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
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.
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