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Analysis of sulfonamides

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1. ANALYSIS OF SULPHONAMIDES 12/15/20161 VIKAS COLLEGE OF PHARMACY BY @@@ Mr.S @@@ Pharmaceutical Analysis & Quality Assurance, Vikas College Of Pharmacy,…
  • 1. ANALYSIS OF SULPHONAMIDES 12/15/20161 VIKAS COLLEGE OF PHARMACY BY @@@ Mr.S @@@ Pharmaceutical Analysis & Quality Assurance, Vikas College Of Pharmacy, Vissannapeta.
  • 3. Introduction  Sulphonamide is derived from Prontosil,a prodrug that is metabolised invivo by Azoreductase.  Anti bacterial drugs used in the treatment of infections caused by bacteria (gram positive and gram negative bacteria).  Available in the form of tablets, suspensions,parenterals, opthalmic solutions,ointments. 12/15/20163 VIKAS COLLEGE OF PHARMACY
  • 4. Classification 12/15/20164 FOR SYSTEMIC INFECTIO N • Short acting • Intermediate acting • Long acting FOR INTESTINAL INFETIONS • SULPHASALAZI NE • SULPHAGUANIDI NE TOPICAL APPLICATION • SULPHACETAMIDE SODIUM Sulphadiazin e Sulphathiazo le sulphamethoxaz ole sulphadoxi ne VIKAS COLLEGE OF PHARMACY
  • 5. Structures of Sulphonamides 12/15/20165 VIKAS COLLEGE OF PHARMACY
  • 6. Mechanism of action 12/15/20166  Sulfonamides (such as sulfamethoxazole) and diaminopyrimidines (such as trimethoprim) inhibit different enzymes in the biosynthesis of tetrahydrofolate in the bacteria.  Due to the inhibited production of tetrahydrofolate, the bacteria is unable to synthesize the thymidine, and is therefore also unable to produce new DNA or RNA.  This eventually leads to the death of the bacteria. VIKAS COLLEGE OF PHARMACY
  • 7. Mechanism of action 12/15/20167 VIKAS COLLEGE OF PHARMACY
  • 8. Analytical methods for sulfadrugs Titrimetric method : a)Diazotization titration b)Nonaqueous titration c)Argentometric titration UV-spectrophotometry Colorimetry Chromatography Fluorimetry 12/15/20168 VIKAS COLLEGE OF PHARMACY
  • 9. SULPHADIAZINE 12/15/20169  Chemical formula:C12H14N4O2S  IUPAC name:4-amino-N-(4,6- dimethylpyrimidin-2-yl)benzene-1- sulfonamide  Indication :For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.  Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication. VIKAS COLLEGE OF PHARMACY
  • 10. Diazotization  When aromatic primary amines with nuclear –NH2 groups can be determined quantitatively by standard sodium nitrite solution required to convert them into diazonium salts. 12/15/201610 VIKAS COLLEGE OF PHARMACY
  • 11. SULPHATHIAZOLE 12/15/201611  Chemical Formula C9H9N3O2S2  IUPAC Name 4-amino-N- (1,3-thiazol-2-yl)benzene-1- sulfonamide  Indication: effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle. VIKAS COLLEGE OF PHARMACY
  • 12. Non-Aqueous Titrations  For determination of weak acids and weak bases  TYPES a. Acidimetry in non –aqueous titration b. Alkalimetry in non –aqueous titration  The sulfonamides contain weak acid group, so we are using alkalimetry in NAT. In these titration:  Titrants used :Sodium methoxide,potassium methoxide,Lithium methoxide. 12/15/201612 VIKAS COLLEGE OF PHARMACY
  • 13.  Solvents: a. Strong base solvents: n-butyl amine ,Morpholine b. Weak base solvents: DMF,Anhydrous pyridine  Indicators: 1. 0.1N Alkali Methoxide Indicator 2. Thymol Blue Indicator REAGENTS: 1. 0.1N alkali methoxide.Ex:CH3ONa: 12/15/201613 40ml of methanol+50ml of toulene in a dry flask Add the sodium metal completely dissolve add absolute methanol+add50ml of toulene Alternatively add methanol and toulene to get one litre of solution VIKAS COLLEGE OF PHARMACY
  • 14. ASSAY PROCEDURE 12/15/201614 Weigh 20 tablets and grind it 1-2 mg of sulphathiozole+25ml DMF Add 2 drops thymol blue Titrate with sodium methoxide Blue colur(End point)Perform the blank 0.3g of thymol blue 100ml of absolute methanol Thymol blue indicator 2. Thymol blue indicator VIKAS COLLEGE OF PHARMACY
  • 15. Argentometric Titration PRINCIPLE: • Argentometric titration is otherwise known as Precipitation titration • Argentometry involves the use of the standard solution of silver nitrate as the titrant for estimation of the halides(chlorides,bromides & iodides) 12/15/201615 VIKAS COLLEGE OF PHARMACY
