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Vidya Bharti College of Pharmacy 1
CONTENTS
 Introduction
 Physiology of urine formation
 Classification
• Drugs
• Structure activity relationship
• Mode of action
• Case study of Acetazolamide
 References
Vidya Bharti College of Pharmacy 2
INTRODUCTION
Diuretics are the agents which increase the rate & volume of urine
formation. These agents mainly act on nephrons and promotes the excretion of
excess fluid
These are indicated in the treatment of
1) Edema
2) Hypertention
3) Drug Posioning
Diuretics are very effective in the treatment of conditions like
 Chronic heart failure
 Nephrotic syndrome
 Chronic hepatic disease
 Hypertension
 Cirrhosis of liver 3
Physiologyof urine formation
Vidya Bharti College of Pharmacy 4
Classification
Vidya Bharti College of Pharmacy 5
1.Inhibitors of carbonic anhydrase
2.Benzothiadiazines
3.Sulfamoyl benzoic acid derivatives (high celling
agents)
4.Mercurials
5.Phenoxyacetic acids
6.Osmotic agents
7.Acidifying agents
8.Xanthines
9.Uricosuric diuretics
10.Potassium sparing agents
Carbonic Anhydrase Inhibitors
N N Acetazolamide: N-[5-(aminosulfonyl)-1,3,4-
thiadiazol-2-yl]acetamide
H3COCHN S SO2NH2
Vidya Bharti College of Pharmacy 6
N N Benzolamide: 5-(phenylsulfonylamino)-1,3,4-
thiadiazole-2-sulfonamide
H2NO2S S NHSO2Ph
SAR of Acetazolamide
N N Acetazolamide: N-[5-(aminosulfonyl)-1,3,4-
thiadiazol-2-yl]acetamide
H3COCHN S SO2NH2
1. SAR study reveals the importance of free amide, nitrogen, because
momo & disubstitution at SO2NH2 abolishes activity.
2. N group of sulphonamide remain unsubstituted for its activity.
3. The free SO2NH2 group is necessary to bind with zinc ion in the
enzyme. This drug enzyme complex is reversible type.
Vidya Bharti College of Pharmacy 7
Vidya Bharti College of Pharmacy 8
MODE OF ACTION
 The acteazolamide thus causes loss of Na+, HCO3
- and K+. As a result
of this, there is decrease in extracellular fluid base which causes
metabolic acidosis. This results in loss of diuretic activity, Hence,
acetazolamide is self-limiting diuretic.
Physical And Chemical properties:
Molecular weight of this drug is 222.3g/mol
Description: Acetazolamide appears as a white to yellowish white fine crystalline powder . No order or taste.
Molecular formula: C4H6N4O3S2
.
Solubility:
Sparingly soluble in cold water.
Slightly soluble in alcohol.
Readily soluble in 1N sodium carbonate solution .
Vidya Bharti College of Pharmacy 9
Case Study Of Acetazolamide
History of acetazolamide:
Acetazolamide comes into medical use in 1952.
It is on the world health organization list of essential medicines, The most effective and safe
medicines needed in health system
Common brand names of acetazolamide are Diamox Sequels, Acetazolamide Novaplus,Diacarb.
UV spectroscopy of Acetazolamide :
Vidya Bharti College of Pharmacy 10
• Conclusion:
• The substituent group may not give rise to the absorption of UV radiation
themselves but their presence modifies the absorption of the principle
chromophore.
• The substituent that increase the intensity of absorption, and possible
wavelength are called as auxochrome,typical auxochrome include
methyl,hydroxyl,alkoxy,halogen and amino groups.
Vidya Bharti College of Pharmacy 11
IR Spectroscopy
• Infrared spectroscopy is the spectroscopy that deals with the infrared
region of the EMR spectrum that is light with a longer wavelength and
lower frequency than visible light (400-800nm).
Vidya Bharti College of Pharmacy 12
INFRARED RESIONS RANGE
Near IR 0.8-2.5µm
Mid IR 2.5- 15 µm
Far IR 15 to Onwards
Acetazolamide contains carbonyl group which is to be
detected by the ir spectroscopy.
Carbonyl group is consist of
aldehyde,ketone,acid,ester,amide,acid chloride and
anhydrides.
This group absorbs strongly in the range of 1850-1650cm
• Amides:
• c=o Stretch occurs at approx 1680-1630cm
• N-H stretching primary amide gives two band near 3350 and 3180cm
• N-H Bending occurs around 1640-1550cm for primary and secondary
amides.
Vidya Bharti College of Pharmacy 13
Aldehydes :
• Aldehyde show very strong band for the carbonyl group that appears in the
range of 1740-1725 for simple aliphatic aldehydes.
Vidya Bharti College of Pharmacy 14
IR SPECTRA OF ACETAZOLAMIDE
Vidya Bharti College of Pharmacy 15
Conclusion: From the IR study of Acetazolamide it is concluded that
it contains aldehyde and amides as a functional group.
C---O stretch of aldehyde
C---O stretch of amide
N---H stretch of amide
REFRENCE
1) Essential of Medical Pharmacology By K.D Tripathi
2)Principle of Medicinal Chemistry By Kadam, Mahadik
,Bothara.
