Absorption, distribution, metabolism, and excretion of the novel antibacterial prodrug tedizolid phosphate

Drug Metabolism and Disposition

Volumn 42, Issue 8, 2014, Pages 1275-1284

  Ong, Voon ^a   Flanagan, Shawn ^a   Fang, Edward ^a   Dreskin, Howard J ^a   Locke, Jeffrey B ^a   Bartizal, Kenneth ^a   Prokocimer, Philippe ^a  

^a Cubist Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LINEZOLID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TEDIZOLID; ANTIINFECTIVE AGENT; ORGANOPHOSPHATE; OXAZOLE DERIVATIVE; PRODRUG;

ANTIBACTERIAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BLOOD SAMPLING; CONTROLLED STUDY; DECARBOXYLATION; DISTRIBUTION VOLUME; DOG; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG DOSE COMPARISON; DRUG ELIMINATION; DRUG EXCRETION; DRUG GLUCURONIDATION; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG METABOLISM; DRUG OXIDATION; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG SULFATION; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ENTEROCOCCUS FAECIUM; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; LIVER METABOLISM; MALE; MAXIMUM PLASMA CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; RADIOACTIVITY; RAT; SINGLE DRUG DOSE; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES; TIME TO MAXIMUM PLASMA CONCENTRATION; TISSUE DISTRIBUTION; ADOLESCENT; ADULT; ANIMAL; CLINICAL TRIAL; HALF LIFE TIME; INTRAVENOUS DRUG ADMINISTRATION; KINETICS; LIVER MICROSOME; METABOLISM; MIDDLE AGED; ORAL DRUG ADMINISTRATION; PHASE 1 CLINICAL TRIAL; PHYSIOLOGY; SPRAGUE DAWLEY RAT; YOUNG ADULT;

ADMINISTRATION, INTRAVENOUS; ADMINISTRATION, ORAL; ADOLESCENT; ADULT; ANIMALS; ANTI-BACTERIAL AGENTS; DOGS; FEMALE; HALF-LIFE; HUMANS; KINETICS; MALE; MICROSOMES, LIVER; MIDDLE AGED; ORGANOPHOSPHATES; OXAZOLES; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; TISSUE DISTRIBUTION; YOUNG ADULT;

EID: 84904216511     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.056697     Document Type: Article

References (36)

