Analysis of macrolide antibiotics, using liquid chromatography-mass spectrometry, in food, biological and environmental matrices

Mass Spectrometry Reviews

Volumn 28, Issue 1, 2009, Pages 50-92

  Wang, Jian ^a  

^a CANADIAN FOOD INSPECTION AGENCY   (Canada)

Author keywords

Environment; Food safety; Liquid chromatography; Liquid liquid extraction; Macrolides; Mass spectrometry; Pharmacokinetics; Solid phase extraction; Ultra performance liquid chromatography

Indexed keywords

ANTIBIOTICS; BODY FLUIDS; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; DEGRADATION; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; NEGATIVE IONS; PHARMACOKINETICS; PHOTODEGRADATION; QUANTUM OPTICS; SEWAGE TREATMENT PLANTS; SOLVENT EXTRACTION; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS; UNCERTAINTY ANALYSIS;

ENVIRONMENT; FOOD SAFETY; LIQUID-LIQUID EXTRACTION; MACROLIDES; SOLID-PHASE EXTRACTION; ULTRA-PERFORMANCE LIQUID CHROMATOGRAPHY;

LIQUID CHROMATOGRAPHY;

ANTIINFECTIVE AGENT; DRUG RESIDUE; MACROLIDE;

ANIMAL; ATMOSPHERIC PRESSURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ENVIRONMENTAL MONITORING; FOOD ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; METHODOLOGY; POLLUTANT; REVIEW;

ANIMALS; ANTI-BACTERIAL AGENTS; ATMOSPHERIC PRESSURE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG RESIDUES; ENVIRONMENTAL MONITORING; ENVIRONMENTAL POLLUTANTS; FOOD ANALYSIS; HUMANS; MACROLIDES; MASS SPECTROMETRY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 59149095760     PISSN: 02777037     EISSN: None     Source Type: Journal    
DOI: 10.1002/mas.20189     Document Type: Article

References (202)

