in leprosy dapsone can also be used to treat [[dermatitis herpetiformis]] and other skin conditions including [[lichen planus]]. It is also sometimes used to prevent [[Pneumocystis pneumonia]](PCP) in patients with [[HIV]] and to treat [[idiopathic thrombocytopenic purpura]]. It is used [[prophylaxis|prophylactically]] to prevent [[Pneumocystis pneumonia]] and [[toxoplasmosis]] in patients unable to tolerate [[trimethoprim]] with [[sulfamethoxazole]].<ref name="AMH">Rossi S, ed. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
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| == Administration ==
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| Dapsone is administered orally as a 100mg tablet or alternatively as 25mg tablets.
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| == Adverse effects ==
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| === Effects on the blood ===
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| The most prominent side effects of this drug are dose-related [[hemolysis]] (which may lead to [[hemolytic anemia]]) and [[methemoglobinemia]].<ref>Jopling WH. Side-effects of antileprosy drugs in common use. Lepr Rev 1983; 54: 261–70.</ref> [[Agranulocytosis]] occurs rarely when dapsone is used alone but more frequently in combination regimens for malaria prophylaxis.<ref>Firkin FC, Mariani AF. Agranulocytosis due to dapsone. Med J Aust 1977; 2: 247–51.</ref> Abnormalities in [[white blood cell]] formation, including [[aplastic anaemia]], are rare but the cause of the majority of deaths due to dapsone therapy.<ref>Foucauld J, et al. Dapsone and aplastic anemia. Ann Intern Med 1985; 102: 139.</ref><ref>Meyerson MA, Cohen PR. Dapsone-induced aplastic anaemia in a woman with bullous systemic lupus erythematosus. Mayo Clin Proc 1994; 69: 1159–62.</ref><ref>Björkman A, Phillips-Howard PA. Adverse reactions to sulfa drugs: implications for malaria chemotherapy. Bull WHO 1991; 69: 297–304.</ref>
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| === Effects on the liver ===
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| Toxic [[hepatitis]] and [[cholestatic jaundice]] have been reported by the manufacturer. [[Jaundice]] may also occur as part of the '''dapsone reaction''' or '''dapsone syndrome''' (see below). Dapsone is also known to inhibit the Cytochrome P450 system.
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| === Other adverse effects ===
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| 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.<ref>Jaffuel D, et al. Eosinophilic pneumonia induced by dapsone. BMJ 1998; 317: 181.</ref>
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| === Dapsone reaction ===
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| [[Hypersensitivity]] reactions occur in some patients. This reaction may be more frequent in patients receiving multiple drug therapy.<ref>Richardus JH, Smith TC. Increased incidence in leprosy of hypersensitivity reactions to dapsone after introduction of multidrug therapy. Lepr Rev 1989; 60: 267–73.</ref><ref>Kumar RH, et al. Dapsone syndrome—a five year retrospective analysis. Indian J Lepr 1998; 70: 271–6.</ref><ref>Rao PN, Lakshmi TSS. Increase in the incidence of dapsone hypersensitivity syndrome—an appraisal. Lepr Rev 2001; 72: 57–62.</ref>
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| The reaction always involves a [[rash]] and may also include [[fever]], jaundice, and [[eosinophilia]].<ref>Joseph MS. Hypersensitivity reaction to dapsone. Lepr Rev 1985; 56: 315–20.</ref><ref>Jamrozik K. Dapsone syndrome occurring in two brothers. Lepr Rev 1986; 57: 57–62.</ref><ref>Hortaleza AR, et al. Dapsone syndrome in a Filipino man. Lepr Rev 1995; 66: 307–13.</ref><ref>Tomecki KJ, Catalano CJ. Dapsone hypersensitivity: the sulfone syndrome revisited. Arch Dermatol 1981; 117: 38–9.</ref><ref>Kromann NP, et al. The dapsone syndrome. Arch Dermatol 1982; 118: 531–2.</ref> These symptoms will generally occur within the first six weeks of therapy or not at all, and may be ameliorated by [[corticosteroid]] therapy.<ref name="AMH"> </ref>
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| == Specific considerations ==
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| Certain patients are at higher risks of adverse effects when using dapsone. Some specific issues which should be considered are:<ref name="AMH"> </ref>
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| * Related to the blood (a [[full blood count]] should be obtained prior to initiating therapy):
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| ** [[Porphyria]]
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| ** [[Anaemia]]
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| ** [[Cardiac disease]]
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| ** [[Pulmonary disease]]
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| ** [[HIV]] infection
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| ** [[G6PD deficiency]]
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| * Related to the liver (obtain [[liver function test]]s before starting therapy):
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| ** Liver impairment
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| * Related to [[allergy]]:
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| ** Sulfonamide allergy is associated with dapsone allergy
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| == References ==
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| <div class="references-small"><references/></div>
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| == External links ==
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| *[http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a682128.html MedlinePlus Drug Information]
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| {{Antimycobacterials}}
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| [[Category:Sulfonamide antibiotics]] | |
| [[Category:Leprosy]] | |
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| [[es:Dapsona]]
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| [[fr:Dapsone]]
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| [[no:Dapson]]
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| [[pt:Dapsona]]
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| [[tr:Dapsone]]
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| {{WH}}
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| {{WikiDoc Sources}}
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