1. Baker CN and Tenover FC (1996) Evaluation of Alamar colorimetric broth microdilution susceptibility testing method for staphylococci and enterococci. J Clin Microbiol 34:2654-2659. (Pubitemid 26346480)
2. Bhamidipati RK, Dravid PV, Mullangi R, and Srinivas NR (2004) Prediction of clinical pharmacokinetic parameters of linezolid using animal data by allometric scaling: applicability for the development of novel oxazolidinones. Xenobiotica 34:571-579. (Pubitemid 38981370)
3. Carlini EJ, Raftogianis RB, Wood TC, Jin F, Zheng W, Rebbeck TR, and Weinshilboum RM (2001) Sulfation pharmacogenetics: SULT1A1 and SULT1A2 allele frequencies in Caucasian, Chinese and African-American subjects. Pharmacogenetics 11:57-68. (Pubitemid 32108662)
4. Chan L, Diep B, Basuino L, and Chambers H (2009) Comparative efficacy of TR-701 (prodrug of torezolid), vancomycin (vanco) and daptomycin (dapto) in a rabbit model of methicillin-resistant Staphylococcus aureus (MRSA) endocarditis. Poster B-050. 49th Annual Meeting of the Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC); 2009 Sep 12-15; San Francisco, CA. American Society for Microbiology, Washington, DC.
5. Clinical and Laboratory Standards Institute (CLSI) (2012) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard - 9th ed. CLSI document M7-A9. Clinical and Laboratory Standards Institute, Wayne, PA. http://antimicrobianos.com.ar/ATB/wp-content/ uploads/2012/11/03-CLSI-M07-A9-2012.pdf. Accessed March 19, 2014.
6. Das D, Lambert A, Tulkens PM, Muccioli GG, and Van Bambeke F (2012) Study of the cellular uptake and subcellular distribution of the oxazolidinone tedizolid (TZD) in murine J774 macrophages: lack of association with mitochondria. Poster A-1291. 52nd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC); 2012 Sep 9-12; San Francisco, CA. American Society for Microbiology, Washington, DC.
7. Fang E, De Anda C, Das A, and Prokocimer P (2013) Efficacy and safety results from the ESTABLISH-2 ABSSSI study comparing intravenous and oral tedizolid phosphate and linezolid. Poster LB2964. 23rd European Congress of Clinical Microbiology and Infectious Diseases (ECCMID); 2013 Apr 27-30; Berlin, Germany. European Society of Clinical Microbiology and Infectious Diseases, Basel, Switzerland.
8. Flanagan S, Bartizal K, Minassian SL, Fang E, and Prokocimer P (2013) In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. Antimicrob Agents Chemother 57:3060-3066.
9. Flanagan S, Boyea T, Dreskin H, Minassian S, Marbury T, Alcorn H, Fang E, and Prokocimer P (2012a) A phase 1 study of orally administered tedizolid phosphate in subjects with moderate or severe hepatic impairment. Poster A-1295. 52nd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC); 2012 Sep 9-12; San Francisco, CA. American Society for Microbiology, Washington, DC.
10. Flanagan S, Morris D, Boyea T, Dreskin H, Minassian S, Alcorn H, Marbury T, Abdelhameed M, Fang E, and Prokocimer P (2012b) A phase 1 study of intravenously administered tedizolid phosphate in subjects with advanced renal impairment. Poster A-1294. 52nd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC); 2012 Sep 9-12; San Francisco, CA. American Society for Microbiology, Washington, DC.
11. Gamage N, Barnett A, Hempel N, Duggleby RG, Windmill KF, Martin JL, and McManus ME (2006) Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5-22. (Pubitemid 43264722)
12. Hebbring SJ, Moyer AM, and Weinshilboum RM (2008) Sulfotransferase gene copy number variation: pharmacogenetics and function. Cytogenet Genome Res 123:205-210.
13. Hildebrandt MA, Carrington DP, Thomae BA, Eckloff BW, Schaid DJ, Yee VC, Weinshilboum RM, and Wieben ED (2007) Genetic diversity and function in the human cytosolic sulfotransferases. Pharmacogenomics J 7:133-143. (Pubitemid 46577846)
14. Hop CE, Wang Z, Chen Q, and Kwei G (1998) Plasma-pooling methods to increase throughput for in vivo pharmacokinetic screening. J Pharm Sci 87:901-903. (Pubitemid 28319423)
15. Jakoby WB and Ziegler DM (1990) The enzymes of detoxication. J Biol Chem 265:20715-20718. (Pubitemid 120014066)
16. Jia L and Liu X (2007) The conduct of drug metabolism studies considered good practice (II): in vitro experiments. Curr Drug Metab 8:822-829. (Pubitemid 350238912)
17. Kanafani ZA and Corey GR (2012) Tedizolid (TR-701): a new oxazolidinone with enhanced potency. Expert Opin Investig Drugs 21:515-522.