1. Abuin S, Codony R, Compano R, Granados M, Prat MD. 2006. Analysis of macrolide antibiotics in river water by solid-phase extraction and liquid chromatography-mass spectrometry. J Chromatogr A 1114: 73-81.
2. Ballow CH, Amsden GW. 1992. Azithromycin: The first azalide antibiotic. Ann Pharmacother 26:1253-1261.
3. Barcelo D, Petrovic M. 2007. Challenges and achievements of LC-MS in environmental analysis: 25 years on. Trends Anal Chem 26:2-11.
4. Barrett B, Borek-Dohalsky V, Fejt P, Vaingatova S, Huclova J, Nemec B, Jelinek I. 2005. Validated HPLC-MS-MS method for determination of azithromycin in human plasma. Anal Bioanal Chem 383:210-217.
5. Barwick V, Ellison SLR. 1999. Measurement uncertainty: Approaches to the evaluation of uncertainties associated with recovery. Analyst 124:981-990.
6. Batt AL, Snow DD, Aga DS. 2006. Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA. Chemosphere 64:1963-1971.
7. Beausse J. 2004. Selected drugs in solid matrices: A review of environmental determination, occurrence and properties of principal substances. Trends Anal Chem 23:753-761.
8. Benchaoui HA, Nowakowski M, Sherington J, Rowan TG, Sunderland SJ. 2004. Pharmacokinetics and lung tissue concentrations of tulathromycin in swine. J Vet Pharmacol Ther 27:203-210.
9. Benetti C, Piro R, Binato G, Angeletti R, Biancotto G. 2006. Simultaneous determination of lincomycin and five macrolide antibiotic residues in honey by liquid chromatography coupled to electrospray ionization mass spectrometry (LC-MS/MS). Food Addit Contam 23:1099-1108.
10. Berrada H, Borrull F, Font G, Molto JC, Marce RM. 2007. Validation of a confirmatory method for the determination of macrolides in liver and kidney animal tissues in accordance with the European Union regulation 2002/657/EC. J Chromatogr A 1157:281-288.
11. Billedeau SM, Heinze TM, Siitonen PH. 2003. Liquid chromatography analysis of erythromycin A in salmon tissue by electrochemical detection with confirmation by electrospray ionization mass spectrometry. J Agric Food Chem 51:1534-1538.
12. Bogialli S, Di Corcia A, Lagana A, Mastrantoni V, Sergi M. 2007. A simple and rapid confirmatory assay for analyzing antibiotic residues of the macrolide class and lincomycin in bovine milk and yoghurt: Hot water extraction followed by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 21:237-246.
13. Bos SJ, van Leeuwen SM, Karst U. 2006. From fundamentals to applications: Recent developments in atmospheric pressure photoionization mass spectrometry. Anal Bioanal Chem 384:85-99.
14. Bryskier A. 1998. Roxithromycin: Review of its antimicrobial activity. J Antimicrob Chemother 41(Suppl B):1-21.
15. Bueno MJ, Aguera A, Gomez MJ, Hernando MD, Garcia-Reyes JF, Fernandez-Alba AR. 2007. Application of liquid chromatography/quadrupole-linear ion trap mass spectrometry and time-of-flight mass spectrometry to the determination of pharmaceuticals and related contaminants in wastewater. Anal Chem 79:9372-9384.
16. Bullock GL, Leek SL. 1986. Use of erythromycin in reducing vertical transmission of bacterial kidney disease. Vet Hum Toxicol 28(Suppl 1): 18-20.
17. CAHI. 2008. Canadian Animal Health Institute. http://www.cahi-icsa.ca/ food-resistance-macrolide.php.
18. Caldow M, Stead SL, Day J, Sharman M, Situ C, Elliott C. 2005. Development and validation of an optical SPR biosensor assay for tylosin residues in honey. J Agric Food Chem 53:7367-7370.
19. Carlson JC, Mabury SA. 2006. Dissipation kinetics and mobility of chlortetracycline, tylosin, and monensin in an agricultural soil in Northumberland County, Ontario, Canada. Environ Toxicol Chem 25:1-10.
20. Chamberlain E, Adams C. 2006. Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine. Water Res 40:2517-2526.
21. Chee-Sanford JC, Aminov RI, Krapac IJ, Garrigues-Jeanjean N, Mackie RI. 2001. Occurrence and diversity of tetracycline resistance genes in lagoons and groundwater underlying two swine production facilities. Appl. Environ Microbiol 67:1494-1502.
22. Chen BM, Liang YZ, Chen X, Liu SG, Deng FL, Zhou P. 2006. Quantitative determination of azithromycin in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study. J Pharm Biomed Anal 42:480-487.
23. Chen L, Qui F, Ma Y, Li F. 2007. Quantitative determination of azithromycin in human plasma by ultra performance liquid chromatography- electrospray ionization mass spectrometry and its application in a pharmacokinetic study. J Chromatogr B 855:255-261.
24. Cherlet M, De Baere S, Croubels S, De Backer P. 2002. Quantitation of tylosin in swine tissues by liquid chromatography combined with electrospray ionization mass spectrometry. Anal Chim Acta 473:167-175.
25. Chemushevich IV, Loboda AV, Thomson BA. 2001. An introduction to quadrupole-time-of-flight mass spectrometry. J Mass Spectrom 36: 849-865.
26. Chitneni SK, Govaerts C, Adams E, Van Schepdael A, Hoogmartens J. 2004. Identification of impurities in erythromycin by liquid chromatography-mass spectrometry detection. J Chromatogr A 1056:111-120.
27. Churchwell MI, Twaddle NC, Meeker LR, Doerge DR. 2005. Improving LC-MS sensitivity through increases in chromatographic performance: Comparisons of UPLC-ES/MS/MS to HPLC-ES/MS/MS. J Chromatogr B 825:134-143.
28. Codony R, Compano R, Granados M, Garcia-Regueiro JA, Prat MD. 2002. Residue analysis of macrolides in poultry muscle by liquid chromatography- electrospray mass spectrometry. J Chromatogr A 959:131-141.
29. Cotta MA, Whitehead TR, Zeltwanger RL. 2003. Isolation, characterization and comparison of bacteria from swine faeces and manure storage pits. Environ Microbiol 5:737-745.
30. Debremaeker D, Visky D, Chepkwony HK, Van Schepdael A, Roets E, Hoogmartens J. 2003. Analysis of unknown compounds in azithromycin bulk samples with liquid chromatography coupled to ion trap mass spectrometry. Rapid Commun Mass Spectrom 17:342-350.
