Literature DB >> 17335190

N-(3,3a,4,4a,5,5a,6,6a-Octahydro-1,3-dioxo-4,6- ethenocycloprop[f]isoindol-2-(1H)-yl)carboxamides: Identification of novel orthopoxvirus egress inhibitors.

Thomas R Bailey1, Susan R Rippin, Elizabeth Opsitnick, Christopher J Burns, Daniel C Pevear, Marc S Collett, Gerry Rhodes, Sanjeev Tohan, John W Huggins, Robert O Baker, Earl R Kern, Kathy A Keith, Dongcheng Dai, Guang Yang, Dennis Hruby, Robert Jordan.   

Abstract

A series of novel, potent orthopoxvirus egress inhibitors was identified during high-throughput screening of the ViroPharma small molecule collection. Using structure--activity relationship information inferred from early hits, several compounds were synthesized, and compound 14 was identified as a potent, orally bioavailable first-in-class inhibitor of orthopoxvirus egress from infected cells. Compound 14 has shown comparable efficaciousness in three murine orthopoxvirus models and has entered Phase I clinical trials.

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Year:  2007        PMID： 17335190      PMCID： PMC4067006          DOI： 10.1021/jm061484y

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   8.039


  9 in total

Review 1.  In vitro activity of potential anti-poxvirus agents.

Authors:  Earl R Kern
Journal:  Antiviral Res       Date:  2003-01       Impact factor: 5.970

Review 2.  Discovery of antivirals against smallpox.

Authors:  Stephen C Harrison; Bruce Alberts; Ellie Ehrenfeld; Lynn Enquist; Harvey Fineberg; Steven L McKnight; Bernard Moss; Michael O'Donnell; Hidde Ploegh; Sandra L Schmid; K Peter Walter; Julie Theriot
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-12       Impact factor: 11.205

3.  Intravenous cidofovir for peripheral cytomegalovirus retinitis in patients with AIDS. A randomized, controlled trial.

Authors:  J P Lalezari; R J Stagg; B D Kuppermann; G N Holland; F Kramer; D V Ives; M Youle; M R Robinson; W L Drew; H S Jaffe
Journal:  Ann Intern Med       Date:  1997-02-15       Impact factor: 25.391

4.  Effect of incorporation of cidofovir into DNA by human cytomegalovirus DNA polymerase on DNA elongation.

Authors:  X Xiong; J L Smith; M S Chen
Journal:  Antimicrob Agents Chemother       Date:  1997-03       Impact factor: 5.191

5.  Increased antiviral activity of 1-O-hexadecyloxypropyl-[2-(14)C]cidofovir in MRC-5 human lung fibroblasts is explained by unique cellular uptake and metabolism.

Authors:  Kathy A Aldern; Stephanie L Ciesla; Kristine L Winegarden; Karl Y Hostetler
Journal:  Mol Pharmacol       Date:  2003-03       Impact factor: 4.436

Review 6.  Pathogenesis and potential antiviral therapy of complications of smallpox vaccination.

Authors:  Mike Bray
Journal:  Antiviral Res       Date:  2003-04       Impact factor: 5.970

7.  An orally bioavailable antipoxvirus compound (ST-246) inhibits extracellular virus formation and protects mice from lethal orthopoxvirus Challenge.

Authors:  Guang Yang; Daniel C Pevear; Marc H Davies; Marc S Collett; Tom Bailey; Susan Rippen; Linda Barone; Chris Burns; Gerry Rhodes; Sanjeev Tohan; John W Huggins; Robert O Baker; R L Mark Buller; Erin Touchette; Kem Waller; Jill Schriewer; Johan Neyts; Erik DeClercq; Kevin Jones; Dennis Hruby; Robert Jordan
Journal:  J Virol       Date:  2005-10       Impact factor: 6.549

8.  Smallpox research activities: U.S. interagency collaboration, 2001.

Authors:  James W LeDuc; Inger Damon; David A Relman; John Huggins; Peter B Jahrling
Journal:  Emerg Infect Dis       Date:  2002-07       Impact factor: 6.883

9.  Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections.

Authors:  Robert O Baker; Mike Bray; John W Huggins
Journal:  Antiviral Res       Date:  2003-01       Impact factor: 10.103
  9 in total
  12 in total

1.  Development and Validation of a Method of Liquid Chromatography Coupled with Tandem Mass Spectrometry for Quantification of ST-246 (Tecovirimat) in Human Plasma.

