[CAS NO. 174484-41-4] Tipranavir

Name: Tipranavir
Brand: Arctom Scientific
SKU: AS239733

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PRODUCTS SPECIFICATIONS [174484-41-4]

Distributor

Catalog

AS239733

Brand

Arctom Scientific

CAS

174484-41-4

DESCRIPTION [174484-41-4]

Overview

MDL	MFCD00949098
Molecular Weight	602.66
Molecular Formula	C31H33F3N2O5S
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

For research use only. We do not sell to patients.

9 Publications Citing Use of MCE

Summary

Tipranavir (PNU-140690) inhibits the enzymatic activity and dimerization of HIV-1 protease , exerts potent activity against multi-protease inhibitor (PI)-resistant HIV-1 isolates with IC ₅₀ s of 66-410 nM ^[1] ^[2] . Tipranavir inhibits SARS-CoV-2 3CL ^pro activity ^[3] .

IC50 & Target

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

In Vitro

Tipranavir (PNU-140690) 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 (HIV _11MIX ), which include HIV _B and HIV _C , is selected against Tipranavir, HIV _11MIX rapidly (by 10 passages [HIV _11MIX ^P10 ]) acquires high-level Tipranavir (PNU-140690) resistance and replicates at high concentrations of Tipranavir (PNU-140690). cHIV _B ^I54V and cHIV _B ^I54V/V82T are significantly resistant to Tipranavir (PNU-140690), with IC ₅₀ s of 2.9 and 3.2 μM, respectively, which are 11- and 12-fold increases in comparison to the IC ₅₀ against cHIV _B , respectively ^[1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Tipranavir (PNU-140690) 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 (PNU-140690) abundance in the liver, spleen, and eyes is significantly higher than that in mice treated with Tipranavir alone. Tipranavir (PNU-140690) metabolites accounts for 31 and 38% in the serum and liver in the Tipranavir-alone group. In Tipranavir (PNU-140690) 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 [ ¹⁴ C]Tipranavir (PNU-140690) 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 ^[2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT02251145	Boehringer Ingelheim	Healthy	May 2002	Phase 1
NCT00144170	Boehringer Ingelheim	HIV Infections	February 2003	Phase 3
NCT02229760	Boehringer Ingelheim	HIV Infections	August 2006	Phase 1\|Phase 2
NCT02259855	Boehringer Ingelheim	Hepatic Insufficiency	January 2006	Phase 1
NCT02226991	Boehringer Ingelheim	Healthy	April 2006	Phase 1
NCT02245451	Boehringer Ingelheim	Healthy	January 2005	Phase 1
NCT00976950	Boehringer Ingelheim	HIV Infections	September 2009
NCT02253849	Boehringer Ingelheim	Healthy	November 2005	Phase 1
NCT02257021	Boehringer Ingelheim	Healthy	February 2005	Phase 1
NCT00275444	Boehringer Ingelheim	HIV Infections	March 2002	Phase 2
NCT02238314	Boehringer Ingelheim	HIV Infections	January 1999	Phase 2
NCT02249416	Boehringer Ingelheim	Healthy	November 2001	Phase 1
NCT00531206	Boehringer Ingelheim	HIV Infections	August 2006
NCT00097799	Boehringer Ingelheim	HIV Infections	December 2004
NCT02243553	Boehringer Ingelheim	Healthy	January 2006	Phase 1
NCT02253875	Boehringer Ingelheim	Healthy	November 2005	Phase 1
NCT00054717	Boehringer Ingelheim	HIV Infections	January 2003	Phase 3
NCT02249442	Boehringer Ingelheim	Hepatic Insufficiency	October 2003	Phase 1
NCT00056641	Boehringer Ingelheim	HIV Infections	January 2003	Phase 2