31. Dehouck P, Van Looy E, Haghedooren E, Deckers K, Vander Heyden Y, Adams E, Roets E, Hoogmartens J. 2003a. Analysis of erythromycin and benzoylperoxide in topical gels by liquid chromatography. J Chromatogr B 794:293-302.
32. Dehouck P, Vander Heyden Y, Smeyers Verbeke J, Massart DL, Crommen J, Hubert P, Marini RD, Smeets OSNM, Decristoforo G, Van de Wauw W, De Beer J, Quaglia MG, Stella C, Veuthey JL, Estevenon O, Van Schepdael A, Roets E, Hoogmartens J. 2003b. Determination of uncertainty in analytical measurements from collaborative study results on the analysis of a phenoxymethylpenicillin sample. Anal Chim Acta 481:261-272.
33. Dehouck P, Vander Heyden Y, Smeyers Verbeke J, Massart DL, Marini RD, Chiap P, Hubert P, Crommen J, Van de Wauw W, De Beer J, Cox R, Mathieu G, Reepmeyer JC, Voigt B, Estevenon O, Nicolas A, Van Schepdael A, Adams E, Hoogmartens J. 2003c. Interlaboratory study of a liquid chromatography method for erythromycin: Determination of uncertainty. J Chromatogr A 1010:63-74.
34. Deubel A, Fandino AS, Sorgel F, Holzgrabe U. 2006. Determination of erythromycin and related substances in commercial samples using liquid chromatography/ion trap mass spectrometry. J Chromatogr A 1136:39-47.
35. Diana J, Govaerts C, Hoogmartens J, Van Schepdael A, Adams E. 2006. Characterization of impurities in dirithromycin by liquid chromatography/ion trap mass spectrometry. J Chromatogr A 1125:52-66.
36. Diaz-Cruz MS, Barcelo D. 2006. Determination of antimicrobial residues and metabolites in the aquatic environment by liquid chromatography tandem mass spectrometry. Anal Bioanal Chem 386:973-985.
37. Draisci R, delli Quadri F, Achene L, Volpe G, Palleschi L, Palleschi G. 2001a. A new electrochemical enzyme-linked immunosorbent assay for the screening of macrolide antibiotic residues in bovine meat. Analyst 126:1942-1946.
38. Draisci R, Palleschi L, Ferretti E, Achene L, Cecilia A. 2001b. Confirmatory method for macrolide residues in bovine tissues by micro-liquid chromatography-tandem mass spectrometry. J Chromatogr A 926:97-104.
39. Dubois M, Fluchard D, Sior E, Delahaut P. 2001. Identification and quantification of five macrolide antibiotics in several tissues, eggs and milk by liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr B 753:189-202.
40. 2377/90/EC. .1990. Council Regulation (EEC) No 2377/90 of 26 June 1990 laying down a Community procedure for the establishment of maximum residue limits of veterinary medicinal products in foodstuffs of animal origin. Off J Eur Communities L224:1-8.
41. 96/23/EC. 1996. Council Directive 96/23/EC of 29 April 1996 on measures to monitor certain substances and residues thereof in live animals and animal products and repealing Directives 85/358/EEC and 86/469/EEC and Decisions 89/187/EEC and 91/664/EEC. Off J Eur Communities L125:10-32.
42. 2821/98/EC. 1998. Council Regulation (EC) No 2821/98 of 17 December 1998 amending, as regards withdrawal of the authorisation of certain antibiotics, Directive 70/524/EEC concerning additives in feeding-stuffs. Off J Eur Communities L351:4-8.
43. 2002/657/EC. 2002. Commission Decision of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Communities L221:8-36.
44. Edder P, Coppex L, Cominoli A, Corvi C. 2002. Analysis of erythromycin and oleandomycin residues in food by high-performance liquid chromatography with fluorometric detection. Food Addit Contam 19:232-240.
45. EMEA. 2008. The European Agency for the Evaluation of Medicinal Products. Veterinary Medicines and Information Technology Unit. Committee for Veterinary Medicinal Products, http://www.emea.europa.eu/index/indexv1.htm.
46. EPA. 1996. Guide to method flexibility and approval of EPA water methods. Washington, DC: Engineering and Analysis Division. Office of. Science and Technology. Office of Water. U.S. Environmental Protection Agency. December 1996. http://www.epa.gov/waterscience/methods/atp/flex.html.
47. EPA. 1999. Protocol for EPA approval of new methods for organic and inorganic analytes in wastewater and drinking water. Washington, DC: U.S. Environmental Protection Agency. Office of Water. Engineering and Analysis Division. March 1999. http://www.epa.gov/waterscience/methods/atp/flex.html.
48. Erah PO, Barrett DA, Shaw PN. 1996. Ion-pair high-performance liquid chromatographic assay method for the assessment of clarithromycin stability in aqueous solution and in gastric juice. J Chromatogr B 682:73-78.
49. EURACHEM. 1998. The Fitness for Purpose of Analytical Methods. A Laboratory Guide to Method Validation and Related Topics. http://www.eurachem. org/guides/valid.pdf.
50. EURACHEM/CITAC. 2000. EURACHEM/CITAC guide: Quantifying uncertainty in analytical measurement. 2nd edition. http://www.eurachem.org/guides/QUAM2000-1. pdf.
51. FAO/WHO. 2008. CODEX alimentarius: Veterinary Drug Residues in Food Maximum. Residue Limits, http://www.codexalimentarius.net/mrls/vetdrugs/jsp/ vetd-q-e.jsp.
52. Farre M, Gros M, Hernandez B, Petrovic M, Hancock P, Barcelo D. 2008. Analysis of biologically active compounds in water by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 22:41-51.
53. FDA. 1996. Guidance for Industry. Q2B Validation of Analytical Procedures: Methodology. U.S. Department of Health and Human Services. Food and Drug Administration. Center for Drug Evaluation and Research (CDER). Center for Biologics Evaluation and Research (CBER). November 1996. ICH. http://www.fda.gov/cder/guidance/1320fnl.pdf.
54. FDA. 1999. Guidance for Industry. Validation of Analytical Procedures: Methodology. FINAL GUIDANCE. U.S. Department of Health and Human Services. Food and Drug Administration. Center for Veterinary Medicine. July 1999. http://www.fda.gov/cvm/guidance/guida64.pdf.
55. FDA. 2001. Guidance for industry. Bioanalytical method validation. U.S. Department of Health and Human. Services. Food and Drug Administration. Center for Drug Evaluation and Research (CDER). Center for Veterinary Medicine (CVM). May 2001. BP. http://www.fda.gov/cder/guidance/4252fnl.htm.
