UMIFENOVIR Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses in Influenza

Umifenovir

IUPAC nomenclature

Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-meth yl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate.

 

 Classification

Umifenovir belongs to class fusion inhibitors.

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 477.74  g/mol
2 Physical appearance Solid
3 Melting point 133-137°C
4 Solubility Water solubility is 0.00678 mg/ml
5 Presence of ring Indole, benzene
6 Number of chiral centers Not present
 

 

Mechanism of Action

The drug acts on aromatic residues within the glycoprotein which are important for cellular recognition and fusion. This interfere with clathrin-mediated exocytosis and intracellular trafficking, directly at the plasma membrane itself. This stabilizes the plasma membrane and prevent the entry of virus. [1]

 

Structure Activity Relationship

  • Increasing the size of the group at indoleposition 4 from a dimethylamino group to a piperazine do not dramaticallyimprove binding to H3.
  • Increasing the size of the aromatic ring at position 2 does not generate improved interactions, nor did the addition of a meta-NH2 with respect to the thiol.
  • Binding affinity increases by eightfold when the dimethylamino group at indole position 4 on Arbidol is removed for H3 HA.
  • By attaching a hydroxy group in the meta-position, it would be possible to increase the binding by displacing an ordered water molecule the binding pocket next to Arbidol.

 

Method of synthesis

Formaldehyde, dimethylamine and ethyl-6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate to get Umifenovir.

 

Therapeutic Uses

Umifenovir is used for:

  • Treatment of symptoms of influenza virus.
  • Treatment of hepatitis C
  • Investigation drug for the treatment for COVID-10/SARS-CoV-2 Outbreak

 

Side Effects

Side effects of Umifenovir are:

  • Sensitization of the drug
  • Allergic reactions

 

                                                        MCQ

Q.1 Choose the correct statements related to the physicochemical properties of drug umifenovir-

I. Molecular weight is 477.74 gm/mol

II. Present in solid form

III. It is very soluble in water

IV. Melting point is 273K 

a) I, II

b) I, III

c) III, IV

d) I, III, IV

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

i. Umifenovir A. Topotel
ii. Daunorubicin B. Arbidol
iii. Topotecan C. Dacmozen
iv. Dactinomycin D. Myeleran

 a) i-B, ii-C, iii-D, iv-A

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

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

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

Q.3 Umifenovir do not let the virus to?

a) Use the host machinery

b) Infect other cells

c) Grow in size

d) Synthesize DNA

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

  • Umifenovir: Neuraminidase inhibitor analogue
  • Cidofovir: Nonnucleoside reverse transcriptase inhibitor
  • Ribavirin: Conventional nucleoside analogue
  • Tipranavir: HIV protease inhibitor

a) TTTT

b) TTTF

c) FTTT

d) TFTT

Q.5 When the dimethylamino group at indole position-4 arbidol is removed?

a) Biding affinity increases

b) Activity of drug increases

c) Biovailability increases

d) Activity decreases

Q.6 Type/s of ring present in the structure of Umifenovir?

I. Cyclopentyle

II. Indole

III. Benzene

a) II, III

b) I, II

c) I

d) I, II, III 

Q.7 Side effect of drug Umifenovir?

a) Allergic reactions

b) Hallucinations

c) Confusion

d) All of the above

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ANSWERS

1-a

2-b

3-b

4-d

5-a

6-a

7-a

 

REFERENCES

[1] Boriskin YS, Leneva IA, Pecheur EI, Polyak SJ. Arbidol: a broad-spectrum antiviral compound that blocks viral fusion. Current medicinal chemistry. 2008 Apr 1;15(10):997-1005.

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