Tipranavir

Chemical compound
  • EU EMA: by INN
  • US DailyMed: Tipranavir
  • US FDA: Tipranavir
Pregnancy
category
  • AU: B3
Routes of
administrationBy mouth (soft capsules)ATC code
  • J05AE09 (WHO)
Legal statusLegal status
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only[2]
  • EU: Rx-only
Pharmacokinetic dataProtein binding99.9%MetabolismLiverElimination half-life4.8–6 hoursExcretionFeces (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
  • 174484-41-4 checkY
PubChem CID
  • 54682461
DrugBank
  • DB00932 checkY
ChemSpider
  • 10482313 checkY
UNII
  • ZZT404XD09
ChEMBL
  • ChEMBL183041 ☒N
NIAID ChemDB
  • 032941
PDB ligand
  • TPV (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID6048622 Edit this at Wikidata
ECHA InfoCard100.158.066 Edit this at WikidataChemical and physical dataFormulaC31H33F3N2O5SMolar mass602.67 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

Tipranavir (TPV), or tipranavir disodium, is a nonpeptidic protease inhibitor (PI) manufactured by Boehringer Ingelheim under the trade name Aptivus /ˈæptɪvəs/ AP-tiv-əs. It is administered with ritonavir in combination therapy to treat HIV infection.[citation needed]

Tipranavir has the ability to inhibit the replication of viruses that are resistant to other protease inhibitors and is recommended for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple mutations.[3] Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008.[4]

Tipranavir should only be taken in combination with ritonavir and other antiretroviral drugs, and is not approved for treatment-naïve patients.[2] Like lopinavir and atazanavir, it is very potent and is effective in salvage therapy for patients with drug resistance. However, 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.[2]

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.[2]

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c d "Aptivus- tipranavir capsule, liquid filled Aptivus- tipranavir solution". DailyMed. 26 June 2020. Retrieved 2 December 2020.
  3. ^ 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.
  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.

External links

  • "Tipranavir". Drug Information Portal. U.S. National Library of Medicine.
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