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Revision as of 12:39, 23 January 2012

Tipranavir
Clinical data
Trade namesAptivus
AHFS/Drugs.comMonograph
MedlinePlusa606009
License data
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99.9%
MetabolismHepatic
Elimination half-life5–6 hours
ExcretionFecal
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
CompTox Dashboard (EPA)
ECHA InfoCard100.158.066 Edit this at Wikidata
Chemical and physical data
FormulaC31H33F3N2O5S
Molar mass602.66 g/mol 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
 ☒NcheckY (what is this?)  (verify)

Tipranavir, or tipranavir disodium, is a nonpeptidic protease inhibitor (PI) manufactured by Boehringer-Ingelheim under the trade name Aptivus. It is administered with ritonavir in combination therapy to treat HIV infection and is given as two 250 mg capsules together with 200 mg of ritonavir twice daily.

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] Like lopinavir and atazanavir, it is very potent and is effective in salvage therapy for patients with some drug resistance. However, side effects of tipranavir can be more severe than other anti-retrovirals. Some side effects include intracranial hemorraging[citation needed], hepatitis[4], and diabetes mellitus[citation needed]. The drug has also been shown to cause increases in total cholesterol and triglycerides[citation needed].

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. ^ Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley M (2005). "Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir". Antiviral Res. 68 (1): 27–35. doi:10.1016/j.antiviral.2005.07.003. PMID 16122817.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
  4. ^ "Aptivus (tipranavir) Capsules, 250 mg, Prescribing Information", Boehringer Ingelheim, 2007. Revised February 5, 2007.