| Synonyms |
PNU-140690; PNU 140690; PNU140690; Aptivus; N-[3-[(1R)-1-[(6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide; 2-Pyridinesulfonamide, N-[3-[(1R)-1-[(6R)-5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-; 2-Pyridinesulfonamide, N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-, [R-(R*,R*)]-; TPV; U 140690 |
| IUPAC Name |
N-[3-[(1R)-1-[(2R)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3H-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide |
| Molecular Weight |
602.67 |
| Molecular Formula |
C31H33F3N2O5S |
| Canonical SMILES |
CCCC1(CC(=C(C(=O)O1)C(CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4 |
| 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 |
| InChIKey |
SUJUHGSWHZTSEU-FYBSXPHGSA-N |
| Boiling Point |
712.3±70.0°C at 760 mmHg |
| Melting Point |
86-89°C |
| Flash Point |
365.1ºC |
| Purity |
≥95% |
| Density |
1.313±0.06 g/cm3 |
| Solubility |
Soluble in Chloroform (Slightly), Methanol (Slightly) |
| Appearance |
White to Pale Yellow Solid |
| Storage |
Store at -20°C |
| Animal Admin |
All mice (2-4 months old) are maintained under a standard 12-h dark and 12-h light cycle with water and chow provided ad libitum. For metabolomic analysis, Tipranavir (40 mg/kg) is administered via ball-tipped gavage needles, and the mice are housed in separate Metabolic cages for 18 h. Urine and feces samples are collected and stored at -20°C for further analysis. For tissue distribution and inhibition studies, three groups of mice are used and are orally treated with Tipranavir (100 mg/kg), RTV (40 mg/kg), and Tipranavir/r (100 mg/kg Tipranavir and 40 mg/kg RTV), respectively. Tissues including the liver, brain, lung, kidney, spleen, and eyes are collected 30 min after treatment and stored at -20°C for further analysis. |
| Complexity |
1050 |
| Exact Mass |
602.20622782 |
| Index Of Refraction |
1.579 |
| In Vitro |
Tipranavir (TPV) inhibits the enzymatic activity of HIV-1 protease, blocks the dimerization of protease subunits, and exerts potent activity against a wide spectrum of wild-type and multi-PI-resistant HIV-1 variants. When a mixture of 11 multi-PI-resistant (but TPV-sensitive) clinical isolates (HIV11MIX), which include HIVB and HIVC, is selected against Tipranavir, HIV11MIX rapidly (by 10 passages [HIV11MIXP10]) acquires high-level Tipranavir resistance and replicates at high concentrations of Tipranavir. cHIVBI54V and cHIVBI54V/V82T are significantly resistant to TPV, with IC50s of 2.9 and 3.2 μM, respectively, which are 11- and 12-fold increases in comparison to the IC50 against cHIVB, respectively. |
| In Vivo |
Tipranavir (TPV) is administered orally twice daily and must be given in combination with low-dose ritonavir (RTV) to boost Tipranavir bioavailability. In Tipranavir/r-cotreated mice, the Tipranavir abundance in the liver, spleen, and eyes is significantly higher than that in mice treated with Tipranavir alone. Tipranavir metabolites accounts for 31 and 38% in the serum and liver in the Tipranavir-alone group. In Tipranavir and Tipranavir (TPV/r)-cotreated mice, only 1 and 2% of metabolites are detected in the serum and liver. Sprague-Dawley rats are administered a single dose of [14C]Tipranavir with coadministration of RTV. The most abundant metabolite in feces is an oxidation metabolite. In urine, no single metabolite is found to be significantly present. |
| PSA |
113.97000 |
| Target |
IC50: 66-410 nM (HIV-1 isolates) |
| Vapor Pressure |
0mmHg at 25°C |
| XLogP3-AA |
7 |
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