56. FDA. 2003. Guidance for Industry. Mass Spectrometry for Confirmation of the Identity of Animal Drug Residues. FINAL GUIDANCE. U.S. Department of Health and Human Services Food and Drug Administration Center for Veterinary Medicine. May 1 2003. http://www.fda.gov/cvm/guidance/guide118.pdf.
57. FDA. 2008. FDA Center for Veterinary Medicine: Database of Approved Animal Drug Products, http://dil.vetmed.vt.edu/.
58. Ferrer I, García-Reyes JF, Mezcua M, Thurman EM, Fernández-Alba AR. 2005. Multi-residue pesticide analysis in fruits and vegetables by liquid chromatography-time-of-flight mass spectrometry. J Chromatogr A 1082:81-90.
59. Florea NF, Nightingale CH. 2004. Review of the pharmacodynamics of antibiotic use in animal food production. Diagn Microbiol Infect Dis 49:105-108.
60. Foulds G, Shepard RM, Johnson RB. 1990. The pharmacokinetics of azithromycin in human serum and tissues. J Antimicrob Chemother 25(Suppl A):73-82.
61. Galer D, Hessong S, Beato B, Risk J, Inskeep P, Weerasinghe C, Schneider RP, Langer C, LaPerle J, Renouf D, Bessire A, Espanol E, Rafka R, Ragan C, Boettner W, Murphy T, Keller D, Benchaoui H, Nowakowski MA. 2004. An analytical method for the analysis of tulathromycin, an equilibrating triamilide, in bovine and porcine plasma and lung. J Agric Food Chem 52:2179-2191.
62. Gallis HA, Drew RH, Pickard WW. 1990. Amphotericin B: 30 years of clinical experience. Rev Infect Dis 12:308-329.
63. Garcia-Reyes JF, Hernando MD, Ferrer C, Molina-Diaz A, Fernandez-Alba AR. 2007a. Large scale pesticide multiresidue methods in food combining liquid chromatography-time-of-flight mass spectrometry and tandem mass spectrometry. Anal Chem 79:7308-7323.
64. Garcia-Reyes JF, Hernando MD, Molina-Diaz A, Fernandez-Alba AR. 2007b. Comprehensive screening of target, non-target and unknown pesticides in food by LC-TOF-MS. Trends Anal Chem 26:828-841.
65. Gobel A, McArdell CS, Suter MJ, Giger W. 2004. Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem 76:4756-4764.
66. Gobel A, Thomsen A, McArdell CS, Alder AC, Giger W, Theiss N, Loffler D, Ternes TA. 2005. Extraction and determination of sulfonamides, macrolides, and trimethoprim in sewage sludge. J Chromatogr A 1085: 179-189.
67. Gomez MJ, Malato O, Ferrer I, Aguera A, Fernandez-Alba AR. 2007. Solid-phase extraction followed by liquid chromatography-time-of-flight-mass spectrometry to evaluate pharmaceuticals in effluents. A pilot monitoring study. J Environ Monit 9:718-729.
68. Gonzalez de la Huebra MJ, Bordin G, Rodriguez AR. 2003. Comparative study of coulometric and amperometric detection for the determination of macrolides in human urine using high-performance liquid chromatography. Anal Bioanal Chem 375:1031-1037.
69. Gonzalez de la Huebra MJ, Vincent U, Bordin G, Rodríguez AR. 2004. Characterisation of dirithromycin and spiramycin using high performance liquid chromatography and direct infusion mass spectrometry. Anal Chim Acta 503:247-256.
70. Gonzalez de la Huebra MJ, Vincent U. 2005. Analysis of macrolide antibiotics by liquid chromatography. J Pharm Biomed Anal 39:376-398.
71. Govaerts C, Chepkwony HK, Schepdael AV, Roets E, Hoogmartens J. 2000. Investigation of unknown related substances in commercial erythromycin samples with liquid chromatography/mass spectrometry. Rapid Commun Mass Spectrom 14:878-884.
72. Govaerts C, Chepkwony HK, Van Schepdael A, Adams E, Roets E, Hoogmartens J. 2004. Application of liquid chromatography-ion trap mass spectrometry to the characterization of the 16-membered ring macrolide josamycin propionate. J Mass Spectrom 39:437-446.
73. Granelli K, Branzell C. 2007. Rapid multi-residue screening of antibiotics in muscle and kidney by liquid chromatography-electrospray ionization-tandem mass spectrometry. Anal Chim. Acta 586:289-295.
74. Groll AH, Piscitelli SC, Walsh TJ. 1998. Clinical pharmacology of systemic antifungal agents: A comprehensive review of agents in clinical use, current investigational compounds, and putative targets for antifungal drug development. Adv Pharmacol 44:343-500.
75. Gros M, Petrovic M, Barcelo D. 2006. Multi-residue analytical methods using LC-tandem MS for the determination of pharmaceuticals in environmental and wastewater samples: A review. Anal Bioanal Chem 386: 941-952.
76. Gu Y, Wang G, Sun J. 2006. Simultaneous determination of erythromycin ethylsuccinate and its metabolite erythromycin in human plasma using liquid chromatography-electrospray ionization mass spectrometry for clinical study. J Pharm Biomed Anal 40:737-743.
77. Guilhaus M, Selby D, Mlynski V. 2000. Orthogonal acceleration time-of-flight mass spectrometry. Mass Spectrom Rev 19:65-107.
78. Guillarme D, Nguyen DT, Rudaz S, Veuthey JL. 2007. Recent developments in liquid chromatography - Impact on qualitative and quantitative performance. J Chromatogr A 1149:20-29.
79. Gustavsson SA, Samskog J, Markides KE, Langstrom B. 2001. Studies of signal suppression in liquid chromatography-electrospray ionization mass spectrometry using volatile ion-pairing reagents. J Chromatogr A 937:41-47.
80. Hager JW. 2002. A new linear ion trap mass spectrometer. Rapid Commun Mass Spectrom 16:512-526.
81. Hager JW, Yves Le Blanc JC. 2003a. High-performance liquid chromatography-tandem mass spectrometry with a new quadrupole/linear ion trap instrument. J Chromatogr A 1020:3-9.
82. Hager JW, Yves Le Blanc JC. 2003b. Product ion scanning using a Q-q-Q linear ion trap (Q TRAP) mass spectrometer. Rapid Commun Mass Spectrom 17:1056-1064.
83. Haghedooren E, Raju VSK, Dehouck P, Govaerts C, Schepdael AV, Hoogmartens J, Adams E. 2006. Investigation of degradation products in a topical gel containing erythromycin and benzoyl peroxide by liquid chromatography-mass spectrometry. J Pharm Biomed Anal 41:165-175.
84. Hamilton-Miller JM. 1973. Chemistry and biology of the polyene macrolide antibiotics. Bacteriol Rev 37:166-196.
