- Molecular NameDapsone
- SynonymAcedapsone; DADPS; Dapson; dapsone; Dapsonum; DDS; Dds, Diaphenylsulfone; Dds, Pharmaceutical; Diamino-diphenyl sulphone; Diaminodifenilsulfona; Diaminodiphenyl Sulfone; Diaphenylsulfon; Diaphenylsulfone; Diaphenylsulphon; Diaphenylsulphone; Diphenasone; DSS; Metabolite C; N, N'-Diphenyl Sulfondiamide; P-Aminophenyl Sulfone; P, P'-Sulfonyldianiline; P,P-Diaminodiphenyl Sulphone; P,P-Sulfonylbisbenzamine; P,P-Sulfonylbisbenzenamine; P,P-Sulphonylbisbenzamine; P,P-Sulphonylbisbenzenamine; P,P-Sulphonyldianiline; P,P'-Diaminodiphenyl Sulfone; Sulfonyldianiline; Sulphadione; Sulphonyldianiline
- Weight249.29
- Drugbank_IDDB00250
- ACS_NO80-08-0
- Show 3D model
- LogP (experiment)1.304
- LogP (predicted, AB/LogP v2.0)1.68
- pka1.3, 2.5
- LogD (pH=7, predicted)1.64
- Solubility (experiment)0.143 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-2.48
- LogSw (predicted, AB/LogsW2.0)0.3
- Sw (mg/ml) (predicted, ACD/Labs)0.32
- No.of HBond Donors3
- No.of HBond Acceptors4
- No.of Rotatable Bonds2
- TPSA88.77
- StatusFDA approved
- AdministrationN/A
- PharmacologyA pharmacological medication most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). It is also used to treat Pneumocystis carinii pneumonia (PCP) caused by Pneumocystis jiroveci (formerly P. carinii). Dapsone is used in combination with pyrimethamine in the treatment of malaria.
- Absorption_value90.0
- Absorption (description)Slowly and almost completely absorbed after oral administration and widely distributed throughout the body.
- Caco_2N/A
- Bioavailability93.0
- Protein binding73.0
- Volume of distribution (VD)1.0 L/kg
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmHepatic (mostly CYP2E1-mediated). It is acetylated to monoacetyldapsone, the extent of which is genetically determined. It is also metabolised by N-oxidation to mono-N-hydroxydapsone, together with glucuronic acid and sulfate conjugation of dapsone and the metabolites. Enterohepatic recycling occurs.
- Half life22.4 h
- ExcretionAbout 70 to 90% of a dose is excreted in the urine, about 10 to 20% as unchanged drug, about 50% as dapsone conjugates, and about 30% as N-oxidation products (mostly conjugated). Small amounts are eliminated in the faeces. About 30 to 50% of a single dose is excreted in the urine within 24 h and more than 70% in 3 days, but there is wide individual variation.
- Urinary Excretion5~15
- Clerance0.60 ml/min/kg
- ToxicityToxic effects are likely to occur at serum concentrations above 10 mg/L. In 1 case of fatal overdosage, a 22-month-old child died 55 h after ingesting about 5 g of dapsone. The concentrations in the plasma and cerebrospinal fluid were 150 mg/L and 33 mg/L, respectively, 42 h after ingestion. Post-mortem concentrations were: blood 135 mg/L, brain 90 μg/g, liver 165 μg/g, and urine 400 mg/L. [R. Davies,Lancet,1950, 1, 905–906.]
- LD50 (rat)N/A
- LD50 (mouse)N/A