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Transcript of digoxin
preparation Glycosides Glycosides are any compound containing a carbohydrate molecule (sugar), particularly any such natural product in plants which can be converted by hydrolytic cleavage, into a sugar and a nonsugar component . glycone aglycone or genin The carbohydrate residue is attached by a glycosidic bond at carbon atom 1 (anomeric carbon) to a noncarbohydrate residue . Example cardiac glycosides. cardiac glycosides (Steroidal glycosides) where aglycone part is a steroidal nucleus. Cardiac glycosides are found in a diverse group of plants including Digitalis purpurea and Digitalis lanata (foxgloves) and Strophanthus gratus. such as Ouabain, Digoxin, Digitoxin. digoxin origin A cardiotonic glycoside obtained mainly from
(foxglove) Digitalis lanata. Family: Scrophulariaceae.
Its molecular formula is C41H64O14 molecular weight is 780.95, structure aglycone part tri-digitoxose polysaccharide it consists of three sugars and the aglycone Digoxigenin. odourless white crystal. solubility •practically insoluble in water and in ether •freely soluble in pyridine General meaasures in the extraction of the glycosides 1 .Use a polar solvent , which is mostly alcohol 2. Neutralization of the extract with base 3. Use heat NB:- 1.we cann't using water as solvent due to:- *may induce fermentation *need high boiling point . 2.acid lead to hydrolysis of the glycoside. 3.heat nessesary to inhibit the activity of the hydrolytic enzymes that is present in the plant cell. • The extraction process employs a near-supercritical mixture of CO2 and MeOH to extract the cardiac glycoside • Solvent extraction using ethanol is the most prevalent method. NB:- (Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubilities in two different immiscible liquids, usually water and an organic solvent where it is performed using a separatory funnel) Practical Isolation and Extraction An alcoholic extract of the plant is prepared by maceration powdered leaf in 70% ethanol for 24hr. The macerate then filtered through a sintered glass to yield a clear filtrate. Place the alcoholic extract in a conical flask , and then add lead sub acetate. Mix thoroughly and allow standing. placing the mixture in the centrifuge tubes and decant and take the supernatant i
nto a flasks and add 10% sodium phosphate solution. Mix thoroughly and centrifuge. Now divide the mixture into two divisions: Fraction A Fraction B Take one of the two divisions you made above , and put in a separatory funnel , then shake it with three quantities each of of Chloroform – ethanol ( 3:1 v/v ). Combine the organic extract , then dry by the addition of small quantity of anhydrous sodium sulphate and allow standing for a few minutes. Decants the Chloroform – ethanol extract and reduce the volume on a rotatory evaporator or water bath. Decants the Chloroform – ethanol extract and reduce the volume on a rotatory evaporator or water bath. Cool the hydrolysate and transfer to a separatory funnel , then partition with
three quantities each of Chloroform. Combine the Chloroform extracts and dry with a small quantity of anhydrous sodium sulphate. Decant the Chloroform and reduce the volume on a rotatory evaporator. 1.Baljet's test Fraction A + two drops of picric acid then alkaline with sodium hydroxide solution. Orange to deep red coloration 2. Keller - Killian’s test Fraction A + glacial acetic acid , + 0.1% of ferric chloride sol + concentrated H2SO4 Brown ring on the interface Indication: Pharmacological actions: Pharmacokinetic data: 1.Congestive heart failure. 2.Atrial fibrillation or flutter. •Increase force of contraction of myocardial musle. •Increase stoke volume and cardiac output. Reduce heart rate. Improves circulation, decreases edema, and increases kidney output. Mechanism of action •Digoxin inhibits Na+/K+ ATPase pump in the membranes of heart cells which leads to increase in the level of Na+ in the myocytes,
which leads to a rise in the level of intracellular calcium ions which accounts for positive inotropic effect (increased force of contraction)
Bioavailability: 60 to 80% (Oral) Protein binding : 25% Metabolism : Hepatic Half-life: 36-48 hours Digoxin toxicity: •Arrhythmia •loss of appetite, nausea,
vomiting and diarrhea. •blurred vision,
visual disturbances confusion,
drowsiness, dizziness. NB:- Digoxin has narrow therapeutic index which leads to occurrence of adverse drug reactions. DIGOXIN Take one of the two divisions you made above , and put in a separatory funnel , then shake it with three quantities each of of Chloroform – ethanol ( 3:1 v/v ). Take one of the two divisions you made above , and put in a separatory funnel , then shake it with three quantities each of of Chloroform – ethanol ( 3:1 v/v ). Decants the Chloroform – ethanol extract and reduce the volume on a rotatory evaporator or water bath. Place the other division of the extract in a conical flask, and then add HCl and place in a boiling water bath. Place the other division of the extract in a conical flask, and then add HCl and place in a boiling water bath. Combine the Chloroform extracts and dry with a small quantity of anhydrous sodium sulphate. Decant the Chloroform and reduce the volume on a rotatory evaporator. melt with decomposition
above 230°C. •slightly soluble in diluted (50%) alcohol
and in chloroform