Factors affecting the in vivo lactone stability and systemic clearance of the lipophilic camptothecin analogue AR-67

Pharmaceutical Research

Volumn 27, Issue 7, 2010, Pages 1416-1425

  Adane, Eyob D ^a   Liu, Zhiwei ^a   Xiang, Tian Xiang ^a   Anderson, Bradley D ^a   Leggas, Markos ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

BCRP; Carboxylate; Lactone; OATP Oatp; P gp

Indexed keywords

AR 67; CAMPTOTHECIN; CARBOXYLIC ACID; DB 67; ELACRIDAR; LACTONE; RIFAMPICIN; UNCLASSIFIED DRUG; 7-TERT-BUTYLDIMETHYLSILYL-10-HYDROXYCAMPTOTHECIN; ORGANOSILICON DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG CONFORMATION; DRUG DISPOSITION; DRUG STABILITY; DRUG STRUCTURE; FEMALE; IN VIVO STUDY; LIPOPHILICITY; NONHUMAN; PHARMACOLOGICAL BLOCKING; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SYSTEMIC THERAPY; ANALOGS AND DERIVATIVES; ANIMAL; BIOLOGICAL MODEL; BLOOD; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPRAGUE DAWLEY RAT;

ANIMALS; CAMPTOTHECIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; FEMALE; LACTONES; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 77953613486     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-010-0137-3     Document Type: Article

References (36)