85. Hammel YA, Mohamed R, Gremaud E, Lebreton MH, Guy PA. 2008. Multi-screening approach to monitor and quantify 42 antibiotic residues in honey by liquid chromatography-tandem mass spectrometry. J Chromatogr A 1177:58-76.
86. Hamscher G, Limsuwan S, Tansakul N, Kietzmann M. 2006. Quantitative analysis of tylosin in eggs by high performance liquid chromatography with electrospray ionization tandem mass spectrometry: Residue depletion kinetics after administration via feed and drinking water in laying hens. J Agric Food Chem 54:9017-9023.
87. Hang TJ, Zhang M, Song M, Shen JP, Zhang YD. 2007. Simultaneous determination and pharmacokinetic study of roxithromycin and ambroxol hydrochloride in human plasma by LC-MS/MS. Clin Chim Acta 382:20-24.
88. Hao C, Lissemore L, Nguyen B, Kleywegt S, Yang P, Solomon K. 2006. Determination of pharmaceuticals in environmental waters by liquid chromatography/electrospray ionization/tandem mass spectrometry. Anal Bioanal Chem 384:505-513.
89. Hao C, Clement R, Yang P. 2007. Liquid chromatography-tandem mass spectrometry of bioactive pharmaceutical compounds in the aquatic environment - A decade's activities. Anal Bioanal Chem 387:1247-1257.
90. HC. 2008a. Health Canada. WRLs in honey. http://hc-sc.gc.ca/dhp-mps/ legislation/vet/pol/cfia-acia-amr-ram-table-e.html.
91. HC. 2008b. Health Canada. Drugs & Health Products, Veterinary Drugs, Administrative Maximum Residue Limits (AMRLS) and Maximum Residue Limits (MRLS) set by Canada. http://www.hc-sc.gc.ca/dhp-mps/vet/mrl-lmr/mrl-lmr-versus-new- nouveau-e.html.
92. Heberer T. 2002. Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: A review of recent research data. Toxicol Lett 131:5-17.
93. Heberer T, Reddersen K, Mechlinski A. 2002. From municipal sewage to drinking water: Fate and removal of pharmaceutical residues in the aquatic environment in urban areas. Water Sci Technol 46:81-88.
94. Heller DN, Nochetto CB. 2004. Development of multiclass methods for drug residues in eggs: Silica SPE cleanup and LC-MS/MS analysis of ionophore and macrolide residues. J Agric Food Chem 52:6848-6856.
95. Hernandez F, Ibanez M, Sancho JV, Pozo OJ. 2004. Comparison of different mass spectrometric techniques combined with liquid chromatography for confirmation of pesticides in environmental water based on the use of identification points. Anal Chem 76:4349-4357.
96. Hernandez F, Sancho JV, Pozo OJ. 2005. Critical review of the application of liquid chromatography/mass spectrometry to the determination of pesticide residues in biological samples. Anal Bioanal Chem 382:934-946.
97. Horie M. 1995. Chapter 6. Chemical analysis of macrolides. In: Oka H, Nakazawa H, Harada K, MacNeil JD, editors. Chemical analysis for antibiotics used in agriculture. Arlington, VA: AOAC International, pp. 165-205.
98. Horie M, Saito K, Ishii R, Yoshida T, Haramaki Y, Nakazawa H. 1998. Simultaneous determination of five macrolide antibiotics in meat by high-performance liquid chromatography. J Chromatogr A 812:295-302.
99. Horie M, Takegami H, Toya K, Nakazawa H. 2003. Determination of macrolide antibiotics in meat and fish by liquid chromatography-electrospray mass spectrometry. Anal Chim Acta 492:187-197.
100. Hu D, Coats JR. 2007. Aerobic degradation and photolysis of tylosin in water and soil. Environ Toxicol Chem 26:884-889.
101. Hu M, Hu C. 2005. Identification of the components of 16-membered macrolide antibiotics by LC/MS. Anal Chim Acta 535:89-99.
102. ISO. 1993. Guide to the expression of uncertainty in measurement. Geneva: International Standards Organization (ISO).
103. ISO. 2005. ISO/IEC 17025:2005. General requirements for the competence of testing and calibration laboratories.
104. Jacobsen AM, Halling-Sorensen B. 2006. Multi-component analysis of tetracyclines, sulfonamides and tylosin in swine manure by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem 384: 1164-1174.
105. Jacobsen AM, Halling-Sorensen B, Ingerslev F, Hansen SH. 2004. Simultaneous extraction of tetracycline, macrolide and sulfonamide antibiotics from agricultural soils using pressurised liquid extraction, followed by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Chromatogr A 1038:157-170.
106. Jiang Y, Wang J, Li H, Wang Y, Gu J. 2007. Determination of clarithromycin in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry. J Pharm Biomed Anal 43:1460-1464.
107. Kanfer I, Skinner MF, Walker RB. 1998. Analysis of macrolide antibiotics. J Chromatogr A 812:255-286.
108. Kaufmann A, Butcher P, Maden K, Widmer M. 2007. Ultra-performance liquid chromatography coupled to time of flight mass spectrometry (UPLC-TOF): A novel tool for multiresidue screening of veterinary drugs in urine. Anal Chim Acta 586:13-21.
109. 2 for quantifying trace amounts of pharmaceutical compounds in soil and sediment matrices. Trends Anal Chem 24:635-644.
110. Kim SC, Carlson K. 2007a. Temporal and spatial trends in the occurrence of human and veterinary antibiotics in aqueous and river sediment matrices. Environ Sci Technol 41:50-57.
111. Kim SC, Carlson K. 2007b. Quantification of human and veterinary antibiotics in water and sediment using SPE/LC/MS/MS. Anal Bioanal Chem 387:1301-1315.
112. Kim YH, Heinze TM, Beger R, Pothuluri JV, Cerniglia CE. 2004. A kinetic study on the degradation of erythromycin A in aqueous solution. Int J Pharm 271:63-76.
113. Koch DE, Bhandari A, Closb L, Hunter RP. 2005. Azithromycin extraction from municipal wastewater and quantitation using liquid chromatography/mass spectrometry. J Chromatogr A 1074:17-22.
114. Kochansky J. 2004. Degradation of tylosin residues in honey. J Apicul Res 43:65-68.
115. Koike S, Krapac IG, Oliver HD, Yannarell AC, Chee-Sanford JC, Aminov RI, Mackie RI. 2007. Monitoring and source tracking of tetracycline resistance genes in lagoons and groundwater adjacent to swine production facilities over a 3-year period. Appl Environ Microbiol 73:4813-4823.