Authors:  Galina A Oleinik; Vladimir V Koval; Svetlana V Usova; Larisa N Shishkina; Alexander A Chernonosov
Journal:  Molecules       Date:  2022-06-02       Impact factor: 4.927

2.  Pharmacokinetic comparison of a single oral dose of polymorph form i versus form V capsules of the antiorthopoxvirus compound ST-246 in human volunteers.

Authors:  Jarasvech Chinsangaram; Kady M Honeychurch; Shanthakumar R Tyavanagimatt; Tove' C Bolken; Robert Jordan; Kevin F Jones; Thomas Marbury; Israel Lichtenstein; Margaret Pickens; Michael Corrado; Patrick Landis; Jean M Clarke; Annie M Frimm; Dennis E Hruby
Journal:  Antimicrob Agents Chemother       Date:  2012-04-23       Impact factor: 5.938

3.  Safety and pharmacokinetics of the antiorthopoxvirus compound ST-246 following repeat oral dosing in healthy adult subjects.

Authors:  Robert Jordan; Jarasvech Chinsangaram; Tove' C Bolken; Shanthakumar R Tyavanagimatt; Deborah Tien; Kevin F Jones; Annie Frimm; Michael L Corrado; Margaret Pickens; Patrick Landis; Jean Clarke; Thomas C Marbury; Dennis E Hruby
Journal:  Antimicrob Agents Chemother       Date:  2010-04-12       Impact factor: 5.938

4.  Tricyclo[3.2.2.0(2,4)]non-8-en-6,7-dicarbonic acid derivatives efficiently inhibits the replication of different orthopoxvirus species.

Authors:  B A Selivanov; E F Belanov; N I Bormotov; S M Balakhnin; O A Serova; V A Svyatchenko; N N Kiselev; E I Kazachinskaya; V B Loktev; A Ya Tikhonov
Journal:  Dokl Biol Sci       Date:  2012-01-07

5.  Safety and pharmacokinetics of the anti-orthopoxvirus compound ST-246 following a single daily oral dose for 14 days in human volunteers.

Authors:  Jarasvech Chinsangaram; Kady M Honeychurch; Shanthakumar R Tyavanagimatt; Janet M Leeds; Tove' C Bolken; Kevin F Jones; Robert Jordan; Thomas Marbury; Jon Ruckle; Denis Mee-Lee; Eric Ross; Israel Lichtenstein; Margaret Pickens; Michael Corrado; Jean M Clarke; Annie M Frimm; Dennis E Hruby
Journal:  Antimicrob Agents Chemother       Date:  2012-07-09       Impact factor: 5.938

6.  Historical perspectives in the development of antiviral agents against poxviruses.

Authors:  Erik De Clercq
Journal:  Viruses       Date:  2010-06-14       Impact factor: 5.818

7.  Development of ST-246® for Treatment of Poxvirus Infections.

Authors:  Robert Jordan; Janet M Leeds; Shanthakumar Tyavanagimatt; Dennis E Hruby
Journal:  Viruses       Date:  2010-11-03       Impact factor: 5.818

8.  Comparison of the safety and pharmacokinetics of ST-246® after i.v. infusion or oral administration in mice, rabbits and monkeys.

Authors:  Yali Chen; Adams Amantana; Shanthakumar R Tyavanagimatt; Daniela Zima; X Steven Yan; Gopi Kasi; Morgan Weeks; Melialani A Stone; William C Weimers; Peter Samuel; Ying Tan; Kevin F Jones; Daniel R Lee; Shirley S Kickner; Bradley M Saville; Martin Lauzon; Alan McIntyre; Kady M Honeychurch; Robert Jordan; Dennis E Hruby; Janet M Leeds
Journal:  PLoS One       Date:  2011-08-15       Impact factor: 3.752

9.  Polycyclic N-benzamido imides with potent activity against vaccinia virus.

Authors:  Eva Torres; María D Duque; Pelayo Camps; Lieve Naesens; Teresa Calvet; Mercè Font-Bardia; Santiago Vázquez
Journal:  ChemMedChem       Date:  2010-12-03       Impact factor: 3.540

10.  Single-dose safety and pharmacokinetics of ST-246, a novel orthopoxvirus egress inhibitor.

Authors:  Robert Jordan; Deborah Tien; Tove' C Bolken; Kevin F Jones; Shanthakumar R Tyavanagimatt; Josef Strasser; Annie Frimm; Michael L Corrado; Phoebe G Strome; Dennis E Hruby
Journal:  Antimicrob Agents Chemother       Date:  2008-03-03       Impact factor: 5.938
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