1. D Bom DP Curran S Kruszewski SG Zimmer J Thompson Strode G Kohlhagen, et al. 2000 The novel silatecan 7-tert-butyldimethylsilyl-10-hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity J Med Chem. 43 3970 80 10.1021/jm000144o 1:CAS:528:DC%2BD3cXmsFeitL0%3D 11052802
2. IF Pollack M Erff D Bom TG Burke JT Strode DP Curran 1999 Potent topoisomerase I inhibition by novel silatecans eliminates glioma proliferation in vitro and in vivo Cancer Res. 59 4898 905 1:CAS:528:DyaK1MXmslWktLg%3D 10519402
3. SM Arnold JJ Rinehart E Tsakalozou JR Eckardt SZ Fields BJ Shelton, et al. 2010 A phase I study of 7-t-butyldimethylsilyl-10-hydroxycamptothecin in adult patients with refractory or metastatic solid malignancies Clin Cancer Res. 16 673 80 10.1158/1078-0432.CCR-09-2429 1:CAS:528:DC%2BC3cXktF2qt7c%3D 20068096
4. J Fassberg VJ Stella 1992 A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues J Pharm Sci. 81 676 84 10.1002/jps.2600810718 1:CAS:528:DyaK3sXjvFagtg%3D%3D 1403703 (Pubitemid 23006796)
5. C Jaxel KW Kohn MC Wani ME Wall Y Pommier 1989 Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity Cancer Res. 49 1465 9 1:CAS:528:DyaL1MXitVGjtLs%3D 2538227
6. YH Hsiang LF Liu 1988 Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin Cancer Res. 48 1722 6 1:CAS:528:DyaL1cXhsl2ks7Y%3D 2832051
7. TG Burke Z Mi 1993 Preferential binding of the carboxylate form of camptothecin by human serum albumin Anal Biochem. 212 285 7 10.1006/abio.1993. 1325 1:CAS:528:DyaK3sXltlWjurY%3D 8368506 (Pubitemid 23219487)
8. JG Liehr AE Ahmed BC Giovanella 1996 Pharmacokinetics of camptothecins administered orally Ann N Y Acad Sci. 803 157 63 10.1111/j.1749-6632.1996. tb26384.x 1:CAS:528:DyaK2sXhtV2htL8%3D 8993508 (Pubitemid 27057982)
9. PJ Creaven LM Allen FM Muggia 1972 Plasma camptothecin (NSC-100880) levels during a 5-day course of treatment: relation to dose and toxicity Cancer Chemother Rep. 56 573 8 1:STN:280:DyaE3s7itFentA%3D%3D 4652588
10. EA Natelson BC Giovanella CF Verschraegen KM Fehir PD De Ipolyi N Harris, et al. 1996 Phase I clinical and pharmacological studies of 20-(S)-camptothecin and 20-(S)-9-nitrocamptothecin as anticancer agents Ann N Y Acad Sci. 803 224 30 10.1111/j.1749-6632.1996.tb26392.x 1:CAS:528:DyaK2sXhtV2htLc%3D 8993516 (Pubitemid 27057990)
11. AK Lalloo FR Luo A Guo PV Paranjpe SH Lee V Vyas, et al. 2004 Membrane transport of camptothecin: facilitation by human P-glycoprotein (ABCB1) and multidrug resistance protein 2 (ABCC2) BMC Med. 2 16 10.1186/1741-7015-2-16 15125776 (Pubitemid 39111862)
12. T Nozawa H Minami S Sugiura A Tsuji I Tamai 2005 Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite, 7-ethyl-10-hydroxycamptothecin: in vitro evidence and effect of single nucleotide polymorphisms Drug Metab Dispos. 33 434 9 10.1124/dmd.104. 001909 1:CAS:528:DC%2BD2MXisFSgtrk%3D 15608127 (Pubitemid 40279945)
13. S Marchetti RL Oostendorp D Pluim M van Eijndhoven O van Tellingen AH Schinkel, et al. 2007 In vitro transport of gimatecan (7-t- butoxyiminomethylcamptothecin) by breast cancer resistance protein, P-glycoprotein, and multidrug resistance protein 2 Mol Cancer Ther. 6 3307 13 10.1158/1535-7163.MCT-07-0461 1:CAS:528:DC%2BD2sXhsVCjsrrK 18089724
14. H Li HE Jin W Kim YH Han DD Kim SJ Chung, et al. 2008 Involvement of P-glycoprotein, multidrug resistance protein 2 and breast cancer resistance protein in the transport of belotecan and topotecan in Caco-2 and MDCKII cells Pharm Res. 25 2601 12 10.1007/s11095-008-9678-0 1:CAS:528:DC%2BD1cXht1aisb7J 18654741
15. Adane ED, Monks N, Roberts MJ, Horn J, Moscow JA, Leggas M. Transporter Pathways for the Novel Camptothecin Analog DB-67. AAPS Abstract M1032, AAPS Workshop on Drug Transporters in ADME: From the Bench to the Bedside (2007).
16. DO Scott DS Bindra VJ Stella 1993 Plasma pharmacokinetics of lactone and carboxylate forms of 20(S)-camptothecin in anesthetized rats Pharm Res. 10 1451 7 10.1023/A:1018919224450 1:CAS:528:DyaK2cXhtFA%3D 8272406 (Pubitemid 23302661)
17. DO Scott DS Bindra SC Sutton VJ Stella 1994 Urinary and biliary disposition of the lactone and carboxylate forms of 20(S)-camptothecin in rats Drug Metab Dispos. 22 438 42 1:CAS:528:DyaK2cXkt1Khsrg%3D 8070321
18. BE Davies EA Minthorn MJ Dennis H Rosing JH Beijnen 1997 The pharmacokinetics of topotecan and its carboxylate form following separate intravenous administration to the dog Pharm Res. 14 1461 5 10.1023/A: 1012189225880 1:CAS:528:DyaK2sXntFehtL8%3D 9358562 (Pubitemid 27481080)
19. LP Rivory E Chatelut P Canal A Mathieu-Boue J Robert 1994 Kinetics of the in vivo interconversion of the carboxylate and lactone forms of irinotecan (CPT-11) and of its metabolite SN-38 in patients Cancer Res. 54 6330 3 1:CAS:528:DyaK2MXislamu70%3D 7987823
