Measurement of tacrolimus (FK506) and its metabolites: A review of assay development and application in therapeutic drug monitoring and pharmacokinetic studies

Therapeutic Drug Monitoring

Volumn 19, Issue 3, 1997, Pages 338-351

  Alak, Ala M ^a  

^a Fujisawa Res Institute of America   (United States)

Author keywords

FK506; Metabolites; Pharmacokinetics studies; Tacrolimus; Therapeutic drug monitoring

Indexed keywords

ACETIC ACID ETHYL ESTER; CALCINEURIN; DANSYL CHLORIDE; DICHLOROMETHANE; DRUG METABOLITE; FK 506 BINDING PROTEIN; IMMUNOSUPPRESSIVE AGENT; METHANOL; SULFOSALICYLIC ACID; TACROLIMUS;

BIOASSAY; DERIVATIZATION; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG MECHANISM; DRUG METABOLISM; DRUG MONITORING; DRUG STABILITY; DRUG STRUCTURE; ENZYME LINKED IMMUNOSORBENT ASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IMMUNOASSAY; LYMPHOCYTE PROLIFERATION; MASS SPECTROMETRY; PHARMACOKINETICS; PRIORITY JOURNAL; RADIORECEPTOR ASSAY; REVIEW; SUPERCRITICAL FLUID CHROMATOGRAPHY; T LYMPHOCYTE;

BIOLOGICAL ASSAY; CALCINEURIN; CALMODULIN-BINDING PROTEINS; CARRIER PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DANSYL COMPOUNDS; DNA-BINDING PROTEINS; DRUG MONITORING; ENZYME-LINKED IMMUNOSORBENT ASSAY; FLUORESCENT DYES; HEAT-SHOCK PROTEINS; HUMANS; HYDRAZINES; IMMUNOSUPPRESSIVE AGENTS; MASS SPECTROMETRY; PHOSPHOPROTEIN PHOSPHATASE; TACROLIMUS; TACROLIMUS BINDING PROTEINS;

EID: 0031450768     PISSN: 01634356     EISSN: None     Source Type: Journal    
DOI: 10.1097/00007691-199706000-00016     Document Type: Review

References (47)

