Literature DB >> 21300861

Synthetic ozonide drug candidate OZ439 offers new hope for a single-dose cure of uncomplicated malaria.

Susan A Charman1, Sarah Arbe-Barnes, Ian C Bathurst, Reto Brun, Michael Campbell, William N Charman, Francis C K Chiu, Jacques Chollet, J Carl Craft, Darren J Creek, Yuxiang Dong, Hugues Matile, Melanie Maurer, Julia Morizzi, Tien Nguyen, Petros Papastogiannidis, Christian Scheurer, David M Shackleford, Kamaraj Sriraghavan, Lukas Stingelin, Yuanqing Tang, Heinrich Urwyler, Xiaofang Wang, Karen L White, Sergio Wittlin, Lin Zhou, Jonathan L Vennerstrom.   

Abstract

Ozonide OZ439 is a synthetic peroxide antimalarial drug candidate designed to provide a single-dose oral cure in humans. OZ439 has successfully completed Phase I clinical trials, where it was shown to be safe at doses up to 1,600 mg and is currently undergoing Phase IIa trials in malaria patients. Herein, we describe the discovery of OZ439 and the exceptional antimalarial and pharmacokinetic properties that led to its selection as a clinical drug development candidate. In vitro, OZ439 is fast-acting against all asexual erythrocytic Plasmodium falciparum stages with IC(50) values comparable to those for the clinically used artemisinin derivatives. Unlike all other synthetic peroxides and semisynthetic artemisinin derivatives, OZ439 completely cures Plasmodium berghei-infected mice with a single oral dose of 20 mg/kg and exhibits prophylactic activity superior to that of the benchmark chemoprophylactic agent, mefloquine. Compared with other peroxide-containing antimalarial agents, such as the artemisinin derivatives and the first-generation ozonide OZ277, OZ439 exhibits a substantial increase in the pharmacokinetic half-life and blood concentration versus time profile in three preclinical species. The outstanding efficacy and prolonged blood concentrations of OZ439 are the result of a design strategy that stabilizes the intrinsically unstable pharmacophoric peroxide bond, thereby reducing clearance yet maintaining the necessary Fe(II)-reactivity to elicit parasite death.

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Year:  2011        PMID: 21300861      PMCID: PMC3060245          DOI: 10.1073/pnas.1015762108

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  35 in total

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Authors:  Paul M O'Neill; Gary H Posner
Journal:  J Med Chem       Date:  2004-06-03       Impact factor: 7.446

2.  The antimalarial drug artemisinin alkylates heme in infected mice.

Authors:  Anne Robert; Françoise Benoit-Vical; Catherine Claparols; Bernard Meunier
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-09       Impact factor: 11.205

3.  Malaria. Did they really say ... eradication?

Authors:  Leslie Roberts; Martin Enserink
Journal:  Science       Date:  2007-12-07       Impact factor: 47.728

4.  Arterolane, a new synthetic trioxolane for treatment of uncomplicated Plasmodium falciparum malaria: a phase II, multicenter, randomized, dose-finding clinical trial.

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Journal:  Clin Infect Dis       Date:  2010-09-15       Impact factor: 9.079

Review 5.  Artemisinin: mechanisms of action, resistance and toxicity.

Authors:  Steven R Meshnick
Journal:  Int J Parasitol       Date:  2002-12-04       Impact factor: 3.981

Review 6.  Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action.

Authors:  C W Jefford
Journal:  Curr Med Chem       Date:  2001-12       Impact factor: 4.530

7.  Spiro and dispiro-1,2,4-trioxolanes as antimalarial peroxides: charting a workable structure-activity relationship using simple prototypes.

Authors:  Yuxiang Dong; Jacques Chollet; Hugues Matile; Susan A Charman; Francis C K Chiu; William N Charman; Bernard Scorneaux; Heinrich Urwyler; Josefina Santo Tomas; Christian Scheurer; Christopher Snyder; Arnulf Dorn; Xiaofang Wang; Jean M Karle; Yuanqing Tang; Sergio Wittlin; Reto Brun; Jonathan L Vennerstrom
Journal:  J Med Chem       Date:  2005-07-28       Impact factor: 7.446

8.  In vitro assessment of the pharmacodynamic properties of DB75, piperaquine, OZ277 and OZ401 in cultures of Plasmodium falciparum.

Authors:  Sandra Hofer; Reto Brun; Sonja Maerki; Hugues Matile; Christian Scheurer; Sergio Wittlin
Journal:  J Antimicrob Chemother       Date:  2008-07-30       Impact factor: 5.790

9.  Identification of an antimalarial synthetic trioxolane drug development candidate.

Authors:  Jonathan L Vennerstrom; Sarah Arbe-Barnes; Reto Brun; Susan A Charman; Francis C K Chiu; Jacques Chollet; Yuxiang Dong; Arnulf Dorn; Daniel Hunziker; Hugues Matile; Kylie McIntosh; Maniyan Padmanilayam; Josefina Santo Tomas; Christian Scheurer; Bernard Scorneaux; Yuanqing Tang; Heinrich Urwyler; Sergio Wittlin; William N Charman
Journal:  Nature       Date:  2004-08-19       Impact factor: 49.962

10.  Ensuring sustained ACT production and reliable artemisinin supply.

Authors:  Jean-Marie Kindermans; Jacques Pilloy; Piero Olliaro; Melba Gomes
Journal:  Malar J       Date:  2007-09-15       Impact factor: 2.979

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  136 in total

Review 1.  Antimalarial drug resistance: linking Plasmodium falciparum parasite biology to the clinic.