116. Lai CC, Tsai PL, Yu C, Her GR. 2000. Analysis of a commercial preparation of erythromycin estolates by tandem mass spectrometry and high performance liquid chromatography/electrospray ionization tandem mass spectrometry using an ion trap mass spectrometer. Rapid Commun Mass Spectrom 14:468-475.
117. Langtry HD, Brogden RN. 1997. Clarithromycin. A review of its efficacy in the treatment of respiratory tract infections in immunocompetent patients. Drugs 53:973-1004.
118. Lee JW, Petersen ME, Lin P, Dressier D, Bekersky I. 2001. Quantitation of free and total amphotericin B in human biologic matrices by a liquid chromatography tandem mass spectrometric method. Ther Drug Monit 23:268-276.
119. Leonard S, Ferraro M, Adams E, Hoogmartens J, Van Schepdael A. 2006. Application of liquid chromatography/ion trap mass spectrometry to the characterization of the related substances of clarithromycin. Rapid Commun Mass Spectrom 20:3101-3110.
120. Leroy P, Decolin D, Nicolas A, Archimbault P. 1994. Determination of josamycin residues in porcine tissues using high-performance liquid chromatography with pre-column derivatization and spectrofluorimetric detection. Analyst 119:2743-2747.
121. Li W, Rettig J, Jiang X, Francisco DT, Naidong W. 2006. Liquid chromatographic-electrospray tandem mass spectrometric determination of clarithromycin in human plasma. Biomed Chromatogr 20:1242-1251.
122. Lim JH, Park BK, Yun HI. 2003. Determination of roxithromycin by liquid chromatography/mass spectrometry after multiple-dose oral administration in broilers. J Vet Sci 4:35-39.
123. Lin CE, Chang CC, Lin WC. 1997. Migration behavior and separation of sulfonamides in capillary zone electrophoresis. III. Citrate buffer as a background electolyte. J Chromatogr A 768:105-112.
124. Lindberg RH, Wennberg P, Johansson MI, Tysklind M, Andersson BA. 2005. Screening of human antibiotic substances and determination of weekly mass flows in five sewage treatment plants in Sweden. Environ Sci Technol 39:3421-3429.
125. Liu F, Xu Y, Huang J, Gao S, Guo Q. 2007. Sensitive liquid chromatography/mass spectrometry assay for the quantification of azithromycin in human plasma. Biomed Chromatogr 21:1272-1278.
126. Loffler D, Ternes TA. 2003. Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry. J Chromatogr A 1021:133-144.
127. Lucchetti D, Fabrizi L, Esposito A, Guandalini E, Di Pasquale M, Coni E. 2005. Simple confirmatory method for the determination of erythromycin residues in trout: A fast liquid-liquid extraction followed by liquid chromatography-tandem mass spectrometry. J Agric Food Chem 53:9689-9694.
128. Maroto A, Boque R, Riu J, Rius FX. 2001. Measurement uncertainty in analytical methods in which trueness is assessed from recovery assays. Anal Chim Acta 440:171-184.
129. Mathur S, Singh R. 2005. Antibiotic resistance in food lactic acid bacteria - A review. Int J Food Microbiol 105:281-295.
130. Matuszewski BK, Constanzer ML, Chavez-Eng CM, 1998. Matrix effect in quantitative LC/MS/MS analyses of biological fluids: A method for determination of finasteride in human plasma at picogram per milliliter concentrations. Anal Chem 70:882-889.
131. Matuszewski BK, Constanzer ML, Chavez-Eng CM. 2003. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal Chem 75:3019-3030.
132. Maul JD, Schuler LJ, Beiden JB, Whiles MR, Lydy MJ. 2006. Effects of the antibiotic ciprofloxacin on stream microbial communities and detritivorous macroinvertebrates. Environ Toxicol Chem 25:1598-1606.
133. McArdell CS, Molnar E, Suter MJF, Giger W. 2003. Occurrence and fate of macrolide antibiotics in wastewater treatment plants and in the Glatt Valley watershed, Switzerland. Environ Sci Technol 37:5479-5486.
134. McClure EL, Wong CS. 2007. Solid phase microextraction of macrolide, trimethoprim, and sulfonamide antibiotics in wastewaters. J Chromatogr A 1169:53-62.
135. Mellon M, Benbrook C, Benbrook KL. 2001a. Hogging it: Estimates of Antimicrobial Abuse in Livestock. Union of Concerned Scientists. Two Brattle Square. Cambridge, MA: UCS Publications. p. 60.
136. Mellon M, Benbrook C, Benbrook KL. 2001b. Hogging it: Estimates of antimicrobial abuse in livestock. Union of concerned scientists. Two brattle square. Cambridge, MA: UCS Publications, p. 1.
137. Merck. 2004. The Merck Index CD Thirteenth Edition. Copyright 2001, 2004 by Merck & Co., Inc., Whitehouse, NJ.
138. Miao XS, Metcalfe CD. 2003. Determination of pharmaceuticals in aqueous samples using positive and negative voltage switching microbore liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrom 38:27-34.
139. Miao XS, Bishay F, Chen M, Metcalfe CD. 2004. Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada. Environ Sci Technol 38:3533-3541.
140. Nakayama I. 1984. Chapter 7. Macrolides in clinical practice. In: Omura S, editor. Macrolide antibiotics: Chemistry, biology, and practice. New York: Academic Press Inc. pp. 261-300.
141. Nalda MJN, Yague JLB, Gomez MTM, Sevilla JJJ, del Nozal JB, Pascual MH. 2006. Trace analysis of antibacterial tylosin A, B, C, and D in honey by liquid chromatography-electrospray ionization-mass spectrometry. J Sep Sci 29:405-413.
142. Omura S, Tanaka H. 1984. Chapter 9. Production, structure, and antifungal activity of polyene macrolides. In: Omura S, editor. Macrolide antibiotics: Chemistry, biology, and practice. New York: Academic Press Inc. pp. 351-404.
143. Peters DH, Clissold SP. 1992. Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs 44:117-164.
144. Petrovic M, Hernando MD, Diaz-Cruz MS, Barcelo D. 2005. Liquid chromatography-tandem mass spectrometry for the analysis of pharmaceutical residues in environmental samples: A review. J Chromatogr A 1067:1-14.
145. Petrovic M, Barcelo D. 2006. Application of liquid chromatography/ quadrupole time-of-flight mass spectrometry (LC-QqTOF-MS) in the environmental analysis. J Mass Spectrom 41:1259-1267.
146. Petrovic M, Gros M, Barcelo D. 2006. Multi-residue analysis of pharmaceuticals in wastewater by ultra-performance liquid chromatography- quadrupole-time-of-flight mass spectrometry. J Chromatogr A 1124:68-81.