1. Goto T, Kino T, Hatanaka H, Nishiyama M, Okuhara M, Kohsaka M, Aoki H, Imanaka H. Discovery of FK-506, a novel immunosuppressant isolated from Streptomyces tsukubaensis. Transplant Proc 1987;19:4-8.
2. Goto T, Kino T, Hatanaka H, Okuhara M, Kohsaka M, Aoki H, Imanaka H. FK 506: historical perspectives. Transplant Proc 1991;23:2713-7.
3. Kino T, Inamura N, Sakai F, Nakahara K, Goto T, Okuhara M, Kohsaka M, Aoki H, Ochiai T. Effect of FK-506 on human mixed lymphocyte reaction in vitro. Transplant Proc 1987; 19:36-9.
4. Peters DH, Fitton A, Plosker GL, Faulds D. Tacrolimus. A review of its pharmacology, and therapeutic potential in hepatic and renal transplantation. Drugs 1993;46:746-94.
5. Morris RE. Mechanisms of action of new immunosuppressive drugs. Ther Drug Monit 1995;17:564-9.
6. Venkataramanan R, Warty VS, Zermaitis MA, Sanghvi AT, Burckart GJ, Seltman H, Todo S, Makowka L, Starzl TE. Biopharmaceutical aspects of FK-506. Transplant Proc 1987;19:30-5.
7. Vincent SH, Karanam BV, Painter SK, Chiu S-HL. In vitro metabolism of FK-506 in rat, rabbit, and human liver microsomes: identification of a major metabolite and of cytochrome P450 3A as the major enzymes responsible for its metabolism. Arch Biochem Biophys 1992;294:454-60.
8. Shiraga T, Matsuda H, Nagase K, Iwasaki K, Noda K, Yamazaki H, Shimada T, Funae Y. Metabolism of FK506, a potent immunosuppressive agent, by cytochrome P450 3A enzymes in rat, dog and human liver microsomes. Biochem Pharmacol 1994;47:7275.
9. Christians U, Kruse C, Kownatzki R, Schiebel HM, Schwinzer R, Sattler M, Schottmann R, Linck A, Almeida VMF, Braun F, Sewing K-Fr. Measurement of FK 506 by HPLC and isolation and characterization of its metabolites. Transplant Proc 1991;23:940-1.
10. Iwasaki K, Shiraga T, Nagase K, Tozuka Z, Noda K, Sakuma S, Fujitsu T, Shimatani K, Sato A, Fujioka M. Isolation, identification, and biological activities of oxidative metabolites of FK506, a potent immunosuppressive macrolide lactone. Drug Metab Dispos Biol Fate Chem 1993;21:971-7.
11. Iwasaki K, Shiraga T, Matsuda H, Nagase K, Tokuma Y, Hata T, Fujii Y, Sakuma S, Fujitsu T, Fujikawa A, Shimatani K, Sato A, Fujioka M. Further metabolism of FK506 (tacrolimus). Identification and biological activities of the metabolites oxidized at multiple sites of FK506. Drug Metab Dispos Biol Fate Chem 1995;23:28-34.
12. Tamura K, Fujimura T, Iwasaki K, Sakuma S, Fujitsu T, Nakamura K, Shiomura K, Kuno T, Tanaka C, Kobayashi M. Interaction of tacrolimus (FK506) and its metabolites with FKBP and calcineurin. Biochem Biophys Res Commun 1994; 202:437-43.
13. 15-demethylated metabolite of FK-506 is governed by ring- and open-chain tautomerism effects. J Pharmacol Exp Ther 1995;274:622-6.
14. Kobayashi M, Tamura K, Katayama N, Nakamura K, Nagase K, Hane K, Tutumi T, Niwa M, Tanaka H, Iwasaki K, Kohsaka M. FK 506 assay past and present - characteristics of the FK 506 ELISA. Transplant Proc 1991;23:2725-9.
15. Van Duyne GD, Standaert RF, Karplus PA, Schreiber SL, Clardy J. Atomic structure of FKBP-FK506, an immunophilin-immunosuppressant complex. Science 1991;252:839-42.
16. Jusko WJ, Thomson AW, Fung J, McMaster P, Wong SH, Zylber-Katz E, Christians U, Winkler M, Fitzsimmons WE, Lieberman R, McBride J, Kobayashi M, Warty V, Soldin SJ. Consensus document: therapeutic drug monitoring of tacrolimus (FK-506). Ther Drug Monit 1995;17:606-14.
17. Lizak P, Alak AM. Stability of FK506 in blood samples. Ther Drug Monit 1996;18:209-11.
18. Jusko WJ. Analysis of tacrolimus (FK 506) in relation to therapeutic drug monitoring. Ther Drug Monit 1995;17:596-601.
19. McMaster P, Mizra DF, Ismail T, Vennarecci G, Patapis P, Mayer AD. Therapeutic drug monitoring of tacrolimus in clinical transplantation. Ther Drug Monit 1995;17:602-5.
20. Cox KL, Lawrence-Miyasaki LS, Gracia-Kennedy R, Lennette ET, Martinez OM, Krams SM, Berquist WE, So SK, Esquivel CO. An increased incidence of Epstein-Barr virus infection and lymphoproliferative disorder in young children on FK506 after liver transplantation. Transplantation 1995;59:524-9.
21. Tamura K, Kobayashi M, Hashimoto K, Kojima K, Nagase K, Iwasaki K, Kaizu T, Tanaka H, Niwa M. A highly sensitive method to assay FK-506 levels in plasma. Transplant Proc 1987;19:23-9.
22. Cadoff EM, Venkataramanan R, Krajack A, Jain AS, Fung JJ, Todo S, Starzl TE. Assay of FK 506 in plasma. Transplant Proc 1990;22:50-1.
23. Jusko WJ, D'Ambrosio R. Monitoring FK 506 concentrations in plasma and whole blood. Transplant Proc 1991;23:2732-5.
24. Beysens AJ, Wijnen RMH, Beuman GH, van der Heyden J, Koostra G, van As H. FK 506: monitoring in plasma or whole blood? Transplant Proc 1991;23:2745-7.