Authors:  Benjamin Blasco; Didier Leroy; David A Fidock
Journal:  Nat Med       Date:  2017-08-04       Impact factor: 53.440

2.  Malaria-infected mice are completely cured by one 6 mg/kg oral dose of a new monomeric trioxane sulfide combined with mefloquine.

Authors:  Rachel D Slack; Bryan T Mott; Lauren E Woodard; Abhai Tripathi; Abhai Triphati; David Sullivan; Elizabeth Nenortas; Sonya C T Girdwood; Theresa A Shapiro; Gary H Posner
Journal:  J Med Chem       Date:  2011-12-15       Impact factor: 7.446

3.  Malarial dihydrofolate reductase as a paradigm for drug development against a resistance-compromised target.

Authors:  Yongyuth Yuthavong; Bongkoch Tarnchompoo; Tirayut Vilaivan; Penchit Chitnumsub; Sumalee Kamchonwongpaisan; Susan A Charman; Danielle N McLennan; Karen L White; Livia Vivas; Emily Bongard; Chawanee Thongphanchang; Supannee Taweechai; Jarunee Vanichtanankul; Roonglawan Rattanajak; Uthai Arwon; Pascal Fantauzzi; Jirundon Yuvaniyama; William N Charman; David Matthews
Journal:  Proc Natl Acad Sci U S A       Date:  2012-10-03       Impact factor: 11.205

Review 4.  Malaria biology and disease pathogenesis: insights for new treatments.

Authors:  Louis H Miller; Hans C Ackerman; Xin-zhuan Su; Thomas E Wellems
Journal:  Nat Med       Date:  2013-02-06       Impact factor: 53.440

5.  Pharmacokinetics of the Antischistosomal Lead Ozonide OZ418 in Uninfected Mice Determined by Liquid Chromatography-Tandem Mass Spectrometry.

Authors:  Anna Leonidova; Mireille Vargas; Jörg Huwyler; Jennifer Keiser
Journal:  Antimicrob Agents Chemother       Date:  2016-11-21       Impact factor: 5.191

6.  Inhibition of cytochrome bc1 as a strategy for single-dose, multi-stage antimalarial therapy.

Authors:  Allison M Stickles; Li-Min Ting; Joanne M Morrisey; Yuexin Li; Michael W Mather; Erin Meermeier; April M Pershing; Isaac P Forquer; Galen P Miley; Sovitj Pou; Rolf W Winter; David J Hinrichs; Jane X Kelly; Kami Kim; Akhil B Vaidya; Michael K Riscoe; Aaron Nilsen
Journal:  Am J Trop Med Hyg       Date:  2015-04-27       Impact factor: 2.345

7.  Antimalarial chemotherapy: orally curative artemisinin-derived trioxane dimer esters.

Authors:  Ryan C Conyers; Jennifer R Mazzone; Abhai K Tripathi; David J Sullivan; Gary H Posner
Journal:  Bioorg Med Chem Lett       Date:  2014-11-27       Impact factor: 2.823

8.  Metabolomic Profiling of the Malaria Box Reveals Antimalarial Target Pathways.

Authors:  Erik L Allman; Heather J Painter; Jasmeet Samra; Manuela Carrasquilla; Manuel Llinás
Journal:  Antimicrob Agents Chemother       Date:  2016-10-21       Impact factor: 5.191

Review 9.  Antimalarial drug discovery - approaches and progress towards new medicines.

Authors:  Erika L Flannery; Arnab K Chatterjee; Elizabeth A Winzeler
Journal:  Nat Rev Microbiol       Date:  2013-11-11       Impact factor: 60.633

10.  Lead Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series for the Treatment of Malaria.

Authors:  Sreekanth Kokkonda; Xiaoyi Deng; Karen L White; Farah El Mazouni; John White; David M Shackleford; Kasiram Katneni; Francis C K Chiu; Helena Barker; Jenna McLaren; Elly Crighton; Gong Chen; Inigo Angulo-Barturen; Maria Belen Jimenez-Diaz; Santiago Ferrer; Leticia Huertas-Valentin; Maria Santos Martinez-Martinez; Maria Jose Lafuente-Monasterio; Rajesh Chittimalla; Shatrughan P Shahi; Sergio Wittlin; David Waterson; Jeremy N Burrows; Dave Matthews; Diana Tomchick; Pradipsinh K Rathod; Michael J Palmer; Susan A Charman; Margaret A Phillips
Journal:  J Med Chem       Date:  2020-04-16       Impact factor: 7.446

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