Tipranavir

Cat No.:V5337 Purity: ≥98%
Tipranavir (PNU140690; PNU-140690;trade name: Aptivus) is a marketed anti-HIV drug acting as a nonpeptidic multi-protease inhibitor (IC50s = 66-410 nM).
Tipranavir Chemical Structure CAS No.: 174484-41-4
Product category: New16
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
Other Sizes

Other Forms of Tipranavir:

  • Tipranavir-d4 (tipranavir d4)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Tipranavir (PNU140690; PNU-140690; trade name: Aptivus) is a marketed anti-HIV drug acting as a nonpeptidic multi-protease inhibitor (IC50s = 66-410 nM). Tipranavir is able 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.

Biological Activity I Assay Protocols (From Reference)
Targets

IC50: 66-410 nM (HIV-1 isolates)[1]

ln Vitro
Tipranavir (PNU-140690) exhibits strong action against a broad range of wild-type and multi-PI-resistant HIV-1 variants, inhibits the enzymatic activity of HIV-1 protease, and prevents the dimerization of protease subunits. HIV11MIX, a mixture of 11 multi-PI-resistant (but TPV-sensitive) clinical isolates (including HIVB and HIVC), quickly develops high-level Tipranavir (PNU-140690) resistance and replicates at high concentrations of Tipranavir (PNU-140690) after being selected against Tipranavir (by 10 passages [HIV11MIXP10]). With IC50s of 2.9 and 3.2 μM, respectively, which represent 11- and 12-fold increases in comparison to the IC50 against cHIVB, cHIVBI54V and cHIVBI54V/V82T are considerably resistant to Tipranavir (PNU-140690)[1].
ln Vivo
To increase the bioavailability of dipranavir (PNU-140690), it is necessary to combine it with low-dose ritonavir (RTV) when given orally twice a day. The abundance of Tipranavir (PNU-140690) in the liver, spleen, and eyes is considerably higher in Tipranavir/r-cotreated mice than in Tipranavir-treated animals. In the Tipranavir-alone group, 31 and 38% of the serum and liver, respectively, are made up of metabolites of tipranavir (PNU-140690). In the serum and liver of mice cotreated with tipranavir (PNU-140690) and tipranavir (TPV/r), respectively, only 1 and 2% of metabolites are found. One dose of [14C]Tipranavir (PNU-140690) is given to Sprague-Dawley rats in conjunction with RTV. Feces include a lot of oxidation-related metabolites. There isn't a single metabolite that is discovered to be substantially present in urine[2].
Animal Protocol
Mice[2] 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.
References
[1]. Aoki M, et al. Loss of the protease dimerization inhibition activity of tipranavir (TPV) and its association with the acquisition of resistance to TPV by HIV-1. J Virol. 2012 Dec;86(24):13384-96.
[2]. Li F, et al. Metabolism-mediated drug interactions associated with ritonavir-boosted tipranavir in mice. Drug Metab Dispos. 2010 May;38(5):871-8.
[3]. Qi Sun, et al. Bardoxolone and bardoxolone methyl, two Nrf2 activators in clinical trials, inhibit SARS-CoV-2 replication and its 3C-like protease. Signal Transduct Target Ther. 2021 May 29;6(1):212
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C31H33N2O5F3S
Molecular Weight
602.66432
CAS #
174484-41-4
SMILES
O=C1C([C@H](CC)C2=CC=CC(NS(C3=CC=C(C(F)(F)F)C=N3)(=O)=O)=C2)=C(O)C[C@](CCC4=CC=CC=C4)(CCC)O1
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~200 mg/mL (~331.86 mM)
Ethanol :≥ 50 mg/mL (~82.97 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6593 mL 8.2966 mL 16.5931 mL
5 mM 0.3319 mL 1.6593 mL 3.3186 mL
10 mM 0.1659 mL 0.8297 mL 1.6593 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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