medicinal diuretics by waris nawaz
TRANSCRIPT
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DIURETICS
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Diuretics (“water pills”) are the drugs which
increase the urine out put (or) urine volume .
What is natreuretic agent ?
Any drug when introduce into the body
increases the out put of sodium
ie., loss of sodium in urine.
DIURETICS
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General knowledge about kidney
1 cardiac output -5 lit/min.
Out of that 20% goes to kidneys i.e.1 lit/min.
Only 20% can enter into glomerelus that is 120 ml.
This 120 ml/min makes glomerular filtrate.
98 Percent water and electrolyte reabsorb
1-2 percent urine formation
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Approximately 1200 ml of blood per minute flows through both kidneys.
Ions such as sodium, chloride,calcium are reabsorbed. Total amount of glucose, amino acids, vitamins,
proteins are reabsorbed. If the urine contains above it represents the disorders. For example proteins such as albumin in higher amounts causes
albuminaria.
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NORMAL PHYSIOLOGY / FUNCTIONS OF KIDNEY
Important functions of the kidney are:-
Water Reabsorption
To maintain a homeostatis balance of electrolytes and water.
To excrete water soluble end products of metabolites.
Filteration
Urine formation
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KIDNEY STRUCTURAL UNIT ---THE NEPHRON
Each kidney contains approximately one million
nephrons and is capable of forming urine
independently.
The nephrons are composed of glomerulus,
proximal tubule, loop of henle, distal tubule.
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NORMAL PHYSIOLOGY OF KIDNEY (URINE FORMATION)
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Diuretics are very effective in the treatment of conditions like:-
chronic heart failure
nephrotic syndrome
chronic hepatic diseases
hypertension
Pregnancy associated oedema
Cirrhosis of the liver.
Therapeutic approaches
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Types of urine
Oliguria
PolyuriaNormal
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CLASSIFICATION OF DIURETICS
Non Mercurial Diuretics Mercurial Diuretics
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CLASSIFICATION OF DIURETICS
A. Weak Diuretics :-
i. Osmotic Diuretics: Electrolytes: Sodium Chloride, Potassium chloride,Mannitol
Nonelectrolytes: Isosorbide, Sucrose, Urea, Glycerol.ii. Xanthine derivatives: Aminophylline, Theophyllineiii. Carbonic anhydrase inhibitors: Acetazolamide,
Dichlorphenamide, Ethozolamide, Methazolamide
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Moderately potent Diuretics:-i. Thiazide Diuretic
Chlorthiazide, Hydrochlorthiazide.Very Potent Diuretics:-
ii. Loop Diuretics: Furosemide, Ethacrynic acid, Torsemide,Bumetamide,
Mercurial: Mersalyl, Mercaptomerin,Meralluride, Chlormerodin, Mercurous chloride (Mersalyl).
Potassium sparing Diuretics:-Triamterene, Spironolactone, Amiloride.
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MERCURAL DIURETICS
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MERCURIAL DIURETICS Mercuric diuretics contains mercuric ion
in their structure and it combine with SH Group containing enzyme and inactivate.
These enzymes control reabsorption of water and Na/Cl Ion exchange.
Block reabsorption of sodium in proximal tubules and Ascending loop of Henle.
They enhance the excretion of potassium.
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MERCURIAL DIURETICS Due to there pronoun and serious
complications not mostly used Merculism Hypersenstivity Excessive diuresis Administered through intramuscular
route and orally less common
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SAR OF MERCURIAL DIURETICS Diuretic activity of mercurial diuretic
require hydrophilic group e.g RCONH attach not less than 3 carbon from Hg.
Compounds with shorter chain activity little or short.
Diuretic activity/toxicity determined by fuctional group attached at X,Y,R Position
Y more , R less activity influence and X not imp activity
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SAR OF MERCURIAL DIURETICS Theophylline instead of X improve
activity Enhanced diuretic activity Reduce tissue irritation Increase absorption from site of
action
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MERALLURIDE
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SYNTHESIS OF MERALLURIDE
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SYNTHESIS OF MERALLURIDE
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USES OF MERALLURIDE EDEMA CHF NEPHROTIC SYNDROME HEPATIC CIRRHOSIS
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MERCAPTOMERIN SODIUM
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SYNTHESIS OF MERCAPTOMERIN SODIUM
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USES OF MERCAPTOMERIN SODIUM
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MERETHOXYLLINE PROCAINE
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NON MERCURIAL DIURETICS
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CLASSIFICATION OF NON MERCURIAL DIURETICS
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THIAZIDE
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SAR OF THIAZIDES
The position 2 can tolerate the presence of small alkyl
groups such as methyl.
Substituents in 3 position determines the
potency,duration of action.
SN
NR1
SO2NH2
R
OO
43
21
87
6
5
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SAR OF THIAZIDES Loss of c-c double bond between 3&4 positions of nucleus
increases diuretic potency approximately three to ten fold.
Direct substitution of the 4,5 or 8 position with an alkyl group
usually results in diminished diuretic activity.
Substitution of the 6-position with an activating group is essential
for diuretic activity . The best substituent's include Cl,Br,CF3 and
No2 groups.
The sulphamoyl group in the7-position is a prerequisite for diuretic
activity.
SN
NR1
SO2NH2
R
OO
43
21
87
6
5
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MECHANISM OF ACTION OF THIAZIDES
These drugs compete for the chloride binding site of the
sodium/chloride symporter and inhibit the re-absorption of
sodium &chloride.
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SYNTHESIS OF CHLORTHIAZIDE
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Uses HEART FAILURE
HYPERTENSION
NEPHROTIC SYNDROMES
Alkalizing the urine.
