The transfer of 6-mercaptopurine in the dually perfused human placenta

Reproductive Toxicology

Volumn 32, Issue 3, 2011, Pages 349-353

  Hutson, J R ^a,b   Lubetsky, A ^a   Walfisch, A ^a   Ballios, B G ^b   Garcia Bournissen, F ^a,b   Koren, G ^a,b  

^a HOSPITAL FOR SICK CHILDREN   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

6 Mercaptopurine; Azathioprine; Placenta; Placental perfusion; Pregnancy

Indexed keywords

MERCAPTOPURINE;

ACTIVE TRANSPORT; ARTICLE; CONTROLLED STUDY; DRUG TRANSPORT; FEMALE; FETUS CIRCULATION; HUMAN; HUMAN TISSUE; PLACENTA PERFUSION; PLACENTAL TRANSFER;

6-MERCAPTOPURINE; ANTIPYRINE; FEMALE; HUMANS; MATERNAL-FETAL EXCHANGE; PERFUSION; PLACENTA; PREGNANCY;

EID: 80755132251     PISSN: 08906238     EISSN: 18731708     Source Type: Journal    
DOI: 10.1016/j.reprotox.2011.08.008     Document Type: Article

References (38)

1. Goldstein L.H., Dolinsky G., Greenberg R., Schaefer C., Cohen-Kerem R., Diav-Citrin O., et al. Pregnancy outcome of women exposed to azathioprine during pregnancy. Birth Defects Res A Clin Mol Teratol 2007, 79:696-701.
2. Cooper G.S., Stroehla B.C. The epidemiology of autoimmune diseases. Autoimmun Rev 2003, 2:119-125.
3. Polifka J.E., Friedman J.M. Teratogen update: azathioprine and 6-mercaptopurine. Teratology 2002, 65:240-261.
4. Francella A., Dyan A., Bodian C., Rubin P., Chapman M., Present D.H. The safety of 6-mercaptopurine for childbearing patients with inflammatory bowel disease: a retrospective cohort study. Gastroenterology 2003, 124:9-17.
5. Coelho J., Beaugerie L., Colombel J.F., Hebuterne X., Lerebours E., Lemann M., et al. Pregnancy outcome in patients with inflammatory bowel disease treated with thiopurines: cohort from the CESAME study. Gut 2011, 60:198-203.
6. Cleary B.J., Kallen B. Early pregnancy azathioprine use and pregnancy outcomes. Birth Defects Res A Clin Mol Teratol 2009, 85:647-654.
7. Mountifield R.E., Prosser R., Bampton P., Muller K., Andrews J.M. Pregnancy and IBD treatment: this challenging interplay from a patients' perspective. J Crohns Colitis 2010, 4:176-182.
8. Peyrin-Biroulet L., Oussalah A., Roblin X., Sparrow M.P. The use of azathioprine in Crohn's disease during pregnancy and in the post-operative setting: a worldwide survey of experts. Aliment Pharmacol Ther 2011, 33:707-713.
9. Davis A.R., Miller L., Tamimi H., Gown A. Methotrexate compared with mercaptopurine for early induced abortion. Obstet Gynecol 1999, 93:904-909.
10. Saarikoski S., Seppala M. Immunosuppression during pregnancy: transmission of azathioprine and its metabolites from the mother to the fetus. Am J Obstet Gynecol 1973, 115:1100-1106.
11. de Boer N.K., Jarbandhan S.V., de Graaf P., Mulder C.J., van Elburg R.M., van Bodegraven A.A. Azathioprine use during pregnancy: unexpected intrauterine exposure to metabolites. Am J Gastroenterol 2006, 101:1390-1392.
12. de Wolf C., Jansen R., Yamaguchi H., de Haas M., van de Wetering K., Wijnholds J., et al. Contribution of the drug transporter ABCG2 (breast cancer resistance protein) to resistance against anticancer nucleosides. Mol Cancer Ther 2008, 7:3092-3102.
13. Maliepaard M., Scheffer G.L., Faneyte I.F., van Gastelen M.A., Pijnenborg A.C., Schinkel A.H., et al. Subcellular localization and distribution of the breast cancer resistance protein transporter in normal human tissues. Cancer Res 2001, 61:3458-3464.
14. Jonker J.W., Smit J.W., Brinkhuis R.F., Maliepaard M., Beijnen J.H., Schellens J.H., et al. Role of breast cancer resistance protein in the bioavailability and fetal penetration of topotecan. J Natl Cancer Inst 2000, 92:1651-1656.
15. Pollex E., Lubetsky A., Koren G. The role of placental breast cancer resistance protein in the efflux of glyburide across the human placenta. Placenta 2008, 29:743-747.
16. Miller R.K., Wier P.J., Maulik D., di Sant'Agnese P.A. Human placenta in vitro: characterization during 12h of dual perfusion. Contrib Gynecol Obstet 1985, 13:77-84.
17. Derewlany L.O., Leeder J.S., Kumar R., Radde I.C., Knie B., Koren G. The transport of digoxin across the perfused human placental lobule. J Pharmacol Exp Ther 1991, 256:1107-1111.
18. Reynolds F., Knott C. Pharmacokinetics in pregnancy and placental drug transfer. Oxf Rev Reprod Biol 1989, 11:389-449.
