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Xenobiotica
the fate of foreign compounds in biological systems
Volume 35, 2005 - Issue 3
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Research Article

In vitro metabolism of an orally active O-methyl amidoxime prodrug for the treatment of CNS trypanosomiasis

J. H Ansede Division of Drug Delivery and Disposition, School of Pharmacy, The University of North Carolina at Chapel Hill, Chapel Hill, USA
,
R. D Voyksner LCMS Ltd, Durham, USA
,
M. A Ismail Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, USA
,
D. W Boykin Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, USA
,
R. R Tidwell Department of Pathology, School of Medicine, The University of North Carolina at Chapel Hill, Chapel Hill, USA
&
J. E Hall Division of Drug Delivery and Disposition, School of Pharmacy, The University of North Carolina at Chapel Hill, Chapel Hill, USA; Department of Pathology, School of Medicine, The University of North Carolina at Chapel Hill, Chapel Hill, USACorrespondence[email protected]
Pages 211-226 | Received 04 Nov 2004, Published online: 22 Sep 2008

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Antje Havemeyer, Juliane Lang & Bernd Clement. (2011) The fourth mammalian molybdenum enzyme mARC: current state of research. Drug Metabolism Reviews 43:4, pages 524-539.
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Conor R Caffrey & Dietmar Steverding. (2008) Recent initiatives and strategies to developing new drugs for tropical parasitic diseases. Expert Opinion on Drug Discovery 3:2, pages 173-186.
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Articles from other publishers (27)

