ISOSORBIDE DINITRATE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

ISOSORBIDE DINITRATE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

Isosorbide dinitrate

 

IUPAC nomenclature

1,4:3,6-dianhydro-2,5-di-O-nitro-D-glucitol.

Classification

  • Organic nitrate antianginal drug

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 236.14 g/mol
2 Physical appearance Ivory white crystalline powder
3 Melting point 70oC
4 Solubility Freely soluble in acetone
5 Octanol/water partition coefficient 1.31
5 Presence of ring furan
6 Number of chiral centers 4

 

 

Mechanism of Action

i. Isosorbide dinitrate gets convert into Nitric oxide.

ii. Activation of enzyme gunanylate cyclase

iii. Increase in concentration of cGMP within vascular smooth muscles

iv. Vasodilation occurs due to cGMP-dependent protein kinase.

 

Structure Activity Relationship

General structure activity of organic nitrate antianginal drugs can be summarized as:

  • The number of nitrate groups determines the potency of organic nitrate for guanylate cyclase activation.
  • Increase in nitric group increases the potency.
  • Increase in lipophillicity doesn’t have major effect over activation of drug.

 

Method of synthesis

i. Intermolecular dehydration of D-sorbite to give isosorbide using paratoluenesulfonic acid.

ii. Nitration of isosorbide by nitric acid to give isosorbide dinitrate. [1]

 

Medicinal Uses

Isosorbide dinitrate is used for treatment and prevention of:

  • Angina pectoris 

 

Side Effects

Side effects of Isosorbide dinitrate are:

  • Dizziness
  • Headache
  • Flushing
  • Nausea
  • Vomiting
  • Weakness
  • Restlessness
  • Allergic reactions

  

 

MCQs

Q.1 What can be the correct IUPAC nomenclature of Isosorbide dinitrate?

a) 1,4:3,6-dianhydro-2,5-di-O-nitro-D-glucitol.

b) 1,4:3,6-dianhydro-2,5-di-O-nitro-D-propanol.

c) 1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine

d) 1-[(4-Chlorophenyl)(phenyl)methyl]-4-ethyliperazine

Q.2 Which amongst the following statements is/are correct related to the SAR of organic nitrate antianginal drugs?

I. The number of nitrate groups determines the potency of organic nitrate for guanylate cyclase activation.

II. Decreasing nitric group increases the potency.

III. Increase in lipophillicity doesn’t have major effect over activation of drug

a) I, III

b) II, III

c) I, II

d) I, II, III

Q.3 The correct order for the synthesis of drug Isosorbide dinitrate from D-sorbite can be?

I. Intermolecular dehydration

II. Nitration

III. Sulfonation

IV. Sulfonylation

a) I – IV

b) I – II

c) III – II

d) II – IV

Q.4 Side effects of drug isosorbide dinitrate is/are?

a) Headache

b) Allergic reactions

c) Weakness

d) All of the above

Q.5 Match the following drugs with their correct Octanol water partition coefficient-

i. Isosorbide dinitrate A. 1.31
ii. Esomeprazol B. 5.8
iii. Azatadine C. 3.59
iv. Meclizine D. 0.6

 a) i-C, ii-B, iii-A, iv-D

b) i-C, ii-A, iii-D, iv-B

c) i-A, ii-D, iii-C, iv-B

d) i-A, ii-C, iii-B, iv-D

Q.6 An example of drug from class Organic nitrate antianginal drug?

a) Procyclizine

b) Meperidine

c) Alprazolam

d) Isosorbide dinitrate

Q.7 The type of ring system found in the structure of drug isosorbide dinitrate is

a) Dihydroopyridine

b) Furan

c) Phenyl

d) Pyrimidine

 

 

 

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ANSWERS

1-a

2-a

3-b

4-d

5-c

6-d

7-a

 

REFERENCES

[1] Vardanyan R, Hruby V. Synthesis of essential drugs. Elsevier; 2006 Mar 10.

 

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