147. Pico Y, Blasco C, Font G. 2004. Environmental and food applications of LC-tandem mass spectrometry in pesticide-residue analysis: An overview. Mass Spectrom Rev 23:45-85.
148. Qiang Z, Adams C. 2004. Potentiometric determination of acid dissociation constants (pKa) for human and veterinary antibiotics. Water Res 38:2874-2890.
149. Sacher F, Lange FT, Brauch HJ, Blankenhorn I. 2001. Pharmaceuticals in groundwaters analytical methods and results of a monitoring program in Baden-Wurttemberg, Germany. J Chromatogr A 938:199-210.
150. Sagan C, Salvador A, Dubreuil D, Poulet PP, Duffaut D, Brumpt I, 2005. Simultaneous determination of metronidazole and spiramycin I in human plasma, saliva and gingival crevicular fluid by LC-MS/MS. J Pharm Biomed Anal 38:298-306.
151. Sastre Torano J, Guchelaar HJ. 1998. Quantitative determination of the macrolide antibiotics erythromycin, roxithromycin, azithromycin and clarithromycin in human serum by high-performance liquid chromatography using pre-column derivatization with 9-fluorenylmethyloxycarbonyl chloride and fluorescence detection. J Chromatogr B 720: 89-97.
152. Schaffner CP. 1984. Chapter 12. Polyene macrolides in clinical practice: Pharmacology and adverse and other effects. In: Omura S, editor. Macrolide antibiotics: Chemistry, biology, and practice. New York: Academic Press Inc. pp. 457-507.
153. Scheuch E, Gießmann T, Siegmund W. 2006. Quantitative determination of nystatin in human plasma using LC-MS after inhalative administration in healthy subjects. J Chromatogr B 844:84-88.
154. Scheuch E, Spieker J, Venner M, Siegmund W. 2007. Quantitative determination of the macrolide antibiotic tulathromycin in plasma and broncho-alveolar cells of foals using tandem mass spectrometry. J Chromatogr B 850:464-470.
155. Schlusener MP, Bester K. 2005. Determination of steroid hormones, hormone conjugates and macrolide antibiotics in influents and effluents of sewage treatment plants utilising high-performance liquid chromatography/tandem mass spectrometry with electrospray and atmospheric pressure chemical ionisation. Rapid Commun Mass Spectrom 19: 3269-3278.
156. Schlusener MP, Bester K, Spiteller M. 2003. Determination of antibiotics such as macrolides, ionophores and tiamulin in liquid manure by HPLC-MS/MS. Anal Bioanal Chem 375:942-947.
157. Schlusener MP, Spiteller M, Bester K. 2003. Determination of antibiotics from soil by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry. J Chromatogr A 1003:21-28.
158. Schmitt H, van Beelen P, Tolls J, van Leeuwen CL. 2004. Pollution-induced community tolerance of soil microbial communities caused by the antibiotic sulfachloropyridazine. Environ Sci. Technol 38:1148-1153.
159. Schuhmacher R, Sulyok M, Krska R. 2008. Recent developments in the application of liquid chromatography-tandem mass spectrometry for the determination of organic residues and contaminants. Anal Bioanal Chem 390:253-256.
160. Segura PA, Garcia-Ac A, Lajeunesse A, Ghosh D, Gagnon C, Sauve S. 2007. Determination of six anti-infectives in wastewater using tandem solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Environ Monit 9:307-313.
161. Soler C, Hamilton B, Furey A, James KJ, Manes J, Pico Y. 2006. Comparison of four mass analyzers for determining carbosulfan and its metabolites in citrus by liquid chromatography/mass spectrometry. Rapid Commun Mass Spectrom 20:2151-2164.
162. Song W, Huang M, Rumbeiha W, Li H. 2007. Determination of amprolium, carbadox, monensin, and tylosin in surface water by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 21:1944-1950.
163. Sparkman OD. 2006a. Mass spectrometry desk reference. Pittsburgh, Pennsylvania: Global View Publishing. p. 11.
164. Sparkman OD. 2006b. Mass spectrometry desk reference. Pittsburgh, Pennsylvania: Global View Publishing. p. 98.
165. Sparkman OD. 2006c. Mass spectrometry desk reference. Pittsburgh, Pennsylvania: Global View Publishing, p. 99.
166. Stolker AA, Niesing W, Fuchs R, Vreeken RJ, Niessen WM, Brinkman UA. 2004a. Liquid chromatography with triple-quadrupole and quadrupole-time-of- flight mass spectrometry for the determination of microconstituents - A comparison. Anal Bioanal Chem 378:1754-1761.
167. Stolker AA, Niesing W, Hogendoorn EA, Versteegh JF, Fuchs R, Brinkman UA. 2004b. Liquid chromatography with triple-quadrupole or quadrupole-time of flight mass spectrometry for screening and confirmation of residues of pharmaceuticals in water. Anal Bioanal Chem 378:955-963.
168. Tang QJ, Ling DK, Shen YZ, Chang JR, Wang W. 1989. Studies on the isolation, identification and bioactivity of a degradation product of erythromycin lactobionate. Yao Wu Fen Xi Za Zhi 9:85-90.
169. Tang HP, Ho C, Lai SS. 2006. High-throughput screening for multi-class veterinary drug residues in animal muscle using liquid chromatography/tandem mass spectrometry with on-line solid-phase extraction. Rapid Commun Mass Spectrom 20:2565-2572.
170. Thiele-Bruhn S. 2003. Pharmaceutical antibiotic compounds in soils - A review. J Plant Nutr Soil Sci 166:145-167.
171. Thompson M, Ellison SL, Fajgelj A, Willetts P, Wood R. 1999. Harmonized guidelines for the use of recovery information in analytical measurement. Pure Appl Chem 71:337-348.
172. Thompson M, Ellison SLR, Wood R. 2002. Harmonized guidelines for single-laboratory validation of methods of analysis. Pure Appl. Chem 74:835-855.
173. Thompson TS, Noot DK, Calvert J, Pernal SF. 2003. Determination of lincomycin and tylosin residues in honey using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J Chromatogr A .1020:241-250.
174. Thompson TS, Noot DK, Calvert J, Pernal SF. 2005. Determination of lincomycin and tylosin residues in honey by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 19:309-316.
175. Thompson TS, Pernal SF, Noot DK, Melathopoulos AP, van den Heever JP. 2007. Degradation of incurred tylosin to desmycosin - Implications for residue analysis of honey. Anal Chim Acta 586:304-311.
