Tamiflu, mechanism

Figure 4.18 The structure of Tamiflu (oseltamivir phosphate), an antiviral agent active against type A influenza, and a molecular model of its minimum-energy conformation, as calculated by molecular mechanics.

Due to the transfer mechanism of TcTS analogous to those of sialidases [25] the prototype of sialidase inhibitors Neu5Ac2en 99 [57] was tested. Compound 99 as well as the potent influenza virus neuraminidase inhibitors zanamivir (Relenza, 100) and the active form of oseltamivir (Tamiflu, 101) with analogous structures of transition state were also of interest as potential inhibitors of TcTS. However, as determined for 99 the TcTS activity was inhibited with only Ki = 12.29 mM (Fig. 15) [33]. 

Many new interest boxes have been added that relate organic chemistry to biology and medicine. Some examples Breast Cancer and Aromatase Inhibitors, Searching for Drugs An Antihistamine, a Nonsedating Antihistamine, and a Drug for Ulcers Diseases Caused by a Misfolded Protein How Tamiflu Works Three Different Antibiotics Act by a Common Mechanism. 

Oseltamivir is an antiviral drug whose phosphate salt is marketed by Hoffmann-La Roche (Basel, Switzerland) under the trade name Tamiflu sold as capsules containing 30 mg, 45 mg, or 75 mg oseltamivir for oral use. It is indicated for the treatment of uncomplicated acute infection caused by influenza A or B virus in patients older than 1 year of age who have been symptomatic for no more than 2 days. Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. ... 

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