Thalidomide metabolites in mice and patients with multiple myeloma

Clinical Cancer Research

Volumn 9, Issue 5, 2003, Pages 1680-1688

  Lu, Jun ^a   Palmer, Brian D ^a   Kestell, Phillip ^a   Browett, Peter ^b   Baguley, Bruce C ^a   Muller, George ^c   Ching, Lai Ming ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b THE UNIVERSITY OF AUCKLAND   (New Zealand)

^c CELGENE CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; THALIDOMIDE;

ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CLINICAL ARTICLE; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG HYDROXYLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; MOUSE; MULTIPLE MYELOMA; NONHUMAN; PLASMA; PRIORITY JOURNAL; URINE;

ANGIOGENESIS INHIBITORS; ANIMALS; BIOTRANSFORMATION; CASE-CONTROL STUDIES; CHROMATOGRAPHY, LIQUID; HUMANS; HYDROLYSIS; HYDROXYLATION; MALE; MASS SPECTROMETRY; MICE; MICE, INBRED C57BL; MULTIPLE MYELOMA; THALIDOMIDE;

EID: 0038666418     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Mellin, G. W., and Katzenstein, M. The saga of thalidomide. N. Eng. J. Med., 267: 1238-1244, 1962.
2. Zwingenberger, K., and Wnendt, S. Immunomodulation by thalidomide: systematic review of the literature and of unpublished observations. J. Inflamm., 46: 177-211, 1995.
3. Calabrese, L., and Resztak, K. Thalidomide revisited: pharmacology and clinical applications. Expert Opin. Investig. Drugs, 7: 2043-2060, 1998.
4. Eisen, T. G. Thalidomide in solid tumors: the London experience. Oncology (Huntington), 14: 17-20, 2000.
5. D'Amato, R. J., Loughnan, M. S., Flynn, E., and Folkman, J. Thalidomide is an inhibitor of angiogenesis. Proc. Natl. Acad. Sci. USA, 91: 4082-4085, 1994.
6. Eisen, T., Boshoff, C., Mak, I., Sapunar, F., Vaughan, M. M., Pyle, L., Johnston, S. R., Ahern, R., Smith, I. E., and Gore, M. E. Continuous low dose Thalidomide: a phase II study in advanced melanoma, renal cell, ovarian and breast cancer. Br. J. Cancer, 82: 812-817, 2000.
7. Fine, H. A., Figg, W. D., Jaeckle, K., Wen, P. Y., Kyritsis, A. P., Loeffler, J. S., Levin, V. A., Black, P. M., Kaplan, R., Pluda, J. M., and Yung, W. K. Phase II trial of the antiangiogenic agent thalidomide in patients with recurrent high-grade gliomas. J. Clin. Oncol., 18: 708-715, 2000.
8. Figg, W. D., Raje, S., Bauer, K. S., Tompkins, A., Venzon, D., Bergan, R., Chen, A., Hamilton, M., Pluda, J., and Reed, E. Pharmacokinetics of thalidomide in an elderly prostate cancer population. J. Pharm. Sci., 88: 121-125, 1999.
9. Vacca, A., Ribatti, D., Roncali, L., Ranieri, G., Serio, G., Silvestris, F., and Dammacco, F. Bone marrow angiogenesis and progression in multiple myeloma. Br. J. Haematol., 87: 503-508, 1994.
10. Singhal, S., Mehta, J., Desikan, R., Ayers, D., Roberson, P., Eddlemon, P., Munshi, N., Anaissie, E., Wilson, C., Dhodapkar, M., Zeddis, J., and Barlogie, B. Antitumor activity of thalidomide in refractory multiple myeloma. N. Eng. J. Med., 341: 1565-1571, 1999.
11. Faigle, J. W. The metabolic fate of thalidomide. Experientia, 18: 389-397, 1962.
12. Schumacher, H., Smith, R. L., and Williams, R. T. The metabolism of thalidomide: the fate of thalidomide and some of its hydrolysis products in various species. Br. J. Pharmacol., 25: 338-351, 1965.
13. Schumacher, H., Smith, R. L., and Williams, R. T. The metabolism of thalidomide: the spontaneous hydrolysis of thalidomide in solution. Br. J. Pharmacol., 25: 324-337, 1965.
14. Braun, A. G., Harding, F. A., and Weinreb, S. L. Teratogen metabolism: thalidomide activation is mediated by cytochrome P-450. Toxicol. Appl. Pharmacol., 82: 175-179, 1986.
15. Ando, Y., Fuse, E., and Figg, W. D. Thalidomide metabolism by the CYP2C subfamily. Clin. Cancer Res., 8: 1964-1973, 2002.
16. Eriksson, T., Bjorkman, S., Roth, B., Bjork, H., and Hoglund, P. Hydroxylated metabolites of thalidomide: formation in-vitro and in-vivo in man. J. Pharm. Pharmacol., 50: 1409-1416, 1998.
17. Bauer, K. S., Dixon, S. C., and Figg, W. D. Inhibition of angio-genesis by thalidomide requires metabolic activation, which is species-dependent. Biochem. Pharmacol., 55: 1827-1834, 1998.
18. Eriksson, T., Bjorkman, S., Roth, B., Fyge, A., and Hoglund, P. Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality, 10: 223-228, 1998.
19. Gordon, G. B., Spielberg, S. P., Blake, D. A., and Balasubramanian, V. Thalidomide teratogenesis: evidence for a toxic arene oxide metabolite. Proc. Natl. Acad. Sci. USA, 78: 2545-2548, 1981.
