Enabled clinical use of an HIV-1 attachment inhibitor through drug delivery

Drug Discovery Today

Volumn 19, Issue 9, 2014, Pages 1288-1293

  Timmins, Peter ^a   Brown, Jonathan ^a   Meanwell, Nicholas A ^a   Hanna, George J ^a   Zhu, Li ^a   Kadow, John F ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 BENZOYL 1 [(4 METHOXY 1H PYRROLO[2,3 B]PYRIDIN 3 YL)OXOACETYL] 2 METHYLPIPERAZINE; ANTIVIRUS AGENT; BMS 448043; BMS 626529; BMS 663068; BMS 663749; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; ORGANOPHOSPHATE; PRODRUG; UNCLASSIFIED DRUG; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT;

ANTIVIRAL ACTIVITY; CLINICAL EFFECTIVENESS; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; REVIEW; BIOAVAILABILITY; CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; HIV INFECTIONS; ISOLATION AND PURIFICATION; MEDICINAL CHEMISTRY; SOLUBILITY;

ANTI-HIV AGENTS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; COMPUTER SIMULATION; DRUG DELIVERY SYSTEMS; DRUG DESIGN; HIV INFECTIONS; HIV-1; HUMANS; PRODRUGS; SOLUBILITY;

EID: 84907858534     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2014.03.025     Document Type: Short Survey

References (25)

1. B. Dau, and M. Holodniy Novel targets for antiretroviral therapy: clinical progress to date Drugs 69 2009 31 50
2. C. Teixeira Viral surface glycoproteins, gp120 and gp41, as potential drug targets against HIV-1: brief overview on quarter of a century past the approval of the first ant-retroviral drug Eur. J. Med. Chem. 48 2011 979 992
3. J. Weber HIV type 1 tropism and inhibitors of viral entry: clinical implications AIDS Rev. 8 2006 60 77
4. Z. Yang Preclinical pharmacokinetics of novel HIV-1 attachment inhibitor BMS-378806 and prediction of its human pharmacokinetics Biopharm. Drug Disp. 26 2005 387 402
5. Z. Yang Utilization of in vitro Caco-2 permeability and liver microsomal half-life screens in discovering BMS-488043, a novel HIV-1 attachment inhibitor with improved pharmacokinetic properties J. Pharm. Sci. 99 2010 2135 2152
6. Y. Xue Quantitative determination of BMS-378806 in human plasma and urine by high-performance liquid chromatography/tandem mass spectrometry J. Sep. Sci. 30 2007 1267 1275
7. S.S. Jambhekar, and P.J. Breen Drug dissolution: significance of physicochemical properties and physiological conditions Drug Discov. Today 18 2013 1173 1184
8. G. Hanna Safety, tolerability and pharmacokinetics (PK) of a novel, small-molecule HIV-1 attachment inhibitor, BMS-488043, after single and multiple oral doses in healthy subjects 11th Conference on Retroviruses and Opportunistic Infections Abstr. 2004 535
9. G.J. Hanna Antiviral activity, pharmacokinetics, and safety of BMS-48803, a novel small-molecule HIV-1 attachment inhibitor, in HIV-1-infected subjects Antimicrob. Agents Chemother. 55 2011 722 728
10. J.F. Kadow Discovery and development of HIV-1 entry inhibitors that target gp120 W.M. Kazmierski, Antiviral Drugs: From Basic Discovery through Clinical Trials 2011 J. Wiley and Sons 149 162
11. P. Timmins, and J. Brown Formulation technology enables the delivery of HIV medicines Ind. Pharm. 40 2013 12 17
12. M.G. Fakes Enhancement of oral bioavailability of an HIV attachment inhibitor by nanosizing and amorphous formulation approaches Int. J. Pharm. 370 2009 167 174
13. M. Tobyn Amorphous drug-PVP dispersions: application of theoretical, thermal and spectroscopic analytical techniques to the study of a molecule with intermolecular bonds in both the crystalline and pure amorphous state J. Pharm. Sci. 98 2009 3456 3468
14. N. Zhou In vivo patterns of resistance to the HIV attachment inhibitor BMS-488043 Antimicrob. Agents Chemother. 55 2011 729 737
15. B. Nowicka-Sans In vitro antiviral characteristics of HIV-1 attachment inhibitor BMS-626529, the active component of the prodrug BMS-663068 Antimicrob. Agents Chemother. 56 2012 3498 3507
16. J.F. Kadow Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment 6. Preclinical and human pharmacokinetic profiling of BMS-663749, a phosphonooxymethyl prodrug of the HIV-1 attachment inhibitor 2-(4-benzoyl-1-peperazinyl)-1-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoethanone (BMS-488043) J. Med. Chem. 55 2012 2048 2056
17. V.J. Stella, and K.W. Nti-Addae Prodrug strategies to overcome poor water solubility Adv. Drug Deliv. Rev. 59 2007 677 694
18. J. Rautio Prodrugs: design and clinical applications Nat. Rev. Drug Discov. 7 2008 255 270
19. Y. Ueda Prodrugs of piperazine and substituted piperidine antiviral agents Bristol-Myers Squibb. 2010 US7745625
20. T. Heimbach Enzyme-mediated precipitation of parent drugs from their phosphate prodrugs Int. J. Pharm. 261 2003 81 92
21. T. Heimbach Absorption rate limit considerations for oral phosphate prodrugs Pharm. Res. 20 2003 848 856
22. J.F. Kadow Discovery of BMS-663068, an HIV attachment inhibitor for the treatment of HIV-1 241st ACS National Meeting & Exposition Abstr. 2011 MEDI29
23. R. Nettles Single and multiple dose pharmacokinetics in non-HIV infected healthy subjects dosed with BMS-663068 12th International Workshop of Clinical Pharmacokinetics of HIV Therapy 2011
24. J. Brown Compartmental absorption modelling and site of absorption studies to determine feasibility of an extended-release formulation of an HIV-1 attachment inhibitor phosphate ester prodrug J. Pharm. Sci. 102 2013 1742 1751
25. R.E. Nettles Pharmacodynamics, safety and pharmacokinetics of BMS-663068, an oral HIV-1 attachment inhibitor in HIV-1-infected subjects J. Infect. Dis. 206 2012 1002 1011