3)International pharmacopoeia 9th Edition
4) Spectroscopy
Vidya Bharti College of Pharmacy 16
THANK YOU
Vidya Bharti College of Pharmacy 17

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Diuretic Analysis

  • 1. Vidya Bharti College of Pharmacy 1
  • 2. CONTENTS  Introduction  Physiology of urine formation  Classification • Drugs • Structure activity relationship • Mode of action • Case study of Acetazolamide  References Vidya Bharti College of Pharmacy 2
  • 3. INTRODUCTION Diuretics are the agents which increase the rate & volume of urine formation. These agents mainly act on nephrons and promotes the excretion of excess fluid These are indicated in the treatment of 1) Edema 2) Hypertention 3) Drug Posioning Diuretics are very effective in the treatment of conditions like  Chronic heart failure  Nephrotic syndrome  Chronic hepatic disease  Hypertension  Cirrhosis of liver 3
  • 4. Physiologyof urine formation Vidya Bharti College of Pharmacy 4
  • 5. Classification Vidya Bharti College of Pharmacy 5 1.Inhibitors of carbonic anhydrase 2.Benzothiadiazines 3.Sulfamoyl benzoic acid derivatives (high celling agents) 4.Mercurials 5.Phenoxyacetic acids 6.Osmotic agents 7.Acidifying agents 8.Xanthines 9.Uricosuric diuretics 10.Potassium sparing agents
  • 6. Carbonic Anhydrase Inhibitors N N Acetazolamide: N-[5-(aminosulfonyl)-1,3,4- thiadiazol-2-yl]acetamide H3COCHN S SO2NH2 Vidya Bharti College of Pharmacy 6 N N Benzolamide: 5-(phenylsulfonylamino)-1,3,4- thiadiazole-2-sulfonamide H2NO2S S NHSO2Ph
  • 7. SAR of Acetazolamide N N Acetazolamide: N-[5-(aminosulfonyl)-1,3,4- thiadiazol-2-yl]acetamide H3COCHN S SO2NH2 1. SAR study reveals the importance of free amide, nitrogen, because momo & disubstitution at SO2NH2 abolishes activity. 2. N group of sulphonamide remain unsubstituted for its activity. 3. The free SO2NH2 group is necessary to bind with zinc ion in the enzyme. This drug enzyme complex is reversible type. Vidya Bharti College of Pharmacy 7
  • 8. Vidya Bharti College of Pharmacy 8 MODE OF ACTION  The acteazolamide thus causes loss of Na+, HCO3 - and K+. As a result of this, there is decrease in extracellular fluid base which causes metabolic acidosis. This results in loss of diuretic activity, Hence, acetazolamide is self-limiting diuretic.
  • 9. Physical And Chemical properties: Molecular weight of this drug is 222.3g/mol Description: Acetazolamide appears as a white to yellowish white fine crystalline powder . No order or taste. Molecular formula: C4H6N4O3S2 . Solubility: Sparingly soluble in cold water. Slightly soluble in alcohol. Readily soluble in 1N sodium carbonate solution . Vidya Bharti College of Pharmacy 9 Case Study Of Acetazolamide History of acetazolamide: Acetazolamide comes into medical use in 1952. It is on the world health organization list of essential medicines, The most effective and safe medicines needed in health system Common brand names of acetazolamide are Diamox Sequels, Acetazolamide Novaplus,Diacarb.
  • 10. UV spectroscopy of Acetazolamide : Vidya Bharti College of Pharmacy 10
  • 11. • Conclusion: • The substituent group may not give rise to the absorption of UV radiation themselves but their presence modifies the absorption of the principle chromophore. • The substituent that increase the intensity of absorption, and possible wavelength are called as auxochrome,typical auxochrome include methyl,hydroxyl,alkoxy,halogen and amino groups. Vidya Bharti College of Pharmacy 11
  • 12. IR Spectroscopy • Infrared spectroscopy is the spectroscopy that deals with the infrared region of the EMR spectrum that is light with a longer wavelength and lower frequency than visible light (400-800nm). Vidya Bharti College of Pharmacy 12 INFRARED RESIONS RANGE Near IR 0.8-2.5µm Mid IR 2.5- 15 µm Far IR 15 to Onwards Acetazolamide contains carbonyl group which is to be detected by the ir spectroscopy. Carbonyl group is consist of aldehyde,ketone,acid,ester,amide,acid chloride and anhydrides. This group absorbs strongly in the range of 1850-1650cm
  • 13. • Amides: • c=o Stretch occurs at approx 1680-1630cm • N-H stretching primary amide gives two band near 3350 and 3180cm • N-H Bending occurs around 1640-1550cm for primary and secondary amides. Vidya Bharti College of Pharmacy 13
  • 14. Aldehydes : • Aldehyde show very strong band for the carbonyl group that appears in the range of 1740-1725 for simple aliphatic aldehydes. Vidya Bharti College of Pharmacy 14
  • 15. IR SPECTRA OF ACETAZOLAMIDE Vidya Bharti College of Pharmacy 15 Conclusion: From the IR study of Acetazolamide it is concluded that it contains aldehyde and amides as a functional group. C---O stretch of aldehyde C---O stretch of amide N---H stretch of amide
  • 16. REFRENCE 1) Essential of Medical Pharmacology By K.D Tripathi 2)Principle of Medicinal Chemistry By Kadam, Mahadik ,Bothara. 3)International pharmacopoeia 9th Edition 4) Spectroscopy Vidya Bharti College of Pharmacy 16
  • 17. THANK YOU Vidya Bharti College of Pharmacy 17