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Tipranavir

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tipranavir
Clinical data
Pronunciation/tɪpˈrænəvɪər/
tip-RAN-ə-veer
Trade namesAptivus
AHFS/Drugs.comMonograph
MedlinePlusa606009
License data
Pregnancy
category
Routes of
administration
By mouth (softcapsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99.9%
MetabolismLiver
Eliminationhalf-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
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard(EPA)
ECHA InfoCard100.158.066Edit 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
 ☒NcheckY (what is this?)  (verify)

Tipranavir (TPV), ortipranavir disodium, is a nonpeptidicprotease inhibitor (PI) manufactured byBoehringer Ingelheim under the trade nameAptivus/ˈæptəvəs/AP-tiv-əs. It is administered withritonavir incombination therapy to treatHIV infection.[citation needed]

Tipranavir has the ability to inhibit the replication ofviruses 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.[2] Tipranavir was approved by theFood 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 withritonavir and other antiretroviral drugs, and is not approved for treatment-naïve patients.[1] Likelopinavir andatazanavir, it is very potent and is effective insalvage therapy for patients with drug resistance. However, side effects of tipranavir may be more severe than those of other antiretrovirals. Some side effects includeintracranial hemorrhage,hepatitis,hepatic decompensation,hyperglycemia anddiabetes mellitus. The drug has also been shown to cause increases in totalcholesterol andtriglycerides.[1]

Aptivus labeling has ablack box warning regardinghepatotoxicity and intracranial hemorrhage.[1]

References

[edit]
  1. ^abcd"Aptivus- tipranavir capsule, liquid filled Aptivus- tipranavir solution".DailyMed. 26 June 2020. Retrieved2 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. Retrieved2008-09-02.

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