OSELTAMIVIR Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

Oseltamivir

IUPAC nomenclature

Ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)-cyclohex-1-ene-1-carboxylate.

Classification

Oseltamivir is a Neuraminidase inhibitor analogue.

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 312.4  g/mol
2 Physical appearance Solid
3 Melting point 190-206°C
4 Solubility Soluble in water
5 Octanol/water partition coefficient 1
6 Presence of ring Cyclohexene
7 Number of chiral centers 4
 

 

Mechanism of Action

  • Neuraminidase enzyme is necessary for the entry of the virus into new cells.
  • Drug binds with neuraminidase protein and inhibits it which unable the virus to escape from the host cell and infect other cells.

 

Structure Activity Relationship.

  • Oseltamivir sulfonate exhibit stronger binding to avian influenza neuraminidase H5N1 than their carboxylate and phosphate analogues.
  • Alkoxyl ester derivatives have better bioavailability when administered orally.
  • C-4 modified drug having different alkyl chains are most efficient.
  • The C-4 derivatization of drug with thiocarbamates, α-amino acids or cyclic secondary amines led to decreased inhibitory activities.
  • L-aspargine bearing analogues show best results. [1]

 

Method of synthesis

The drug can be synthesized through Roche synthesis without azide as source of nitrogen method. It is a 14 step synthesis method with 89% yield.

 

Therapeutic Uses

Oseltamivir is used for:

  • Treatment of symptoms of influenza virus.
  • Swine Flu Treatment

 

Side Effects

Side effects of Oseltamivir are:

  • Dizziness
  • Increased cough
  • Breathing problems
  • Nausea
  • Vomiting
  • Allergic reactions

 

 MCQ

Q.1 Match the following with correct SAR of the drug Oseltamivir-

i. Alkoxy ester derivatives A. most efficient
ii. C-4 modified drug having different alkyl chains B. Better bioavailability when given orally.
iii. Sulfonates C. stronger binding with influenza
iv.C-4 derivaization with thiocarbamates D. decreased inhibitory effects

 a) i-A, ii-C, iii-B, iv-D

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

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

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

Q.2 Correct sequence for the True/False for correct IUPAC names of the drug can be?

  • Chloraquine: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide.
  • Clobazam: 7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-3H-1,4-benzodiazepine-2-thione
  • Oseltamivir: ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)-cyclohex-1-ene-1-carboxylate
  • Diazepam: (RS)-2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol

a) TFTF

b) TTFF

c) FFFF

d) FFTF

Q.3 Type of ring present in the structure of Oseltamivir drug is?

a) Pyrimidine

b) Purine

c) Benzene

d) None of the above

Q.4 Oseltamivir binds with?

a) Neuraminidase protein

b) α-receptors

c) Nicotinic receptor

d) None of the above

Q.5 Which amongst the following is a therapeutic use of drug Oseltamivir?

a) Treatment of Parkinson’s disease

b) Treatment of insomnia

c) Treatment of influenza

d) Treatment of HIV

Q.6 Which of the following drug and their classification are correct?

I. Oseltamivir: Neuraminidase inhibitor analogue

II. Nelfinavir: Synthetic guanosin neucleoside

III. Foscarnet: Non nucleoside analogue

IV. Lopinavir: HIV protease inhibitor

a) II, III

b) III, I

c) II, IV

d) I, III, IV

Q.7 Octanol/water partition coefficient of Oseltamivir is?

a) 3

b) 2

c) 1

d) -1

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ANSWERS

1-c

2-d

3-d

4-a

5-c

6-d

7-c

 

REFERENCES

[1] Laborda P, Wang SY, Voglmeir J. Influenza neuraminidase inhibitors: synthetic approaches, derivatives and biological activity. Molecules. 2016 Nov;21(11):1513.

 

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