19. Bergan S., Rugstad H.E., Bentdal O., Endresen L., Stokke O. Kinetics of mercaptopurine and thioguanine nucleotides in renal transplant recipients during azathioprine treatment. Ther Drug Monit 1994, 16:13-20.
20. Zins B.J., Sandborn W.J., McKinney J.A., Mays D.C., van Os E.C., Tremaine W.J., et al. A dose-ranging study of azathioprine pharmacokinetics after single-dose administration of a delayed-release oral formulation. J Clin Pharmacol 1997, 37:38-46.
21. Lennard L., Singleton H.J. High-performance liquid chromatographic assay of the methyl and nucleotide metabolites of 6-mercaptopurine: quantitation of red blood cell 6-thioguanine nucleotide, 6-thioinosinic acid and 6-methylmercaptopurine metabolites in a single sample. J Chromatogr 1992, 583:83-90.
22. Hawwa A.F., Millership J.S., Collier P.S., McElnay J.C. Development and validation of an HPLC method for the rapid and simultaneous determination of 6-mercaptopurine and four of its metabolites in plasma and red blood cells. J Pharm Biomed Anal 2009, 49:401-409.
23. 6-Mercaptopurine (Monograph #05871). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals 2010, Merck & Co., Inc., Whitehouse Station, NJ, USA. M. O'Neil, P. Heckelman, C. Koch, K. Roman (Eds.).
24. de Boer N.K., Van Elburg R.M., Wilhelm A.J., Remmink A.J., Van Vugt J.M., Mulder C.J., et al. 6-Thioguanine for Crohn's disease during pregnancy: thiopurine metabolite measurements in both mother and child. Scand J Gastroenterol 2005, 40:1374-1377.
25. Kraemer J., Klein J., Lubetsky A., Koren G. Perfusion studies of glyburide transfer across the human placenta: implications for fetal safety. Am J Obstet Gynecol 2006, 195:270-274.
26. Govindarajan R., Bakken A.H., Hudkins K.L., Lai Y., Casado F.J., Pastor-Anglada M., et al. In situ hybridization and immunolocalization of concentrative and equilibrative nucleoside transporters in the human intestine, liver, kidneys, and placenta. Am J Physiol Regul Integr Comp Physiol 2007, 293:R1809-R1822.
27. Nagai K., Nagasawa K., Kihara Y., Okuda H., Fujimoto S. Anticancer nucleobase analogues 6-mercaptopurine and 6-thioguanine are novel substrates for equilibrative nucleoside transporter 2. Int J Pharm 2007, 333:56-61.
28. Ganapathy V., Prasad P.D., Ganapathy M.E., Leibach F.H. Placental transporters relevant to drug distribution across the maternal-fetal interface. J Pharmacol Exp Ther 2000, 294:413-420.
29. Wijnholds J., Mol C.A., van Deemter L., de Haas M., Scheffer G.L., Baas F., et al. Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A 2000, 97:7476-7481.
30. Wielinga P.R., Reid G., Challa E.E., van der Heijden I., van Deemter L., de Haas M., et al. Thiopurine metabolism and identification of the thiopurine metabolites transported by MRP4 and MRP5 overexpressed in human embryonic kidney cells. Mol Pharmacol 2002, 62:1321-1331.
31. Meyer Zu Schwabedissen H.E., Grube M., Heydrich B., Linnemann K., Fusch C., Kroemer H.K., et al. Expression, localization, and function of MRP5 (ABCC5), a transporter for cyclic nucleotides, in human placenta and cultured human trophoblasts: effects of gestational age and cellular differentiation. Am J Pathol 2005, 166:39-48.
32. Myllynen P., Pienimaki P., Vahakangas K. Human placental perfusion method in the assessment of transplacental passage of antiepileptic drugs. Toxicol Appl Pharmacol 2005, 207:489-494.
33. Hutson J.R., Garcia-Bournissen F., Davis A., Koren G. Estimating fetal drug exposure using the human placental perfusion model: a systematic review and development of a model to predict in vivo transfer. Clin Pharmacol Ther 2011, 90:67-76.
34. Chan G.L., Canafax D.M., Johnson C.A. The therapeutic use of azathioprine in renal transplantation. Pharmacotherapy 1987, 7:165-177.
35. Ohlman S., Albertioni F., Peterson C. Day-to-day variability in azathioprine pharmacokinetics in renal transplant recipients. Clin Transplant 1994, 8:217-223.
36. de Graaf P., Vos R.M., de Boer N.H., Sinjewel A., Jharap B., Mulder C.J., et al. Limited stability of thiopurine metabolites in blood samples: Relevant in research and clinical practise. J Chromatogr B Analyt Technol Biomed Life Sci 2010, 878:1437-1442.
37. Kwan L.Y., Mahadevan U. Inflammatory bowel disease and pregnancy: an update. Expert Rev Clin Immunol 2010, 6:643-657.
38. Sahasranaman S., Howard D., Roy S. Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol 2008, 64:753-767.