Tipranavir

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 300155

CAS#: 174484-41-4

Description: Tipranavir is a nonpeptidic protease inhibitor. 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.


Price and Availability

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10mg
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100mg
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1g
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25mg
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200mg
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2g
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50mg
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500mg
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5g
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Tipranavir, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 2 months after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 300155
Name: Tipranavir
CAS#: 174484-41-4
Chemical Formula: C31H33F3N2O5S
Exact Mass: 602.20623
Molecular Weight: 602.66433
Elemental Analysis: C, 61.78; H, 5.52; F, 9.46; N, 4.65; O, 13.27; S, 5.32


Synonym: PNU-140690; PNU 140690; PNU140690; Tipranavir; brand name: Aptivus.

IUPAC/Chemical Name: N-(3-((R)-1-((R)-6-hydroxy-4-oxo-2-phenethyl-2-propyl-3,4-dihydro-2H-pyran-5-yl)propyl)phenyl)-5-(trifluoromethyl)pyridine-2-sulfonamide

InChi Key: NZPXPXAGXYTROM-FYBSXPHGSA-N

InChi Code: 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/h5-14,18,20,25,36,38H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

SMILES Code: O=S(C1=NC=C(C(F)(F)F)C=C1)(NC2=CC=CC([C@H](C3=C(O)O[C@](CCC)(CCC4=CC=CC=C4)CC3=O)CC)=C2)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO.

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Vergani B, Rusconi S. Tipranavir in the protease inhibitors arena. Drugs R D. 2011 Dec 1;11(4):291-3. doi: 10.2165/11594570-000000000-00000. PubMed PMID: 22133386.

2: Bethell R, Scherer J, Witvrouw M, Paquet A, Coakley E, Hall D. Phenotypic Protease Inhibitor Resistance and Cross-Resistance in the Clinic From 2006‒2008 and Mutational Prevalences in HIV From Patients With Discordant Tipranavir and Darunavir Susceptibility Phenotypes. AIDS Res Hum Retroviruses. 2011 Nov 19. [Epub ahead of print] PubMed PMID: 22098079.

3: Hsieh SM, Chang SY, Hung CC, Sheng WH, Chen MY, Chang SC. Emerging HIV-1 resistance to tipranavir and darunavir in patients with virological failure to first-generation protease inhibitors in Taiwan. Int J STD AIDS. 2011 Nov;22(11):617-20. PubMed PMID: 22096044.

4: Elgadi MM, Piliero PJ. Boosted tipranavir versus darunavir in treatment-experienced patients: observational data from the randomized POTENT trial. Drugs R D. 2011 Dec 1;11(4):295-302. doi: 10.2165/11596340-000000000-00000. PubMed PMID: 22007990.

5: Wang Y, Liu Z, Brunzelle JS, Kovari IA, Dewdney TG, Reiter SJ, Kovari LC. The higher barrier of darunavir and tipranavir resistance for HIV-1 protease. Biochem Biophys Res Commun. 2011 Sep 9;412(4):737-42. Epub 2011 Aug 17. PubMed PMID: 21871444; PubMed Central PMCID: PMC3188455.

6: Allavena C, Flandre P, Pugliese P, Valantin MA, Poizot-Martin I, Cabié A, Melliez H, Cuzin L, Duvivier C, Dellamonica P, Raffi F; Dat'aids Group. Tipranavir in highly antiretroviral treatment-experienced patients: Results from a French prospective cohort. Scand J Infect Dis. 2012 Jan;44(1):37-43. Epub 2011 Aug 19. PubMed PMID: 21851330.

7: Stürmer M, Stephan C, Gute P, Knecht G, Bickel M, Brodt HR, Doerr HW, Gürtler L, Lecocq P, van Houtte M. Comparison of drug resistance scores for tipranavir in protease inhibitor-naive patients infected with HIV-1 B and non-B subtypes. Antimicrob Agents Chemother. 2011 Nov;55(11):5362-6. Epub 2011 Aug 8. PubMed PMID: 21825300; PubMed Central PMCID: PMC3195027.

8: Kort JJ, Aslanyan S, Scherer J, Sabo JP, Kohlbrenner V, Robinson P. Effects of tipranavir, darunavir, and ritonavir on platelet function, coagulation, and fibrinolysis in healthy volunteers. Curr HIV Res. 2011 Jun 1;9(4):237-46. doi: 10.2174/157016211796320306. PubMed PMID: 21671884.

9: Goldwirt L, Braun J, de Castro N, Charreau I, Barrail-Tran A, Delaugerre C, Raffi F, Lascoux-Combe C, Aboulker JP, Taburet AM, Molina JM. Switch from enfuvirtide to raltegravir lowers plasma concentrations of darunavir and tipranavir: a pharmacokinetic substudy of the EASIER-ANRS 138 trial. Antimicrob Agents Chemother. 2011 Jul;55(7):3613-5. Epub 2011 May 16. PubMed PMID: 21576452; PubMed Central PMCID: PMC3122468.

10: Weizsaecker K, Kurowski M, Hoffmeister B, Schürmann D, Feiterna-Sperling C. Pharmacokinetic profile in late pregnancy and cord blood concentration of tipranavir and enfuvirtide. Int J STD AIDS. 2011 May;22(5):294-5. PubMed PMID: 21571982.