176. Thurman EM, Ferrer I, Fernandez-Alba AR. 2005. Matching unknown empirical formulas to chemical structure using LC/MS TOF accurate mass and database searching: Example of unknown pesticides on tomato skins. J Chromatogr A 1067:127-134.
177. Van Poucke C, De Keyser K, Baltusnikiene A, McEvoy JDG, Van Peteghem C. 2003. Liquid chromatographic-tandem mass spectrometric detection of banned antibacterial growth promoters in animal feed. Anal Chim Acta 483:99-109.
178. Van Poucke C, Dumoulin F, De Keyser K, Elliott C, Van Peteghem C. 2004. Tylosin detection in animal feed by liquid chromatography-tandem mass spectrometry with enzymatic hydrolysis of the tylosin urea adduct. J Agric Food Chem 52:2803-2806.
179. Van Poucke C, Dumoulin F, Van Peteghem C. 2005. Detection of banned antibacterial growth promoters in animal feed by liquid chromatography-tandem mass spectrometry: Optimisation of the extraction solvent by experimental design. Anal Chim Acta 529:211-220.
180. van Rooyen GF, Smit MJ, De Jager AD, Hundt HK, Swart KJ, Hundt AF. 2002. Sensitive liquid chromatography-tandem mass spectrometry method for the determination of clarithromycin in human plasma. J Chromatogr B 768:223-229.
181. Viswanathan CT, Bansal S, Booth B, DeStefano AJ, Rose MJ, Sailstad J, Shah VP, Skelly JP, Swann PG, Weiner R. 2007. Workshop/Conference Report - Quantitative Bioanalytical Methods Validation and Implementation: Best Practices for Chromatographic and Ligand Binding Assays. AAPS J 9: E30-E42.
182. Wang J. 2004. Determination of five macrolide antibiotic residues in honey by LC-ESI-MS and LC-ESI-MS/MS. J Agric Food Chem 52: 171-181.
183. Wang J, Cheung W, Grant D. 2005. Determination of pesticides in apple-based infant foods using liquid chromatography electrospray ionization tandem mass spectrometry. J Agric Food Chem 53: 528-537.
184. Wang J, Leung D, Butterworth F. 2005. Determination of five macrolide antibiotic residues in eggs using liquid chromatography/electrospray ionization tandem mass spectrometry. J Agric Food Chem 53: 1857-1865.
185. Wang P, Qi M, Jin X. 2005. Determination of roxithromycin in rat lung tissue by liquid chromatography-mass spectrometry. J Pharm Biomed Anal 39: 618-623.
186. Wang J, Cheung W. 2006. Determination of pesticides in soy-based infant formula using liquid chromatography with electrospray ionization tandem mass spectrometry. J AOAC Int 89: 214-224.
187. Wang J, Leung D, Lenz SP. 2006. Determination of five macrolide antibiotic residues in raw milk using liquid chromatography-electrospray ionization tandem mass spectrometry. J Agric Food Chem 54: 2873-2880.
188. Wang J, Leung D. 2007. Analyses of macrolide antibiotic residues in eggs, raw milk, and honey using both ultra-performance liquid chromatography/ quadrupole time-of-flight mass spectrometry and high-performance liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 21: 3213-3222.
189. Whittle G, Whitehead TR, Hamburger N, Shoemaker NB, Cotta MA, Salyers AA. 2003. Identification of a new ribosomal protection type of tetracycline resistance gene, tet(36), from swine manure pits. Appl Environ Microbiol 69:4151-4158.
190. Williamson LN, Bartlett MG. 2007. Quantitative liquid chromatography/time-of-flight mass spectrometry. Biomed Chromatogr 21:567-576.
191. Wilson RC. 1984. Chapter 8. Macrolides in veterinary practice. In: Omura S, editor. Macrolide antibiotics: Chemistry, biology, and practice. New York: Academic Press Inc. p 301-347.
192. Xiao W, Chen B, Yao S, Cheng Z. 2005. Simultaneous determination of erythromycin propionate and base in human plasma by high-performance liquid chromatography-electrospray mass spectrometry. J Chromatogr B 817:153-158.
193. Xu WH, Zhang G, Zou SC, Li XD, Liu YC. 2007. Determination of selected antibiotics in the Victoria Harbour and the Pearl River, South China using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Environ Pollut 145:672-679.
194. Yang S, Carlson KH. 2004. Solid-phase extraction-high-performance liquid chromatography-ion trap mass spectrometry for analysis of trace concentrations of macrolide antibiotics in natural and waste water matrices. J Chromatogr A 1038:141-155.
195. Yang S, Cha J, Carlson K. 2006. Trace analysis and occurrence of anhydroerythromycin and tylosin in influent and effluent wastewater by liquid chromatography combined with electrospray tandem mass spectrometry. Anal Bioanal Chem 385:623-636.
196. Yasojima M, Nakada N, Komori K, Suzuki Y, Tanaka H. 2006. Occurrence of levofloxacin, clarithromycin and azithromycin in wastewater treatment plant in Japan. Water Sci Technol 53:227-233.
197. Ye Z, Weinberg HS, Meyer MT. 2007. Trace analysis of trimethoprim and sulfonamide, macrolide, quinolone, and tetracycline antibiotics in chlorinated drinking water using liquid chromatography electrospray tandem mass spectrometry. Anal Chem 79:1135-1144.
198. Zhong D, Li X, Wang A, Xu Y, Wu S. 2000. Identification of the metabolites of roxithromycin in humans. Drug Metab Dispos 28:552-559.
199. Zhong D, Shi X, Sun L, Chen X. 2003. Determination of three major components of bitespiramycin and their major active metabolites in rat plasma by liquid chromatography-ion trap mass spectrometry. J Chromatogr B 791:45-53.
200. Zotchev SB. 2003. Polyene macrolide antibiotics and their applications in human therapy. Curr Med Chem 10:211-223.
201. Zwiener C, Frimmel FH. 2004a. LC-MS analysis in the aquatic environment and in water treatment - A critical review. Part I: Instrumentation and general aspects of analysis and detection. Anal Bioanal Chem 378:851-861.
202. Zwiener C, Frimmel FH. 2004b. LC-MS analysis in the aquatic environment and in water treatment technology - A critical review. Part II: Applications for emerging contaminants and related pollutants, microorganisms and humic acids. Anal Bioanal Chem 378:862-874.