Dapsone

Prepared by Group 5:

Rudraksh Joshi
Khushbu Jethwa
Sonali Kadam
Shirish Kadam

 In the early 20th century, it is invented by the German chemist Paul
Ehrlich while working on selective toxicity .

 Dapsone (diamino-diphenyl sulfone)
is a medication most commonly used
in combination with rifampicin and
clofazimine as multidrug therapy
(MDT) for the treatment of
Mycobacterium leprae infections (leprosy).
 Official in IP,BP,USP.

 Substitution of aromatic ring with acetyl
group results in decreased activity,
increased solubility in water and decreased
G.I irritation.

 Replacement of 1 amino group with
nitro,hydroxy or hydroxylamine results in
decreased activity.

 Replacement of both amino groups gives
inactive product(with above).

 Replacement of both amino groups with
aldehyde results in prodrug
formation(eg.glucosulfone sodium).

 Replacement of one of benzene rings with
thiazole resulted in decreased activity.

R.T
2 + Na2S
1-chloro-4-nitrobenzene Sodium sulfide 4,4’-dinitrodiphenyl sulfide

4,4’-dinitrodiphenyl sulfide
4,4’-dinitrodiphenyl sulfone
4,4’-diaminodiphenyl sulfone

1. Absorption
 It is completely absorbed after oral administration

2. Distribution
 Approximately 70% bound to plasma protein. The main
metabolite, monoacetyl dapsone, is nearly 100% protein
bound.

3. Metabolism
Dapsone is acetylated in the liver, the degree of which is
genetically determined.

4 . Elimination
The plasma t1/2 is variable, though often>24hrs
Elimination takes 1-2 weeks or longer
Metabolites are excreted in bile & urine

 Mild haemolytic anaemia
 Gastric intolerance-nausea & anorexia
 methaemoglobinaemia, headache, paresthesias, mental
symptoms & drug fever
 allergic rashes, fixed drug eruption, hypermelanosis,
phototoxicity& rarely exfoliative dermatitis
 Hepatitis & agranulocytosis
 Dapsone reaction/sulfone syndrome

 Hypersensitivity
 more frequent in patients receiving multiple-drug therapy.
 The reaction involves a rash and may also include fever,
jaundice, and eosinophilia.
 In general, these symptoms will occur within the first six
weeks of therapy or not at all, and may be treated by
corticosteroid therapy.

 Mycobacterium leprae infections
(leprosy)./hansen’s disease

 Acne.

 Pneumocystis pneumonia.

 Dermatitis Herpetiformis.

 Toxoplasmosis - Prophylaxis

DISEASE ADULT CHILDREN DAYS

Leprosy - Lepromatous 50-100 mg/day 6-10 mg/day 2-5 years

Leprosy - Tuberculoid 100 mg/day NA 6 months

Dermatitis Herpetiformis 50-300 mg/day NA Life long basis

Pneumocystis Pneumonia 100 mg/day 2 mg/kg/day 14-21 days

Pneumocystis Pneumonia 100 mg/day 2 mg/kg/day Life long basis
Prophylaxis

Toxoplasmosis - Prophylaxis 100 mg/day 2 mg/kg/day Life long basis

TRANSDERMAL DOSE
 Administered transdermally
 As a gel 5% topical acne medication
 available in 3-, 30-, and 60-gram tubes.
 In normal use, 0.5 grams should be administered
to the face per application twice a day.

Molecular Formula (C6H4NH2) 2SO2
Molecular weight 248.30 g/mol
Synonyms 4,4-Sulfonyldianiline; 4,4'-Sulfonylbisbenzenamine;
4-Aminophenyl sulfone; Sulfonyldianiline.
Physical state white crystalline powder.
Melting point 175 - 180 deg C
Odor NA
Specific gravity NA
Solubility insoluble in water , soluble in alcohol.
Vapors density 8.3 mg/ml
Stability Stable under ordinary conditions.

 Before using this medication, consult with your doctor or
pharmacist of all prescription and nonprescription/herbal
products you may use, especially of: folic acid antagonists
(such as pyrimethamine), nitrofurantoin, primaquine.
 This medication may decrease the effectiveness of combination-
type birth control pills.
 This can result in pregnancy.

A reversed-phase high performance liquid
chromatography method is developed to
simultaneously estimate serum
concentrations of dapsone (DDS)
 Mobile phase-mixture of n-heptane ,
ethyl acetate ,methanol,strong ammonia
solution
 Stationary phase-silica gel

 Spectrophotometric determination of
dapsone is also described
 PH-6.98
 λmax=525nm

Thin layer chromatography
Mobile phase-mixture of n-heptane ,
ethyl acetate ,methanol,strong ammonia
solution.
Stationary phase-silica gel

 The need for a more reliable route of administration led to
investigation the possibility of an I.M. dapsone depot
injection.
 To achieve effective blood levels for 3-4 weeks, suspensions
of large dapsone particles in an aqueous vehicle were made.
 Studies in the rat revealed that dapsone-dependent
methaemoglobinaemia could be greatly diminished by the co-
administration of metabolic inhibitors(eg-cimetidine).

MARKETED PRODUCTS

STRENGTH VOLUME PRESENTATION PRICE( Rs.)

Aczone Gel 5%w/w 30g Aczone Gel 46.00

STRENGTH VOLUME PRESENTATION PRICE( Rs.)

Dapsone 25mg 1000 DapsoneTAB(IP) 27.98



 Williams D.et al ,Foye's principles of medicinal chemistry, fifth edition,
Lippincott's Williams & Wilkins
 John H.et al ,Wilson & Gisvolds textbook of organic medical &
pharmaceutical chemistry , eleventh edition ,Lippincott's Williams & Wilkins
 Indian Pharmacopoeia, 2010,Volume I, 1162-1163
 United states Pharmacopoeia,2009,Volume II, 2059-2060
 Moncrief J. Journal of Chromatography B: Biomedical Sciences and
Applications
Volume 654, Issue 1, 18 March 1994, 103:110.
 http://www.rxlist.com
 http:// www.medicinenet.com
 http://www.leprosy-information.org
 http://onlinelibrary.wiley.com

Dapsone

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Dapsone