Small-molecule inhibitor: tipranavir

Name

History: Tipranavir (as PNU-140690) was described in 1997 (Chong & Pagano, 1997; Poppe et al., 1997).
Peptidases inhibited: An inhibitor of the retropepsins of the HIV-1 and HIV-2 viruses (A02.001 and A02.002, respectively), with particular efficacy against some variants of the enzymes that are resistant to other inhibitors (Rusconi et al., 2000; Yeni, 2003; Best & Haubrich, 2006).
Mechanism: Inhibition is reversible.
Pharmaceutical relevance: Has FDA approval for drug use.
DrugBank: DB00932

CID at PubChem: 65027
ChEBI: 474039
Structure
Chemical/biochemical name: N-[3-[(1R)-1-[(6R)-2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3- yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide
Formula weight: 603

Comment: A sulphonamide compound, Tipranavir (Boehringer Ingelheim) has been described as the first non-peptidic retropepsin inhibitor to become available in the United States (Ellis & Ross, 2005).
Reviews: Best & Haubrich (2006)