This document summarizes information about the drug dapsone, including: 1. Dapsone was invented in the early 20th century and is commonly used to treat leprosy in combination with other drugs. 2. It is absorbed after oral administration and metabolized in the liver. Common side effects include anemia, nausea, and rashes. 3. Analytical methods like HPLC and spectroscopy can be used to detect and quantify dapsone in samples.

2. Prepared by Group 5:
Rudraksh Joshi
Khushbu Jethwa
Sonali Kadam
Shirish Kadam

3.  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.

4. 4,4’-diaminodiphenylsulfone

5.  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).

6.  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.

7. 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

9. 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.

10. 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

11.  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

12.  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.

13.  Mycobacterium leprae infections
(leprosy)./hansen’s disease
 Acne.
 Pneumocystis pneumonia.
 Dermatitis Herpetiformis.
 Toxoplasmosis - Prophylaxis

14. 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

15. 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.

16. 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.

17.  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.

18. 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

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

20.  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).

21.  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).

22. MARKETED PRODUCTS
STRENGTH VOLUME PRESENTATION PRICE( Rs.)
Aczone Gel 5%w/w 30g Aczone Gel 46.00

23. STRENGTH VOLUME PRESENTATION PRICE( Rs.)
Dapsone 25mg 1000 DapsoneTAB(IP) 27.98
Dapsone 50mg 1000 DapsoneTAB(IP) 40.85
Dapsone 100mg 1000 DapsoneTAB(IP) 70.69

24.  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