NCT00530920	Boehringer Ingelheim	HIV Infections	October 2007	Phase 2
NCT02251795	Boehringer Ingelheim	Healthy	August 2007	Phase 1
NCT02251769	Boehringer Ingelheim	Healthy	August 2003	Phase 1
NCT02245269	Boehringer Ingelheim	Healthy	July 2003	Phase 1
NCT02251171	Boehringer Ingelheim	Healthy	August 2003	Phase 1
NCT00805857	Boehringer Ingelheim	HIV Infections	June 2008
NCT02253862	Boehringer Ingelheim	Healthy	December 2005	Phase 1
NCT02251119	Boehringer Ingelheim	Healthy	July 2002	Phase 1
NCT00486330	Yale University\|Boehringer Ingelheim	HIV Infections	May 2006	Not Applicable
NCT02195466	Boehringer Ingelheim	Healthy	June 2003	Phase 1
NCT02253797	Boehringer Ingelheim	Healthy	July 2003	Phase 1
NCT00447902	Boehringer Ingelheim	HIV Infections	March 2007	Phase 3
NCT00933205	Boehringer Ingelheim	HIV Infections	May 2004
NCT00062660	Boehringer Ingelheim	HIV Infections	May 2003
NCT02249130	Boehringer Ingelheim	HIV Infections	March 1999	Phase 2
NCT00146328	Boehringer Ingelheim	HIV Infections	April 2001	Phase 2\|Phase 3
NCT00440271	Boehringer Ingelheim	HIV Infections	February 2007	Phase 3
NCT02244190	Boehringer Ingelheim	Healthy	April 2008	Phase 1
NCT02245438	Boehringer Ingelheim	Healthy	May 2002	Phase 1
NCT00537394	National Institute of Allergy and Infectious Diseases (NIAID)\|AIDS Clinical Trials Group	HIV Infections	January 2008	Phase 3
NCT02253836	Boehringer Ingelheim	Healthy	January 2005	Phase 1
NCT02239835	Boehringer Ingelheim	HIV Infections	December 1999	Phase 2
NCT02226978	Boehringer Ingelheim	Healthy	February 2007	Phase 1
NCT00615290	Boehringer Ingelheim	HIV Infections	June 2007
NCT02251223	Boehringer Ingelheim	HIV Infections	February 2001	Phase 1\|Phase 2
NCT02251158	Boehringer Ingelheim	Healthy	October 2003	Phase 1
NCT00034866	Boehringer Ingelheim	HIV Infections	April 2002	Phase 2
NCT00517192	Boehringer Ingelheim	HIV Infections	September 2007	Phase 3
NCT00192660	Kirby Institute\|St Vincent´s Hospital, Sydney\|National Heart, Lung, and Blood Institute (NHLBI)	HIV-Associated Lipodystrophy Syndrome\|Cardiovascular Disease	February 2003	Phase 4

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 200 mg/mL ( 331.86 mM ; Need ultrasonic)

Ethanol : ≥ 50 mg/mL ( 82.97 mM )

* "≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	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

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: 5 mg/mL (8.30 mM); Suspended solution; Need ultrasonic
2.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 5 mg/mL (8.30 mM); Clear solution
3.

Add each solvent one by one: 10% EtOH >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: 2.5 mg/mL (4.15 mM); Suspended solution; Need ultrasonic
4.

Add each solvent one by one: 10% EtOH >> 90% (20% SBE-β-CD in saline)

Solubility: 2.5 mg/mL (4.15 mM); Suspended solution; Need ultrasonic
5.

Add each solvent one by one: 10% EtOH >> 90% corn oil

Solubility: ≥ 2.5 mg/mL (4.15 mM); Clear solution
6.

Add each solvent one by one: 5% DMSO >> 40% PEG300 >> 5% Tween-80 >> 50% saline

Solubility: 2.5 mg/mL (4.15 mM); Suspended solution; Need ultrasonic

* All of the co-solvents are available by MCE.

References

Synonyms

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*)]-

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

U 140690

PNU 140690

Tipranavir

Aptivus

TPV