18. Lang D, Freudenberger C, and Weinz C (2009) In vitro metabolism of rivaroxaban, an oral, direct factor Xa inhibitor, in liver microsomes and hepatocytes of rats, dogs, and humans. Drug Metab Dispos 37:1046-1055.
19. Leach KL, Brickner SJ, Noe MC, and Miller PF (2011) Linezolid, the first oxazolidinone antibacterial agent. Ann N Y Acad Sci 1222:49-54.
20. Lepak AJ, Marchillo K, Pichereau S, Craig WA, and Andes DR (2012) Comparative pharmacodynamics of the new oxazolidinone tedizolid phosphate and linezolid in a neutropenic murine Staphylococcus aureus pneumonia model. Antimicrob Agents Chemother 56:5916-5922.
21. Lindsay J, Wang LL, Li Y, and Zhou SF (2008) Structure, function and polymorphism of human cytosolic sulfotransferases. Curr Drug Metab 9:99-105. (Pubitemid 351460999)
22. Locke JB, Zurenko GE, Shaw KJ, and Bartizal K (2014) Tedizolid for the management of human infections: in vitro characteristics. Clin Infect Dis 58 (Suppl 1):S35-S42.
23. Louie A, Liu W, Kulawy R, and Drusano GL (2011) In vivo pharmacodynamics of torezolid phosphate (TR-701), a new oxazolidinone antibiotic, against methicillin-susceptible and methicillin-resistant Staphylococcus aureus strains in a mouse thigh infection model. Antimicrob Agents Chemother 55:3453-3460.
24. Nagar S, Walther S, and Blanchard RL (2006) Sulfotransferase (SULT) 1A1 polymorphic variants*1,*2, and*3 are associated with altered enzymatic activity, cellular phenotype, and protein degradation. Mol Pharmacol 69:2084-2092. (Pubitemid 43894328)
25. Plock N, Buerger C, Joukhadar C, Kljucar S, and Kloft C (2007) Does linezolid inhibit its own metabolism? Population pharmacokinetics as a tool to explain the observed nonlinearity in both healthy volunteers and septic patients. Drug Metab Dispos 35:1816-1823. (Pubitemid 47481573)
26. Prokocimer P, Bien P, Surber J, Mehra P, DeAnda C, Bulitta JB, and Corey GR (2011) Phase 2, randomized, double-blind, dose-ranging study evaluating the safety, tolerability, population pharmacokinetics, and efficacy of oral torezolid phosphate in patients with complicated skin and skin structure infections. Antimicrob Agents Chemother 55:583-592.
27. Prokocimer P, De Anda C, Fang E, Mehra P, and Das A (2013) Tedizolid phosphate vs linezolid for treatment of acute bacterial skin and skin structure infections: the ESTABLISH-1 randomized trial. JAMA 309:559-569.
28. Shaw KJ and Barbachyn MR (2011) The oxazolidinones: past, present, and future. Ann N Y Acad Sci 1241:48-70.
29. Slatter JG, Adams LA, Bush EC, Chiba K, Daley-Yates PT, Feenstra KL, Koike S, Ozawa N, Peng GW, and Sams JP, et al. (2002) Pharmacokinetics, toxicokinetics, distribution, metabolism and excretion of linezolid in mouse, rat and dog. Xenobiotica 32:907-924. (Pubitemid 35155524)
30. Slatter JG, Stalker DJ, Feenstra KL, Welshman IR, Bruss JB, Sams JP, Johnson MG, Sanders PE, Hauer MJ, and Fagerness PE, et al. (2001) Pharmacokinetics, metabolism, and excretion of linezolid following an oral dose of [(14)C]linezolid to healthy human subjects. Drug Metab Dispos 29:1136-1145. (Pubitemid 32660533)
31. Stalker DJ and Jungbluth GL (2003) Clinical pharmacokinetics of linezolid, a novel oxazolidinone antibacterial. Clin Pharmacokinet 42:1129-1140. (Pubitemid 37357649)
32. Takahashi Y, Takesue Y, Nakajima K, Ichiki K, Tsuchida T, Tatsumi S, Ishihara M, Ikeuchi H, and Uchino M (2011) Risk factors associated with the development of thrombocytopenia in patients who received linezolid therapy. J Infect Chemother 17:382-387.
33. Tang L, Zhou J, Yang CH, Xia BJ, Hu M, and Liu ZQ (2012) Systematic studies of sulfation and glucuronidation of 12 flavonoids in the mouse liver S9 fraction reveal both unique and shared positional preferences. J Agric Food Chem 60:3223-3233.
34. Weinz C, Schwarz T, Kubitza D, Mueck W, and Lang D (2009) Metabolism and excretion of rivaroxaban, an oral, direct factor Xa inhibitor, in rats, dogs, and humans. Drug Metab Dispos 37:1056-1064.
35. Wu B, Basu S, Meng S, Wang X, and Hu M (2011) Regioselective sulfation and glucuronidation of phenolics: insights into the structural basis. Curr Drug Metab 12:900-916.
36. Wynalda MA, Hauer MJ, and Wienkers LC (2000) Oxidation of the novel oxazolidinone antibiotic linezolid in human liver microsomes. Drug Metab Dispos 28:1014-1017. (Pubitemid 30660353)