These are given in combination with amiloride,allopurinol to
prevent the formation of calcium stones in hyper calciuric
patients.
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ADVERSE EFFECTS
GI effects -Anorexia
CNS effects -Dizziness, vertigo.
CVS effects-Ortho static hypotension.
HYPOKALEMIA, HYPONATREMIA,
ALLERGIC REACTIONS
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chlorothiazide R1 =H
hydrochlorothiazide R1=H,R=Cl
trichlormethiazide R1=CHCl2,R=Cl
methyclothiazide R1=CH2Cl,R=Cl
hydroflumethiazide R1=H,R=CF3
DRUGS SUBSTITUENTS
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HYDROCHLOROTHIAZIDE
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CARBONIC ACID INHIBITORS
CH3 C NH
NN
S
S
O
O
N
H
H
O
Acetazolamide
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SAR OF ACETAZOLAMIDE
Presence of sulphonamide moiety necessary for diuretic activity
N group of sulphonamide remain unsubstituted for its activity
If methyl group on N position attachment to retain its activity
CH3 C NH
NN
S
S
O
O
N
H
H
O
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CARBONIC ANHYDRASE INHIBITORS Carbonic anhydrase is present in many
sites but predominent location of this enzyme is the luminal membrane of the proximal tubules cells.
It catalyzes the dehydration of H2CO3 . By blocking Carbonic anhydrase,
inhibitors block sodium bicarbonate reabsorption and cause diuresis.
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MECHANISM OF ACTION OF ACETAZOLAMIDE
It is a sulfonamide derivative which is a non competitive
reversible inhibitor of “carbonic anhydrase enzyme”.
This enzyme is responsible for catalytic reversible hydration of
carbon dioxide and dehydration of carbonic acid.
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MECHANISM OF ACETAZOLAMIDE
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SYNTHESIS OF ACETAZOLAMIDE Reaction between hydrazine hydrate and ammonium
thiocyanate yields 1, 2-bis (thiocarbamoyl) hydrazine which on treatment with phosgene
undergoes molecular rearrangement through loss of ammonia to yield 5-amino-2-mercapto-1, 3, 4-thiadiazole. This on acylation gives a corresponding amide which on oxidation with aqueous chlorine affords the 2-sulphonyl chloride. The final step essentially consists of amidation by treatment with ammonia.
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USES OF ACETAZOLAMIDEHTN, GLUCOMA ,URINARY ALKALINIZATION, ADJUVANT FOR
TREATMENT OF EPILEPSY
ADVERSE EFFECTS: Hypo kalaemia. Renal calculi. Nausea, loss of hearing, loss of apetite, Drowsiness, paresthesia
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LOOP DIURETICS
Loop diuretics selectively inhibit NaCl reabsorption in the thick ascending limb of the loop of
Henle. Due to the large NaCl absorptive capacity of this
segment and the fact that diuresis is not limited by development of acidosis, as it is with the
carbonic anhydrase inhibitors, these drugs are the most efficacious diuretic agents available. The two prototypical drugs of this group are
furosemide and ethacrynic acid
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SYNTHESIS OF FUROSEMIDE
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MECHANISM OF ACTION OF LOOP DIURETICS
These agents produce a peak diuresis much greater than observed
with other commonly used diuretics.
They act by inhibiting the luminal Na/K/2Cl symporter.
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Furosemide is preferred usually to ethacrynic acid for a
number of reasons:
It is less ototoxic.
It has broader dose response curve.
It is more convenient for i.v. use.
It causes fewer git side effects.
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ETHACRYNIC ACID
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SYNTHESIS OF ETHACRYNIC ACID
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USES
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ADVERSE EFFECT OF LOOP DIURETIC
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ALDOSTERONE ANTAGONIST
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Mechanism of action of SPIRONOLACTONE
Aldosterone,by binding to its receptor in the cytoplasm increases
expression &function of Na channel and sodium pump.
Spironolactone competitively inhibits the binding of aldosterone and
abolishes its biological effect.
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O
O
H3C
CH3
O S C CH3
O
Spironolactone-
17-hydroxy-7-α-mercapto-3-oxo-17αpreg-4-ene-21-carboxlic acid-ϒ-lactone
acetate
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POTASSIUM SPARING DIURETIC
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USES Acute renal failure HTN HypokalemiaADVERSE EFFECTS:OtotoxicityHyperuricemiaHypomagnesiaAllergic reactions
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PURINE DIURETICS
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OSMOTIC DIURETIC
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MECHANISM OF ACTION OF OSMOTIC DIURETICS.
Osmotic agents such as Mannitol are low molecular weight
compounds that are freely filtered through bowmans capsule.
They have limited reabsorption because of high water solubility.
Osmotic diuretics increase the volume of water and almost all of
the electrolytes.
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TRIAMTERENE
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SYNTHESIS OF TRIAMETRENE
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DRUG BRAND NAME DOSEAcetazolamide Diamex 125/250mg orallyAmiloride Midamor 5mg orallyBumetanide Bumex 0.5,1,2mg / I.V
0.5mg/2mlFurosemide Lasix 20,40,80mg OR
I.V/I.M 10mg/mlEthacrynic acid Edecrin 25/50mg I.V 50mgChlorothiazide Diuril 250/500mg or
250mg/5ml oral suspens
Hydrochlorthiazide Diucardin 50mg orallyMannitol Osmitrol 5,10,15,20,25% for injSpironolactone Aldactone 25,50,100 mg tabletsTorsemide Demadex 5,10,20,100mg tabletsTriamterene Dyrenium 50/100mg orally
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Medicinal chemistry by Austoshkar www.slideshare.net
Lipponcot’s chapter# 22 diuretic agents
Katzung
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