Dapsone

these is readymade ppt for all those who wants to understand dapsone in brief.

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
Ehrlichwhile working on selective toxicity .
Dapsone(diamino-diphenyl sulfone)
is a medication most commonly used
in combination with rifampicinand
clofazimineas 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. 4,4’-dinitrodiphenyl sulfide
4,4’-diaminodiphenyl sulfone
4,4’-dinitrodiphenyl sulfone
2 + Na2S
4,4’-dinitrodiphenyl sulfide 1-chloro-4-nitrobenzene Sodium sulfide
R.T

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. 4 . Elimination
The plasma t
1/2 is variable, though often>24hrs
Elimination takes 1-2 weeks or longer
Metabolites are excreted in bile & urine
3.Metabolism
Dapsone is acetylated in the liver, the degree of which is
genetically determined.

11. Mild haemolyticanaemia
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 rashand 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 -Lepromatous50-100 mg/day6-10 mg/day 2-5 years
Leprosy -Tuberculoid100mg/day NA 6 months
Dermatitis Herpetiformis50-300 mg/day NA Life long basis
Pneumocystis Pneumonia100 mg/day 2 mg/kg/day 14-21 days
Pneumocystis Pneumonia
Prophylaxis
100 mg/day 2 mg/kg/day Life long basis
Toxoplasmosis -Prophylaxis100 mg/day 2 mg/kg/day Life long basis

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

16. Molecular Formula (C
6H
4NH
2)
2SO
2
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
chromatographymethod 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
Spectrophotometricdetermination 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
methaemoglobinaemiacould 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
methaemoglobinaemiacould be greatly diminished by the co-
administration of metabolic inhibitors(eg-cimetidine).

22. STRENGTH VOLUME PRESENTATION PRICE( Rs.)
Aczone Gel5%w/w30g Aczone Gel 46.00
MARKETED PRODUCTS

23. STRENGTH VOLUME PRESENTATION PRICE( Rs.)
Dapsone25mg 1000 DapsoneTAB(IP)27.98
Dapsone50mg 1000 DapsoneTAB(IP)40.85
Dapsone100mg 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