Identification and Synthesis of an Oxidation Product of Tilmicosin

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 8, 1998, Pages 3265-3271

  Willard, Kevin E ^a   Kirst, Herbert A ^a   Leeds, James P ^a   Readnour, Robin S ^a   Klink, Paul R ^a   Cleveland, Christine M ^a   Kiehl, Douglas E ^a  

^a NONE

Author keywords

Epoxytilmicosin; Liquid chromatography ion spray mass spectrometry; Macrolide; Oxidation; Synthesis; Tilmicosin

Indexed keywords

EID: 0347935637     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9710746     Document Type: Article

References (16)

1. Borch, R. F.; Bernstein, M. D.; Durst, H. D. The Cyanohydridoborate Anion as a Selective Reducing Agent. J. Am. Chem. Soc. 1971, 93, 2897-2904.
2. Debono, M.; Willard, K. E.; Kirst, H. A.; Wind, J. A.; Crouse, G. D.; Tao, E. V.; Vicenzi, J. T.; Counter, F. T.; Ott, J. L.; Ose, E. E.; Omura, S. Synthesis and Antimicrobial Evaluation of 20-Deoxo-20-(3,5-Dimethylpiperidin-1-yl)desmycosin Tilmicosin, EL870) and Related Cyclic Amino Derivatives. J. Antibiot. 1989, 42, 1253-1267.
3. Galyean, M. L.; Gunter, S. A.; Malcolmcallis, K. J. Effects of Arrival Medication with Tilmicosin Phosphate on Health and Performance of Newly Received Beef Cattle. J Anim. Sci. 1995, 73, 1219-1226.
4. Inman, E. L.; Tenbarge, H. J. High-Low Chromatography: Estimating Impurities in HPLC Using a Pair of Sample Injections. J. Chromatogr. Sci. 1988, 26, 89-94.
5. Kabalka, G. W.; Hedgecock, H. C. A Mild and Convenient Oxidation Procedure for the Conversion of Organoboranes to the Corresponding Alcohols. J. Org. Chem. 1975, 40, 1776-1779.
6. Kirst, H. A. Antibiotics (Macrolides). In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Wiley: New York, 1992; Vol. 3, pp 169-213.
7. Kirst, H. A.; Toth, J. E.; Debono, M.; Willard, K. E.; Truedell, B. A.; Ott, J. L.; Counter, F. T.; Felty-Duckworth, A. M.; Pekarek, R. S. Synthesis and Evaluation of Tylosin-Related Macrolides Modified at the Aldehyde Function: A New Series of Orally Effective Antibiotics. J. Med. Chem. 1988, 31, 1631-1641.
8. Kirst, H. A.; Willard, K. E.; Debono, M.; Toth, J. E.; Truedell, B. A.; Leeds, J. P.; Ott, J. L.; Felty-Duckworth, A. M.; Counter, F. T. Structure - Activity Studies of 20-Deoxo-20 Amino Derivatives of Tylosin-Related Macrolides. J. Antibiot. 1989, 42, 1673-1683.
9. Kirst, H. A.; Donoho, A. L.; Creemer, L. C.; Wind, J. A.; Berry, D. M.; Occolowitz, J. L.; Paschal, J. W. Identification and Synthesis of Products Isolated during Metabolism Studies of Tilmicosin. J. Agric. Food Chem. 1994, 42, 1219-1222.
10. Moore, G. M.; Basson, R. P.; Tonkinson, L. V. Clinical Field Trials with Tilmicosin Phosphate in Feed for the Control of Naturally Acquired Pneumonia caused by Actinobacillus pleuropneumoniae and Pasteurella multocida in Swine. Am. J. Vet. Res. 1996a, 57, 224-228.
11. Moore, G. M.; Mowrey, D. H.; Tonkinson, L. V.; Lechtenberg, K. F.; Schneider, J. H. Efficacy Dose Determination Study of Tilmicosin Phosphate in Feed for Control of Pneumonia caused by Actinobacillus pleuropneumoniae in Swine. Am. J. Vet. Res. 1996b, 57, 220-223.
12. Musser, J.; Mechor, G. D.; Grohn, Y. T.; Dubovi, E. J.; Shin, S. Comparison of Tilmicosin with Long-acting Oxytetracycline for Treatment of Respiratory Tract Disease in Calves. J. Am. Vet. Med. Assoc. 1996, 208, 102-106.
13. NCCLS. Performance Standards for Antimicrobial Disk and Dilution Susceptibility Tests for Bacteria Isolated from Animals, Tentative Standard; NCCLS Document M31-T (ISBN 1-56238-330-2); NCCLS: Wayne, PA, 1997.
14. Omura, S., Ed. Macrolide Antibiotics: Chemistry, Biology, and Practice; Academic Press: Orlando, FL, 1984.
15. Ose, E. In Vitro Antibacterial Properties of EL-870, A new Semi-synthetic Macrolide Antibiotic, J. Antibiot. 1987, 40, 190-194.
16. Scott, P. R.; McGowan, M.; Sargison, N. D.; Penny, C. D.; Lowman, B. G. Use of Tilmicosin in a Severe Outbreak of Respiratory Disease in Weaned Beef Calves. Aust. Vet. J. 1996, 73, 62-64.