Tipranavir

Tipranavir
Clinical data
Pronunciation/tɪpˈrænəvɪər/
tip-RAN-ə-veer
Trade namesAptivus (AP-tiv-əs)
AHFS/Drugs.comMonograph
MedlinePlusa606009
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth (soft capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99.9%
MetabolismLiver
Elimination half-life4.8–6 hours
ExcretionFeces (82.3%), urine (4.4%)
Identifiers
  • N-{3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-(2-phenylethyl)-2-propyl-3,4-dihydro-2H-pyran-5-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.158.066 Edit this at Wikidata
Chemical and physical data
FormulaC31H33F3N2O5S
Molar mass602.67 g·mol−1
3D model (JSmol)
  • CCC[C@]1(CC(/O)=C(\C(=O)O1)[C@H](CC)c3cccc(NS(=O)(=O)c2ccc(cn2)C(F)(F)F)c3)CCc4ccccc4
  • InChI=1S/C31H33F3N2O5S/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/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1 checkY
  • Key:SUJUHGSWHZTSEU-FYBSXPHGSA-N checkY
 X markNcheckY (what is this?)  (verify)

Tipranavir (TPV) is a nonpeptidic HIV-1 protease inhibitor manufactured by Boehringer Ingelheim under the trade name Aptivus. It is used as part of combination antiretroviral therapy for treatment-experienced patients with HIV-1 infection whose virus is resistant to more than one protease inhibitor. It is not approved for treatment-naïve patients.

Tipranavir can retain activity against some HIV-1 strains resistant to other protease inhibitors and is indicated for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple protease mutations.

The U.S. Food and Drug Administration (FDA) granted accelerated approval to tipranavir capsules on June 22, 2005. Pediatric use and the oral solution formulation were approved on June 24, 2008, for treatment-experienced pediatric and adolescent patients.

Tipranavir is administered only with ritonavir as a pharmacokinetic enhancer and in combination with other antiretroviral drugs. It is effective in salvage therapy for patients with drug resistance, but its current clinical role is limited by toxicity concerns. Side effects of tipranavir may be more severe than those of other antiretrovirals. Some side effects include intracranial hemorrhage, hepatitis, hepatic decompensation, hyperglycemia and diabetes mellitus. The drug has also been shown to cause increases in total cholesterol and triglycerides.

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.

Tipranavir is currently rarely used, mainly because of intolerance, hepatotoxicity, the need for high-dose ritonavir boosting and the availability of other agents. It is no longer recommended in current guidelines except in unusual salvage contexts.

References

  1. 1 2 3 4 5 "APTIVUS (tipranavir) capsules and oral solution, Full Prescribing Information" (PDF). U.S. Food and Drug Administration. 2020. Retrieved 31 May 2026.
  2. ↑ Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley MG (October 2005). "Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir". Antiviral Research. 68 (1): 27–35. doi:10.1016/j.antiviral.2005.07.003. PMID 16122817.
  3. ↑ "APTIVUS Approval History". U.S. Food and Drug Administration. Retrieved 31 May 2026.
  4. ↑ "New Aptivus (tipranavir) Oral Solution Approved for Treatment-Experienced Pediatric and Adolescent HIV Patients" (Press release). Boehringer Ingelheim. 2008-06-24. Retrieved 2008-09-02.
  5. ↑ Courter JD, Chandra N, Fletcher CV (2010). "Role of tipranavir in treatment of patients with multidrug-resistant HIV". Therapeutics and Clinical Risk Management. 6: 431–441. doi:10.2147/vhrm.s11129. PMC 2952481. PMID 20859543.
  6. ↑ "Archived Drugs: Tipranavir (TPV, Aptivus)". National Institutes of Health. 22 May 2018. Retrieved 31 May 2026.