Tipranavir

Tipranavir
Clinical data
Pronunciation	/tɪpˈrænəvɪər/ tip-RAN-ə-veer
Trade names	Aptivus
AHFS/Drugs.com	Monograph
MedlinePlus	a606009
License data	EU EMA: by INN; US FDA: Tipranavir;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth (soft capsules)
ATC code	J05AE09 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Protein binding	99.9%
Metabolism	Hepatic
Elimination half-life	4.8–6 hours
Excretion	Feces (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	174484-41-4 ;
PubChem CID	54682461;
DrugBank	DB00932 ;
ChemSpider	10482313 ;
UNII	ZZT404XD09;
ChEMBL	ChEMBL183041 ;
NIAID ChemDB	032941;
PDB ligand	TPV (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6048622 ;
ECHA InfoCard	100.158.066
Chemical and physical data
Formula	C31H33F3N2O5S
Molar mass	602.67 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SUJUHGSWHZTSEU-FYBSXPHGSA-N ;
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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 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.^[4] 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.^[4]

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.^[4]

References

^ "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.
^ 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.
^ "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.
^ ^a ^b ^c "Aptivus (tipranavir) Capsules, Oral Solution. Full Prescribing Information" (PDF). Boehringer Ingelheim Pharmaceuticals, Inc.

[FDA-AllBoxedWarnings-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 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.

[PI-4] "Aptivus (tipranavir) Capsules, Oral Solution. Full Prescribing Information" (PDF). Boehringer Ingelheim Pharmaceuticals, Inc.

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