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Tipranavir

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Title: Tipranavir  
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Tipranavir

Tipranavir
Systematic (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
Clinical data
Trade names Aptivus
AHFS/Drugs.com
MedlinePlus
Licence data EMA:, US FDA:
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Legal status
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability N/D
Protein binding 99.9%
Metabolism Hepatic
Biological half-life 4.8–6 hours
Excretion Feces (82.3%), urine (4.4%)
Identifiers
CAS Registry Number  Y
ATC code J05
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
ChEMBL  N
NIAID ChemDB
PDB ligand ID TPV (, )
Chemical data
Formula C31H33F3N2O5S
Molecular mass 602.66 g/mol
 N   

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.

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.[1]

Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008.[2] 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 may be more severe than those of other anti-retrovirals. Some side effects include intracranial hemorrhage, hepatitis, hyperglycemia and diabetes mellitus. The drug has also been shown to cause increases in total cholesterol and triglycerides.[3]

References

  1. ^ 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.  
  2. ^ "New Aptivus (tipranavir) Oral Solution Approved for Treatment-Experienced Pediatric and Adolescent HIV Patients" (Press release).  
  3. ^ "Aptivus® (tipranavir) capsules 250 mg, oral solution 100 mg/mL, Prescribing Information", Boehringer Inhelheim, 2012. Revised April 2012. [2]
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