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	monograph
MedlinePlus	a606009
Licence data	EMA:Link, US FDA:link
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Legal status	UK: POM (Prescription only) US: ℞-only
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 Number	174484-41-4 Y
ATC code	J05AE09 (WHO)
PubChem	CID: 65027
DrugBank	DB00932 Y
ChemSpider	10482313 Y
UNII	ZZT404XD09 Y
ChEMBL	CHEMBL183041 N
NIAID ChemDB	032941
PDB ligand ID	TPV (PDBe, RCSB PDB)
Chemical data
Formula	C31H33F3N2O5S
Molecular mass	602.66 g/mol
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, 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.

Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008. 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.