20. WF Ebling WJ Jusko 1986 The determination of essential clearance, volume, and residence time parameters of recirculating metabolic systems: the reversible metabolism of methylprednisolone and methylprednisone in rabbits J Pharmacokinet Biopharm. 14 557 99 10.1007/BF01067965 1:CAS:528: DyaL2sXps1ejtQ%3D%3D 3820091
21. HY Cheng WJ Jusko 1991 Mean residence times and distribution volumes for drugs undergoing linear reversible metabolism and tissue distribution and linear or nonlinear elimination from the central compartments Pharm Res. 8 508 11 10.1023/A:1015811514050 1:CAS:528:DyaK3MXit1SksLw%3D 1871048
22. J Horn SL Jordan L Song MJ Roberts BD Anderson M Leggas 2006 Validation of an HPLC method for analysis of DB-67 and its water soluble prodrug in mouse plasma J Chromatogr B Analyt Technol Biomed Life Sci. 844 15 22 10.1016/j.jchromb.2006.06.022 1:CAS:528:DC%2BD28Xht1SjsrfJ 16860004 (Pubitemid 46048600)
23. D'Argenio DZ, Schumitzky A. ADAPT II User's Guide: Pharmacokinetic/ Pharmacodynamic Systems Analysis Software. Biomedical Simulations Resource (1997).
24. H Cheng WJ Jusko 1993 Pharmacokinetics of reversible metabolic systems Biopharm Drug Dispos. 14 721 66 10.1002/bdd.2510140902 1:CAS:528: DyaK2cXpsVClsQ%3D%3D 8298069 (Pubitemid 23351420)
25. Rowland M, Tozer TN. Clinical Pharmacokinetics: Concents and Applications, Williams & Wilkins (1995).
26. Z Mi TG Burke 1994 Differential interactions of camptothecin lactone and carboxylate forms with human blood components Biochemistry 33 10325 36 10.1021/bi00200a013 1:CAS:528:DyaK2cXlsVynurc%3D 8068669
27. JW Jonker JW Smit RF Brinkhuis M Maliepaard JH Beijnen JH Schellens, et al. 2000 Role of breast cancer resistance protein in the bioavailability and fetal penetration of topotecan J Natl Cancer Inst. 92 1651 6 10.1093/jnci/92.20.1651 1:CAS:528:DC%2BD3cXnvV2mtbw%3D 11036110
28. CM Kruijtzer JH Beijnen H Rosing WW ten Bokkel Huinink M Schot RC Jewell, et al. 2002 Increased oral bioavailability of topotecan in combination with the breast cancer resistance protein and P-glycoprotein inhibitor GF120918 J Clin Oncol. 20 2943 50 10.1200/JCO.2002.12.116 1:CAS:528:DC%2BD38Xlslyrt7w%3D 12089223 (Pubitemid 34728888)
29. IE Kuppens EO Witteveen RC Jewell SA Radema EM Paul SG Mangum, et al. 2007 A phase I, randomized, open-label, parallel-cohort, dose-finding study of elacridar (GF120918) and oral topotecan in cancer patients Clin Cancer Res. 13 3276 85 10.1158/1078-0432.CCR-06-2414 1:CAS:528:DC%2BD2sXmtVaju70%3D 17545533 (Pubitemid 46944913)
30. RL Oostendorp E van de Steeg CM van der Kruijssen JH Beijnen KE Kenworthy AH Schinkel, et al. 2009 Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors Drug Metab Dispos. 37 917 23 10.1124/dmd.108.024901 1:CAS:528:DC%2BD1MXktVSrs78%3D 19139163
31. YY Lau H Okochi Y Huang LZ Benet 2006 Pharmacokinetics of atorvastatin and its hydroxy metabolites in rats and the effects of concomitant rifampicin single doses: relevance of first-pass effect from hepatic uptake transporters, and intestinal and hepatic metabolism Drug Metab Dispos. 34 1175 81 10.1124/dmd.105.009076 1:CAS:528:DC%2BD28XmsVKqsLo%3D 16624870
32. J Zong GM Pollack 2003 Modulation of P-glycoprotein transport activity in the mouse blood-brain barrier by rifampin J Pharmacol Exp Ther. 306 556 62 10.1124/jpet.103.049452 1:CAS:528:DC%2BD3sXlslGltbs%3D 12721332 (Pubitemid 36886154)
33. A Sparreboom H Gelderblom S Marsh R Ahluwalia R Obach P Principe, et al. 2004 Diflomotecan pharmacokinetics in relation to ABCG2 421C>A genotype Clin Pharmacol Ther. 76 38 44 10.1016/j.clpt.2004.03.003 1:CAS:528: DC%2BD2cXlsVaqtrs%3D 15229462 (Pubitemid 38844732)
34. M Niemi E Schaeffeler T Lang MF Fromm M Neuvonen C Kyrklund, et al. 2004 High plasma pravastatin concentrations are associated with single nucleotide polymorphisms and haplotypes of organic anion transporting polypeptide-C (OATP-C, SLCO1B1) Pharmacogenetics 14 429 40 10.1097/01.fpc.0000114750.08559.32 1:CAS:528:DC%2BD2cXlt1Cktrk%3D 15226675 (Pubitemid 38971233)
35. YY Lau Y Huang L Frassetto LZ Benet 2007 effect of OATP1B transporter inhibition on the pharmacokinetics of atorvastatin in healthy volunteers Clin Pharmacol Ther. 81 194 204 10.1038/sj.clpt.6100038 1:CAS:528: DC%2BD2sXisFyrtLY%3D 17192770 (Pubitemid 46174816)
36. YY Lau H Okochi Y Huang LZ Benet 2006 Multiple transporters affect the disposition of atorvastatin and its two active hydroxy metabolites: application of in vitro and ex situ systems J Pharmacol Exp Ther. 316 762 71 10.1124/jpet.105.093088 1:CAS:528:DC%2BD28XhtlWqtrg%3D 16258024 (Pubitemid 43131004)