Tipranavir

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.

Tipranavir
Clinical data
Pronunciation/tɪpˈrænəvɪər/ tip-RAN-ə-veer
Trade namesAptivus
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
IUPAC name
  • 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
Chemical and physical data
FormulaC31H33F3N2O5S
Molar mass602.67 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 Y
  • Key:SUJUHGSWHZTSEU-FYBSXPHGSA-N Y
 NY (what is this?)  (verify)

Tipranavir has the ability to inhibit the replication of viruses that are resistant to other protease inhibitors and it recommended for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple mutations.[2] Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008.[3]

Tipranavir should only be taken in combination with ritonavir and other antiretroviral drugs, and is not approved for treatment-naïve patients.[1] 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.[1]

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.[1]

References
  1. "Aptivus- tipranavir capsule, liquid filled Aptivus- tipranavir solution". DailyMed. 26 June 2020. Retrieved 2 December 2020.
  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. "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.
  • "Tipranavir". Drug Information Portal. U.S. National Library of Medicine.
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