  • 16. PROCEDURE 12/15/201616 Take 0.2-0.3g of sulfonamides Dissolve in 0.1 N NaOH solution is adjusted to give blue colour withThymophthalin Volume make upto 50ml with distilled water Add 0.1 n H2SO4 to discharge blue colour Add 25ml of 0.1N AgNO3 Whole mixture is allowed to stand in dark The ppt is collected on double fold filter paper Wash ppt with water Filterate is acidifed with HNO3 Excess AgNO3 is titrated with 0.1N Ammonium thiocyanate Using ferric alum indicator VIKAS COLLEGE OF PHARMACY
  • 17. SULPHAMETHAZINE 12/15/201617  Chemical Formula: C12H14N4O2S  IUPAC Name: 4-amino-N-(4,6- dimethylpyrimidin-2-yl)benzene-1- sulfonamide  Indication:For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections. VIKAS COLLEGE OF PHARMACY
  • 18. UV-Spectrophotometry Estimation of sulfamethazine: 12/15/201618 Take sulfamethazine sample dissolved in dil.H2SO4 Add small amount of resorcinol Absorbance measure at λmax 320 nm. VIKAS COLLEGE OF PHARMACY
  • 19. 12/15/201619  Unknown should be compared with standard of same concentration as the system obeys Beer’s law.  Absorbance measured at 545nm.  Sulfonamide(mg)=Absorbane of sample × standard(mg) absorbance of standard VIKAS COLLEGE OF PHARMACY
  • 20. Colorimetry 12/15/201620 Analysis of sulfa drugs is done by converting primary amino group of sulfonamides into a diazonium salt by diazotisation and later coupling with suitable chromogenic agent to form Azo dye. Automated Colorimetry VIKAS COLLEGE OF PHARMACY
  • 21. 12/15/201621 Chromogenic Reagents 1.Para dimethyl amino benzaldehyde method 2.Diazotisation followed by coupling with BM Reagent 3.α-1,2-naphthaquinone-4-sulphonate sodium(folin’s reagent) 4.Thiobarbituric acid method 5.α-napthol method VIKAS COLLEGE OF PHARMACY
  • 22. PDAB (Para Dimethyl Amino Benzaldehyde) method Drug solution is treated with solution of PDAB under acidic conditions results in formation of AZOMETHINE,a yellow colour chromogen. Measured at λmax :440nm. It is an example of schiff”s base formation 22 R1=H R2=C6H5-N(CH3)2 R3=C6H5SO2NH-R YELLOW SCHIFF’S BASEPDAB 12/15/2016VIKAS COLLEGE OF PHARMACY
  • 24. CHROMATOGRAPHIC METHOD 12/15/201624 • Paper chromatography is most widely used for analysis of sulfa drugs. • The mobile phase used is a mixture of equal volumes (1:1) of 3%NH4OH and n-butanol. PAPER CHROMATOGRAPHY Paper Chromatography VIKAS COLLEGE OF PHARMACY
  • 25. 12/15/201625 • Thin Layer Chromatography is also most widely used for analysis of sulfa drugs in agricultural industries. • Mobile phase is chloroform and tert-butanol in ratio of 80:20 THIN LAYER CHROMATOGRAPHY TLC plates VIKAS COLLEGE OF PHARMACY
  • 26. FLUORIMETRY 12/15/201626 Sulfa drug is diazotised with NaNO2 and form diazonium salt Then it is coupled with 2,4,6Triaminopyridine. The product obtained is subjected to oxidation to produce triazo derivative which has flouresence property and can be analysed by spectro flourimeter Fluorimeter VIKAS COLLEGE OF PHARMACY
  • 27. CONCLUSION I here by conclude that there is a much necessity for the study of analytical methods of Sulphonamides as they are widely used class of drugs as Anti bacterial agents…….. 12/15/201627 VIKAS COLLEGE OF PHARMACY
  • 28. REFERENCES • The Indian Pharmacopoeia1996 • P. D. Sethi, “Quantitative Analysis of Drugs in Pharmaceutical Formulations”,. • B. Morelli, J. Pharm. Biomed. Anal.,1989, 7, 577. • P. B. Issopoulos, Acta. Pharm. Hung.,1992, 6, 3138. • M. Knochen, J. Giglio and B.F. Reis, J. Pharm. Biomed. Anal., 2003, 33, 191. • K.A Connors :Text book of Pharmaceutical Analysis,Third edition,Page no:(62-63 • Higuchi,Beckmman&Hassan :Pharmaceutical Analysis,second editiom,Page no:(137-157) • V.N Rajasekharan,Text book of Pharmaceutical In Organic Chemistry,Page no(126-128) 12/15/201628 VIKAS COLLEGE OF PHARMACY
  • 29. 12/15/201629 VIKAS COLLEGE OF PHARMACY
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