Yu Zhao, Li Li, Zitong Zhou, Man Chen, Weiguang Yang & Hui Luo. (2021) Copper catalyzed five-component domino strategy for the synthesis of nicotinimidamides. Organic & Biomolecular Chemistry 19:17, pages 3868-3872.
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Montaser Sh. Shaykoon, Adel A. Marzouk, Osama M. Soltan, Amira S. Wanas, Mohamed M. Radwan, Ahmed M. Gouda, Bahaa G.M. Youssif & Mohamed Abdel-Aziz. (2020) Design, synthesis and antitrypanosomal activity of heteroaryl-based 1,2,4-triazole and 1,3,4-oxadiazole derivatives. Bioorganic Chemistry 100, pages 103933.
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Emily A. Dickie, Federica Giordani, Matthew K. Gould, Pascal Mäser, Christian Burri, Jeremy C. Mottram, Srinivasa P. S. Rao & Michael P. Barrett. (2020) New Drugs for Human African Trypanosomiasis: A Twenty First Century Success Story. Tropical Medicine and Infectious Disease 5:1, pages 29.
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Mohamed A. Ismail, Wael M. El-Sayed, Saad Shaaban, Ghada A. Abdelwahab & Wafaa S. Hamama. (2020) A Review of Cationic Arylfurans and Their Isosteres: Synthesis and Biological Importance. Current Organic Chemistry 23:24, pages 2751-2782.
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Michael Berninger, Ines Schmidt, Alicia Ponte-Sucre & Ulrike Holzgrabe. (2017) Novel lead compounds in pre-clinical development against African sleeping sickness. MedChemComm 8:10, pages 1872-1890.
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Gudrun Ott, Antje Havemeyer & Bernd Clement. (2014) The mammalian molybdenum enzymes of mARC. JBIC Journal of Biological Inorganic Chemistry 20:2, pages 265-275.
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John K. Thuita, Kristina K. Wolf, Grace A. Murilla, Arlene S. Bridges, David W. Boykin, James N. Mutuku, Qiang Liu, Susan K. Jones, Charles O. Gem, Shelley Ching, Richard R. Tidwell, Michael Z. Wang, Mary F. Paine & Reto Brun. (2015) Chemotherapy of Second Stage Human African Trypanosomiasis: Comparison between the Parenteral Diamidine DB829 and Its Oral Prodrug DB868 in Vervet Monkeys. PLOS Neglected Tropical Diseases 9:2, pages e0003409.
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Wujian Ju, Sihyung Yang, John H. Ansede, Chad E. Stephens, Arlene S. Bridges, Robert D. Voyksner, Mohamed A. Ismail, David W. Boykin, Richard R. Tidwell, James Edwin Hall & Michael Zhuo Wang. (2014) CYP1A1 and CYP1B1-Mediated Biotransformation of the Antitrypanosomal Methamidoxime Prodrug DB844 Forms Novel Metabolites Through Intramolecular Rearrangement. Journal of Pharmaceutical Sciences 103:1, pages 337-349.
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Laixing Hu, Alpa Patel, Lavanya Bondada, Sihyung Yang, Michael Zhuo Wang, Manoj Munde, W. David Wilson, Tanja Wenzler, Reto Brun & David W. Boykin. (2013) Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues. Bioorganic & Medicinal Chemistry 21:21, pages 6732-6741.
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M. N. C. SOEIRO, K. WERBOVETZ, D. W. BOYKIN, W. D. WILSON, M. Z. WANG & A. HEMPHILL. (2013) Novel amidines and analogues as promising agents against intracellular parasites: a systematic review. Parasitology 140:8, pages 929-951.
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John K. Thuita, Kristina K. Wolf, Grace A. Murilla, Qiang Liu, James N. Mutuku, Yao Chen, Arlene S. Bridges, Raymond E. Mdachi, Mohamed A. Ismail, Shelley Ching, David W. Boykin, James Edwin Hall, Richard R. Tidwell, Mary F. Paine, Reto Brun & Michael Zhuo Wang. (2013) Safety, Pharmacokinetic, and Efficacy Studies of Oral DB868 in a First Stage Vervet Monkey Model of Human African Trypanosomiasis. PLoS Neglected Tropical Diseases 7:6, pages e2230.
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Cyrus J. Bacchi, Robert T. Jacobs & Nigel Yarlett. 2013. Trypanosomatid Diseases. Trypanosomatid Diseases 515 529 .
Claudia N. Generaux, Garrett R. Ainslie, Arlene S. Bridges, Mohamed A. Ismail, David W. Boykin, Richard R. Tidwell, Dhiren R. Thakker & Mary F. Paine. (2013) Compartmental and Enzyme Kinetic Modeling To Elucidate the Biotransformation Pathway of a Centrally Acting Antitrypanosomal Prodrug. Drug Metabolism and Disposition 41:2, pages 518-528.
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John K. Thuita, Michael Z. Wang, John M. Kagira, Cathrine L. Denton, Mary F. Paine, Raymond E. Mdachi, Grace A. Murilla, Shelley Ching, David W. Boykin, Richard R. Tidwell, James E. Hall & Reto Brun. (2012) Pharmacology of DB844, an Orally Active aza Analogue of Pafuramidine, in a Monkey Model of Second Stage Human African Trypanosomiasis. PLoS Neglected Tropical Diseases 6:7, pages e1734.
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Jiajiu Shaw, Brian Shay, Jack Jiang, Frederick Valeriote & Ben Chen. (2011) Metabolism studies of a small-molecule tumor necrosis factor-alpha (TNF-α) inhibitor, UTL-5b (GBL-5b). European Journal of Drug Metabolism and Pharmacokinetics 37:2, pages 83-89.
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Xuanmao Chen, Beverley A. Orser & John F. MacDonald. (2010) Design and screening of ASIC inhibitors based on aromatic diamidines for combating neurological disorders. European Journal of Pharmacology 648:1-3, pages 15-23.
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Danuta Branowska, Abdelbasset A. Farahat, Arvind Kumar, Tanja Wenzler, Reto Brun, Yang Liu, W. David Wilson & David W. Boykin. (2010) Synthesis and antiprotozoal activity of 2,5-bis[amidinoaryl]thiazoles. Bioorganic & Medicinal Chemistry 18:10, pages 3551-3558.
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Dennis Schade, Joscha Kotthaus, Helen Hungeling, Jürke Kotthaus & Bernd Clement. (2009) The Peptidylglycine α-Amidating Monooxygenase (PAM): A Novel Prodrug Strategy for Amidoximes and N -Hydroxyguanidines? . ChemMedChem 4:10, pages 1595-1599.
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Tanja Wenzler, David W. Boykin, Mohamed A. Ismail, James Edwin Hall, Richard R. Tidwell & Reto Brun. (2009) New Treatment Option for Second-Stage African Sleeping Sickness: In Vitro and In Vivo Efficacy of Aza Analogs of DB289. Antimicrobial Agents and Chemotherapy 53:10, pages 4185-4192.
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Shane R. Wilkinson & John M. Kelly. (2009) Trypanocidal drugs: mechanisms, resistance and new targets. Expert Reviews in Molecular Medicine 11.
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Laixing Hu, Reem K. Arafa, Mohamed A. Ismail, Alpa Patel, Manoj Munde, W. David Wilson, Tanja Wenzler, Reto Brun & David W. Boykin. (2009) Synthesis and activity of azaterphenyl diamidines against Trypanosoma brucei rhodesiense and Plasmodium falciparum. Bioorganic & Medicinal Chemistry 17:18, pages 6651-6658.
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Bernard Testa & Stefanie D. Krämer. (2009) The Biochemistry of Drug Metabolism – An Introduction. Chemistry & Biodiversity 6:5, pages 591-684.
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W. David Wilson, Farial A. Tanious, Amanda Mathis, Denise Tevis, James Edwin Hall & David W. Boykin. (2008) Antiparasitic compounds that target DNA. Biochimie 90:7, pages 999-1014.
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Mohamed A. Ismail, Reem K. Arafa, Tanja Wenzler, Reto Brun, Farial A. Tanious, W. David Wilson & David W. Boykin. (2008) Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines. Bioorganic & Medicinal Chemistry 16:2, pages 683-691.
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M P Barrett, D W Boykin, R Brun & R R Tidwell. (2007) Human African trypanosomiasis: pharmacological re-engagement with a neglected disease. British Journal of Pharmacology 152:8, pages 1155-1171.
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Mohamed A. Ismail & David W. Boykin. (2006) Synthesis of deuterium and15N-labelled 2,5-Bis[5-amidino-2-pyridyl]furan and 2,5-Bis[5-(methoxyamidino)-2-pyridyl]furan. Journal of Labelled Compounds and Radiopharmaceuticals 49:11, pages 985-996.
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Michael P. Barrett & Ian H. Gilbert. 2006. Advances in Parasitology Volume 63. Advances in Parasitology Volume 63 125 183 .

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