PROPATYL NITRATE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

PROPATYL NITRATE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

 

Propatyl Nitrate

IUPAC nomenclature

2,2-bis(nitrooxymethyl)butyl nitrate

Classification

  • Organic nitrate antianginal drug

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 269.17 g/mol
2 Physical appearance Solid
3 Melting point 51.5oC
4 Solubility N/A
5 Octanol/water partition coefficient N/A
5 Presence of ring Not present
6 Number of chiral centers Not present

 

 

Mechanism of Action

i. Like other organic nitrates, propatyl nitrate releases NO.

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 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

Nitration of trimethylolpropane produces Propatyl nitrate. [1]

 

Medicinal Uses

Propatyl nitrate is an antianginal drug 

 

Side Effects

Side effects of Propatyl nitrate are:

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

 

 

MCQs

Q.1 Which of the following statements are correct related with the physicochemical properties of drug Propatyl nitrate?

I. Molecular weight: 269.17 gm/mol

II. Physical appearance: Oil

III. Melting point: 51.5 oC

a) I, II, III

b) I, II

c) II, III

d) I, III

Q.2 Match the following of the drugs with their correct IUPAC names.

i. Propatyl nitrate A. 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
ii. Esomeprazole B. 2,2-bis(nitrooxymethyl)butyl nitrate
iii. Hydroxyzene C. (S)-(−)-5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3H-benzoimidazole
iv. Cyproheptidine D. (±)-2-(2-{4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl}ethoxy)ethanol

 a) i-B, ii-C, iii-D, iv-A

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

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

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

Q.3 Mechanism of action of drug Propatyl nitrate includes?

I. Release if NO

II. Activation of gunaylate cyclase enzyme

III. Active synthesis of cGMP

IV. Vasoconstriction

a) I, III, IV

b) I, IV

c)I,  II, III

d) I, II, III, IV

Q.4 Correct sequence for True/false for the classification of the drug can be?

  • Propatyl nitrate: Organic nitrate antianginal drug
  • Bethanchol: α-adrenergic blocker
  • Labetolol: ß-adrenergic blocker
  • Chlorazepate: Inhalational anesthetics
  • a) TFFT

b) FFTT

c) FFTF

d) TTTF

Q.5 Which of the following statements related with the SAR of dihydropyridines calcium channel blockers is/are correct?

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

b) Increase in nitric group increases the potency.

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

d) All of the above

Q.6 Type of rings present in the structure of Propatyl nitrate?

I. Dihydropyridine

II. Phenyl

III. Dihydrofuran

IV. Cyclobutane

a) II, IV

b) I , II

c) III, IV

d) None of the above

Q.7 Side effect of drug propatyl nitrate is/are?

a) Weakness

b) Headache

c) Vomiting

d) All of the above

 

 

 

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ANSWERS

1-d

2-a

3-c

4-d

5-d

6-d

7-d

 

 

 

REFERENCES

 

[1] Médard: Meml. Poudres (MPOUAT) 35, 113 (1953).

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