atenolol(drug) and its synthesis.pptx

Synthesis of atenolol. There are various methods of synthesis

1. Synthesis of atenolol tanuja 1

2. INTRODUCTION Atenolol is a selective β 1 receptor antagonist, a drug belonging to the group of beta blockers, a class of drug primarily used in cardiovascular diseases. Introduced in 1976, Atenolol was developed as a replacement for propranolol in the treatment of hypertension. It works by slowing down the heart and reducing its workload. 11/2/2017 2

3. HISTORY Dr. James Black 1 st trade name PROPRANALOL PRONETHALOL 11/2/2017 3

4. BETA BLOCKER Beta blocker, also written β -blocker, is a class of medications that are particularly used to manage cardiac arrhythmias, and to protect the heart from a second heart attack (myocardial infarction ) after a first heart attack (i.e. secondary prevention) They are also widely used to treat hypertension. 11/2/2017 4

5. Three known types of beta receptor are β 1, β 2, β 3 receptor. β 1 –adrenergic receptor : are located mainly in the heart and kidney. β 2 – adrenergic receptor : are located mainly in the lungs, gastrointestinal tract , liver, uterus, vascular smooth muscles, and skeletal muscle. β 3 -adrenergic receptor : are located in fat cells. 11/2/2017 5

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7. MEDICINAL USES : The use of beta blocker around time of cardiac surgery decrease the risk of heart dysrhythmias(irregular heart beats). These are given during the congestive heart failure. Hypertension. Long QT syndrome. (disorder of heart electrical activity) Acute myocardial infarction. Ventricle tachycardia. [Fast heart rhythm that starts in the lower part of heart( ventricals)] Supraventricular tachycardia. 11/2/2017 7

8. 11/2/2017 8 SIDE EFFECTS : Dizziness Tiredness Drowsiness Depression Nausea Shortness of breath

9. 11/2/2017 9 Atenolol Structure

10. PROPERTIES OF ATENOLOL IUPAC NAME :- – 2-[4[2-hydroxy -3-(propan-2 ylamino) propoxy] phenyl] acetamide. CAS No.: 29122-68-7 MOLECULAR FORMULA : C 14 H 22 N 2 O 3 MOLECULAR WT : 266.336 g/mol MELTING POINT : 146-148 o C SOLUBILITY :- Freely soluble in methanol , soluble in acetic acid, DMSO, sparingly soluble in 96% ethanol. COLOUR :- white crystalline powder USES :- Anti- adrenergic ( beta-receptor), anti hypertension . 11/2/2017 10

11. org process research development 11/2/2017 11

12. org process Res Dev 1998,2,(4):274 11/2/2017 12

13. J. chem. Pharm.Res.,2012,4(1):375-382 11/2/2017 13

14. Chem pharm bulll1998,46,(3):505 11/2/2017 14

15. SYNTHESIS OF ATENOLOL : proposed work 11/2/2017 15 2-(4-hydroxyphenyl) acetamide

16. IMPURITY Impurity are chemical substances inside a confined amount of liquid, gas, or solid, which differ from the chemical composition of the material or compound. Impurities are either naturally occuring or added during synthesis of a chemical or commercial product. 11/2/2017 16

17. Atenolol impurities by Europian pharmacopeia 11/2/2017 17

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19. Atenolol impurity-G Compound name: atenolol impurity –G(EP) Chemical Name:- 2-[4-(2rs)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]acetic acid.. Molecular formula : C 14 H 21 NO 4 Molecular weight : 267.32 Appearance :- off white solid 11/2/2017 19

20. Retrosynthesis of impurity G 11/2/2017 20

21. Proposed Synthesis:- 11/2/2017 21

22. Atenolol impurity- F COMPOUND NAME:- atenolol impurity -F(EP) CHEMICAL NAME:- 2,2[(1- methylethy)iminobis(2-hydroxypropan-3,1- diyloxy-4,1-phenylene)] diacetamide MOLECULAR FORMULA: -C 25 H 35 NO 6 MOLECULAR WEIGHT:- 473.56 11/2/2017 22

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24. Synthesis of impurity F 11/2/2017 24

25. Experimental work 11/2/2017 25

26. SOLVENT SYSTEM :- 100 % PET ether 11/2/2017 26

27. SOLVENT SYSTEM :- 10% ETHYL ACETATE IN PET ether 11/2/2017 27

28. SOLVENT SYSTEM :- 10% ETHYL ACETATE IN PET ether 11/2/2017 28

29. SOLVENT SYSTEM :- 10% ETHYL ACETATE IN PET ether 11/2/2017 29

30. Thank You 11/2/2017 30 Thank You