20. Reist, M., Carrupt, P. A., Francotte, E., and Testa, B. Chiral inversion and hydrolysis of thalidomide: mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites. Chem. Res. Toxicol., 11: 1521-1528, 1998.
21. Price, D. K., Ando, Y., Kruger, E. A., Weiss, M., and Figg, W. D. 5′-OH-Thalidomide, a metabolite of thalidomide, inhibits angiogenesis. Ther. Drug Monit., 24: 104-110, 2002.
22. Luzzio, F. A., Thomas, E. M., and Figg, W. D. Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S, 3S (3-hydroxy) ornithine. Tetrahedron Lett., 41: 7151-7155, 2000.
23. Marks, M. G., Shi, J., Fry, M. O., Xiao, Z., Trzyna, M., Pokala, V., Ihnat, M. A., and Li, P. K. Effects of putative hydroxylated thalidomide metabolites on blood vessel density in the chorioallantoic membrane (CAM) assay and on tumor and endothelial cell proliferation. Biol. Pharm. Bull., 25: 597-604, 2002.
24. Kruse, F. E., Joussen, A. M., Rohrschneider, K., Becker, M. D., and Volcker, H. E. Thalidomide inhibits corneal angiogenesis induced by vascular endothelial growth factor. Graefe's Arch. Clin. Exp. Ophthalmol., 236: 461-466, 1998.
25. Kenyon, B. M., Browne, F., and D'Amato, R. J. Effects of thalidomide and related metabolites in a mouse corneal model of neovascularization. Exp. Eye Res., 64: 971-978, 1997.
26. Kaldor, S. W., Hammond, M., Dressman, B. A., Labus, J. M., Chadwell, F. W., Kline, A. D., and Heinz, B. A. Glutamine-derived aldehydes for the inhibition of human rhinovirus 3C protease. Bioorg. Med. Chem. Lett., 5: 2021-2026, 1995.
27. Webster, L. K., Ellis, A. G., Kestell, P., and Rewcastle, G. W. Metabolism and elimination of 5,6-dimethylxanthenone-4-acetic acid in the isolated perfused rat liver. Drug Metab. Dispos., 23: 363-368, 1995.
28. Weinz, C., and Blaschke, G. Investigation of the in vitro biotransformation and simultaneous enantioselective separation of thalidomide and its neutral metabolites by capillary electrophoresis. J. Chromatogr. B Biomed. Appl., 674: 287-292, 1995.
29. Teo, S. K., Sabourin, P. J., O'Brien, K., Kook, K. A., and Thomas, S. D. Metabolism of thalidomide in human microsomes, cloned human cytochrome P-450 isozymes, and Hansen's disease patients. J. Biochem. Mol. Toxicol., 14: 140-147, 2000.
30. Meyring, M., Muhlenbrock, C., and Blaschke, G. Investigation of the stereoselective in vitro biotransformation of thalidomide using a dual cyclodextrin system in capillary electrophoresis. Electrophoresis, 21: 3270-3279, 2000.
31. Williams, M. L., Bhargava, P., Cherrouk, I., Marshall, J. L., Flockhart, D. A., and Wainer, I. W. A discordance of the cytochrome P450 2C19 genotype and phenotype in patients with advanced cancer. Br. J. Clin. Pharmacol., 49: 485-488, 2000.
32. Suzuki, H., Yasukawa, K., Saito, T., Goitsuka, R., Hasegawa, A., Ohsugi, Y., Taga, T., and Kishimoto, T. Anti-human interleukin-6 receptor antibody inhibits human myeloma growth in vivo. Eur. J. Immunol., 22: 1989-1993, 1992.
33. Gupta, D., Treon, S. P., Shima, Y., Hideshima, T., Podar, K., Tai, Y. T., Lin, B., Lentzsch, S., Davies, F. E., Chauhan, D., Schlossman, R. L., Richardson, P., Ralph, P., Wu, L., Payvandi, F., Muller, G., Stirling, D. I., and Anderson, K. C. Adherence of multiple myeloma cells to bone marrow stromal cells upregulates vascular endothelial growth factor secretion: therapeutic applications. Leukemia (Baltimore), 15: 1950-1961, 2001.
34. Dunzendorfer, S., Herold, M., and Wiedermann, C. J. Inducerspecific bidirectional regulation of endothelial interleukin-8 production by thalidomide. Immunopharmacology, 43: 59-64, 1999.
35. Moller, D. R., Wysocka, M., Greenlee, B. M., Ma, X., Wahl, L., Flockhart, D. A., Trinchieri, G., and Karp, C. L. Inhibition of IL-12 production by thalidomide. J. Immunol., 159: 5157-5161, 1997.
36. Rowland, T. L., McHugh, S. M., Deighton, J., Dearman, R. J., Ewan, P. W., and Kimber, I. Differential regulation by thalidomide and dexamethasone of cytokine expression in human peripheral blood mononuclear cells. Immunopharmacology, 40: 11-20, 1998.
37. Sampaio, E. P., Sarno, E. N., Galilly, R., Cohn, Z. A., and Kaplan, G. Thalidomide selectively inhibits tumor necrosis factor α production by stimulated human monocytes. J. Exp. Med., 173: 699-703, 1991.
38. Shannon, E. J., Sandoval, F., and Krahenbuhl, J. L. Hydrolysis of thalidomide abrogates its ability to enhance mononuclear cell synthesis of IL-2 as well as its ability to suppress the synthesis of TNF-α. Immunopharmacology, 36: 9-15, 1997.