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QuickView for Tipranavir (compound)

Name: tipranavir
PubChem Compound ID: 133089
Molecular formula: C31H33F3N2O5S
Molecular weight: 602.665 g/mol
Tipranavir isomer; 2-Pyridinesulfonamide, N-(3-((1S)-1-((6R)-5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl)propyl)phenyl)-5-(trifluoromethyl)-; 2-Pyridinesulfonamide, N-(3-(1-(5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl)propyl)phenyl)-5-(trifluoromethyl)-, (R-(R*.S*))-; 2-Pyridinesulfonamide, N-[3-[(1S)-1-[(6R)-5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-; 174590-27-3; U-141166; AIDS-007998; (R-(R*,S*))-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; Tipranavir analog 17; AIDS007998
Name: tipranavir
Name (isomeric): DB00932
Drug Type: small molecule
Brand: Aptivus, Aptivus (Boehringer Ingelheim)
Category: HIV Protease Inhibitors, Anti-HIV Agents
CAS number: 174484-41-4
Indication: For combination antiretroviral treatment of HIV-1 infected adult patients with evidence of viral replication, who are highly treatment-experienced or have HIV-1 strains resistant to multiple protease inhibitors.
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...
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Mechanism 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 hyd...
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Absorption: Absorption is limited, although no absolute quantification of absorption is available.
Protein binding: Extensive (> 99.9%), to both human serum albumin and α-1-acid glycoprotein.
Biotransformation: Hepatic. In vitro metabolism studies with human liver microsomes indicated that CYP 3A4 is the predominant CYP enzyme involved in tipranavir metabolism.
Half Life: 5-6 hours
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.
Affected organisms: Human Immunodeficiency Virus
Drug interaction:
FosamprenavirTipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Fosamprenavir. Consider alternate therapy.
FluconazoleFluconazole may increase the serum concentration of Tipranavir. Dose adjustments are not required.
MidazolamTipranavir, co-administered with Ritonavir, may increase the plasma concentration of Midazolam. Concomitant therapy is contraindicated.
ClorazepateTipranavir may decrease the metabolism and clearance of Clorazepate. Consider alternate therapy or monitor for Clorazepate toxic effects if Tipranavir is initiated or dose increased.
MestranolMestranol may increase the adverse dermatological effects (i.e. skin rash) of Tipranavir. Tipranavir may decrease the serum concentration Mestranol. Use an alternate form of contraception or monitor for estrogen deficiency if Mestranol is used for hormone replacement therapy.
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