Question

Provide a brief introduction/background of the molecule Oseltamivir (Tamiflu) and include a brief description of what the molecule is and how the molecule is used. Discuss how does the structure plays a role in its function and why is the shape of the molecule important to its function?

Answer 1

Oseltamivir (Tamiflu)

Structure Of Oseltamivir (Tamiflu)

Brief Description - Oseltamivir is Influenza Neuraminidase Inhibitor (NAI). It is white crystalline solid and with MF C₁₆H₂₈N₂O₄ and molar mass is 312.4 (free ) and 410.4 with phosphate salt (as shown above) .IUPAC nomenclature is 4-acetylamino-5-amino-3(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid, ethyl ester, phosphate where stereochemistry assigned as (3R, 4R, 5S)

Uses-

• Capsules of 30 mg, 45 mg or 75 mg for oral use in phosphate salt form (45 g shell contains gelatin,red iron oxide, titanium dioxide, and yellow iron oxide 45 g contains black iron oxide,    gelatin, and titanium dioxide whereas 75 g shell contains black iron oxide, gelatin, red iron oxide, titanium dioxide, and yellow iron oxide)​
• Powder for oral suspension contains 6 mg/mL as base.

last part is explained on the basis of Structure Activity Relationship (SAR)

The modification of compounds is focused on: carboxylic acid, ester, aldehyde or amide substituted at 1-position of the aromatic ether, and a variety of substituents at 3- or 4-hydroxyl group of aromatic ether

Introduction of the hydrophobic groups in the small hydrophobic pocket could enhance binding action and Asp151 also showed significant favorable electrostatic interaction.

The flexibility of the molecule during the docking calculation permitted turning the tail of the ether chains, thus the steric hindrance of the structure did not have a strong effect in binding with Arg156. Molecular docking studies further supported the aforementioned SAR analysis

Reference for SAR properties-

Studies on Synthesis and Structure-Activity Relationship (SAR) of Derivatives of a New Natural Product from Marine Fungi as Inhibitors of Influenza Virus Neuraminidase  doi:  [10.3390/md9101887]