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QuickView for Dapsone (compound)


PubChem
Name: Dapsone
PubChem Compound ID: 11128937
Description: A sulfone active against a wide range of bacteria but mainly employed for its actions against MYCOBACTERIUM LEPRAE. Its mechanism of action is probably similar to that of the SULFONAMIDES which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with PYRIMETHAMINE in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
Molecular formula: C12H12N2O2S
Molecular weight: 256.351 g/mol
DrugBank
Identification
Name: Dapsone
Name (isomeric): DB00250
Drug Type: small molecule
Description: A sulfone active against a wide range of bacteria but mainly employed for its actions against MYCOBACTERIUM LEPRAE. Its mechanism of action is probably similar to that of the SULFONAMIDES which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with PYRIMETHAMINE in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
Synonyms:
P,P-Sulfonylbisbenzenamine; P,P'-Diaminodiphenyl Sulfone; N, N'-Diphenyl Sulfondiamide; Dds, Diaphenylsulfone; Diaphenylsulphon; Diphenasone; DDS; Sulfonyldianiline; Sulphonyldianiline; Diaphenylsulfon.
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Brand: Eporal, Croysulphone, Diphone, Novophone, Sulfona, Sumicure S, Croysulfone, Recolip, Sulfanona-Mae, Normet, Sulfadione, Sulfona-Mae, Araldite Ht, Avlosulfon, Sulfon-Mere, ICI, Dubronax, Tarimyl, Udolac, Dimitone, Avlosulphone, Dumitone, Sulfone Ucb, Sulphon-Mere, Avlosulfone
Category: Antimalarials, Anti-Infective Agents, Antimycobacterials, Folic Acid Antagonists, Anti-inflammatory Agents, Leprostatic Agents, Anti-Infectives
CAS number: 80-08-0
Pharmacology
Indication: For the treatment and management of leprosy and dermatitis herpetiformis.
Pharmacology:
Dapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic ...
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Mechanism of Action: Dapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase. The anti-inflammatory action of the drug is unrelated to its antibacterial action and is still not fully understood.
Absorption: Bioavailability is 70 to 80% following oral administration.
Protein binding: 70 to 90%
Biotransformation: Hepatic, mostly CYP2E1-mediated.
Route of elimination: Renal
Half Life: 28 hours (range 10-50 hours)
Toxicity: Overdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary.
Affected organisms: Mycobacteria
Interactions
Food interaction:
Take without regard to meals.
Drug interaction:
MagnesiumFormation of non-absorbable complexes
AluminiumFormation of non-absorbable complexes
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of dapsone by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of dapsone if voriconazole is initiated, discontinued or dose changed.
TrimethoprimIncreased toxicity of both products
RifabutinDecreased levels of dapsone
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Enzymes