25. Warty VS, Venkataramanan R, Zendehrouh P, Mehta S, McKaveney T, Flowers J, Zuckerman S, Krajak A, Zeevi A, Fung J, Todo S, Starzl TE. Practical aspects of FK 506 analysis (Pittsburgh experience). Transplant Proc 1991;23:2730-1.
26. Wallemacq PE, Firdaous I, Hassoun A. Improvement and assessment of enzyme-linked immunosorbent assay to detect low FK506 concentrations in plasma or whole blood within 6 hours. Clin Chem 1993;39:1045-9.
27. D'Ambrosio R, Jusko WJ, Stabler T, Kobayashi M. Improved procedures for enzyme immunoassay of tacrolimus (FK506) in whole blood. Clin Chem 1994;40:159-60.
28. Alak AM, Cook M, Bekersky I. A highly sensitive ELISA assay for the determination of tacrolimus in whole blood from atopic dermatitis patients. Ther Drug Monit 1997; in press.
29. Grenier FC, Luzkiw J, Bergmann M, Lunetta S, Morrison M, Blonski D, Shoemaker K, Kobayashi M. A whole blood FK 506 assay for the IMx® analyzer. Transplant Proc 1991;23:2748-9.
30. Alak AM, Lizak PP. Quality assurance procedure for monitoring tacrolimus (FK506) concentrations in whole blood by IMx assay. Ther Drug Monit 1996;18:267-72.
31. x analyzer and enzyme immunoassay with methylene chloride extraction. Ther Drug Monit 1994;16:287-92.
32. Winkler M, Christians U, Stoll K, Baumann J, Pichlmayr R. Comparison of different assays for the quantitation of FK 506 levels in blood or plasma. Ther Drug Monit 1994;16:281-6.
33. Perotti BYT, Prueksaritanont T, Benet LZ. HPLC assay for FK 506 and two metabolites in isolated rat hepatocytes and rat liver microsomes. Pharm Res 1994;11:844-7.
34. Takada K, Oh-Hashi M, Yoshikawa H, Muranishi S, Nishiyama M, Yoshida H, Hata T, Tanaka H. Determination of a novel immunosuppressant (FK-506) in rat serum and lymph by high-performance liquid chromatography with chemiluminescence detection. J Chromatogr 1990;530:212-8.
35. Beysens AJ, Beuman GH, van der Heijden JJ, Hoogtanders KEJ, Steijger OM, Lingeman H. Determination of tacrolimus (FK 506) in whole blood using liquid chromatography and fluorescence detection. Chromatographia 1994;39:490-6.
36. Christians U, Braun F, Kosian N, Schmidt M, Schiebel HM, Ernst L, Kruse C, Winkler M, Holze I, Linck A, Sewing K-Fr. High performance liquid chromatography/mass spectrometry of FK 506 and its metabolites in blood, bile, and urine of liver grafted patients. Transplant Proc 1991;23:2741-4.
37. Christians U, Braun F, Schmidt M, Kosian N, Schiebel H-M, Ernst L, Winkler M, Kruse C, Linck A, Sewing K-Fr. Specific and sensitive measurement of FK506 and its metabolites in blood and urine of liver-graft patients. Clin Chem 1992;38:2025-32.
38. Gonschior A-K, Christians U, Winkler M, Schiebel HM, Linck A, Sewing K-Fr. Simplified high-performance liquid chromatography-mass spectrometry assay for measurement of tacrolimus and its metabolites and cross-validation with microparticle enzyme immunoassay. Ther Drug Monit 1995;17:504-10.
39. Lhoëst G, Wallemacq P, Verbeeck R. Isolation and mass spectrometric identification of five metabolites of FK-506, a novel immunosuppressive agent, from human plasma. Pharm Acta Helv 1991;66:302-6.
40. Wong SHY, Ghodgaonkar B, Fong P, Campbell B, Burdick JF, Boctor F. Supercritical fluid chromatography for the therapeutic drug monitoring of immunosuppressants: selectivity for cyclosporine A, FK 506 (tacrolimus), and rapamycin. J Liq Chromatogr 1994;17:2093-109.
41. Friob MC, Hassoun A, Latinne D, Lhoëst G, Otte JB, Wallemacq PE. A combined HPLC-ELISA evaluation of FK 506 in transplant patients. Transplant Proc 1991;23:2750-2.
42. Warty V, Zuckerman S, Venkataramanan R, Lever J, Fung J, Starzl T. FK506 measurement: comparison of different analytical methods. Ther Drug Monit 1993;15:204-8.
43. Warty V, Zuckerman S, Venkataramanan R, Lever J, Chao J, Mckaveney T, Fung J, Starzl T. Tacrolimus analysis: a comparison of different methods and matrices. Ther Drug Monit 1995;17:159-67.
44. Tokunaga Y, Alak AM. FK506 (tacrolimus) and its immunoreactive metabolites in whole blood of liver transplant patients and subjects with mild hepatic dysfunction. Pharm Res 1996;13:137-40.
45. Zeevi A, Eiras G, Burckart G, Jain A, Kragack A, Venkataramanan R, Todo S, Fung J, Starzl TE, Duquesnoy RJ. Bioassay of plasma specimens from liver transplant patients on FK 506 immunosuppression. Transplant Proc 1990;22:60-3.
46. Murthy JN, Chen Y, Warty VS, Venkataramanan R, Donnelly JG, Zeevi A, Soldin SJ. Radioreceptor assay for quantifying FK-506 immunosuppressant in whole blood. Clin Chem 1992;38:1307-10.
47. Asami M, Kuno T, Mukai H, Tanaka C. Detection of FK506-FKBP-calcineurin complex by a simple binding assay. Biochem Biophys Res Commun 1993;192:1388-94.