Tipranavir Disodium

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Product Details:

  • Product Name: Tipranavir Disodium
  • CAS #: 191150-83-1
  • Mode of Action:

    Tipranavir (TPV) is a non-peptidic HIV-1 protease inhibitor that inhibits the processing of the viral Gag and Gag-Pol polyproteins in HIV-1 infected cells, thus preventing formation of mature virions. Two mechanisms are suggested in regards to the potency of tipranavir: 1. Tipravanir may bind to the active site of the protease enzyme with fewer hydrogen bonds than peptidic protease inhibitors, which results in increased flexibility, allowing it to fit into the active site of the enzyme in viruses that have become resistance to other protease inhibitors. This also enables tipranavir to adjust to amino acid substitutions at the active site. 2. Tipranavir's strong hydrogen bonding interaction with the amide backbone of the protease active site Asp30 may lead to its activity against resistant viruses.

  • Pharmacodynamics:

    Tipranavir is a non-peptidic protease inhibitor (PI) of HIV. Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.

  • Metabolism:

    Hepatic. In vitro metabolism studies with human liver microsomes indicated that CYP 3A4 is the predominant CYP enzyme involved in tipranavir metabolism.

  • Toxicity:

    Oral LD50 in rat is over 5, 000 mg/kg. Side effects include thirst and hunger, unexplained weight loss, increased urination, fatigue, and dry, itchy skin.

  • ATC: J05AE09
  • DrugBank: DB00932 (APRD01306)
  • Formula: C31-H33-F3-N2-O5-S.2Na
  • Molecular Mass: 646.635
  • Synonyms: (R-(R*,R*))-N-(3-(1-(5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl)propyl)phenyl)-5-(trifluoromethyl)-2-pyridinesulfonamide disodium salt, 3'-((1R)-1-((6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-phenethyl-6-propyl-2H-pyran-3-yl)propyl)-5-(trifluoromethyl)-2-pyridinesulfonanilide, disodium salt, PNU 140690E, PNU-140690E, Tipranavir disodium, UNII-9BAN2XG1ZW
  • SMILES: S(c1ncc(C(F)(F)F)cc1)([N-]c1cc([C@H](C=2C(O[C@@](CCc3ccccc3)(CCC)CC2[O-])=O)CC)ccc1)(=O)=O.[Na+].[Na+]
  • AHFS Code: 08:18.08.08
  • InChl: 1S/C31H32F3N2O5S.2Na/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34;;/h5-14,18,20,25H,3-4,15-17,19H2,1-2H3,(H,37,38);;/q-1;2*+1/p-1/t25-,30-;;/m1../s1
  • General Reference:


    1. Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley MG: Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir. Antiviral Res. 2005 Oct;68(1):27-35. Pubmed
    2. Tipranavir: PNU 140690, tipranivir. Drugs R D. 2006;7(1):55-62. Pubmed
    3. Temesgen Z, Feinberg J: Tipranavir: a new option for the treatment of drug-resistant HIV infection. Clin Infect Dis. 2007 Sep 15;45(6):761-9. Epub 2007 Aug 7. Pubmed
    4. Luna B, Townsend MU: Tipranavir: the first nonpeptidic protease inhibitor for the treatment of protease resistance. Clin Ther. 2007 Nov;29(11):2309-18. Pubmed


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