Cellular and clinical pharmacology of the taxanes docetaxel and paclitaxel -A review

Anti-Cancer Drugs

Volumn 25, Issue 5, 2014, Pages 488-494

  De Weger, Vincent A ^a   Beijnenb, Jos H ^b,c   Schellensa, Jan H M ^a,c  

^a NETHERLANDS CANCER INSTITUTE   (Netherlands)

^b SLOTERVAART HOSPITAL   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Docetaxel; P glycoprotein; P450 cytochrome; Paclitaxel; Protein binding; Taxane pharmacology

Indexed keywords

CYTOCHROME P450 2C8; CYTOCHROME P450 3A; CYTOCHROME P450 3A4; DOCETAXEL; PACLITAXEL; ANTINEOPLASTIC AGENT; TAXOID;

ANTINEOPLASTIC ACTIVITY; CANCER CHEMOTHERAPY; CLINICAL PHARMACOLOGY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG EXCRETION; DRUG FORMULATION; DRUG MECHANISM; DRUG MEGADOSE; DRUG METABOLISM; DRUG SAFETY; HUMAN; LOW DRUG DOSE; MAXIMUM TOLERATED DOSE; PHASE 1 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; REVIEW; DRUG INTERACTION; METABOLISM; METRONOMIC DRUG ADMINISTRATION; NEOPLASM;

ADMINISTRATION, METRONOMIC; ANTINEOPLASTIC AGENTS; ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; DRUG INTERACTIONS; HUMANS; MAXIMUM TOLERATED DOSE; NEOPLASMS; PACLITAXEL; TAXOIDS;

EID: 84895917442     PISSN: 09594973     EISSN: 14735741     Source Type: Journal    
DOI: 10.1097/CAD.0000000000000093     Document Type: Review

References (61)

1. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971; 93: 2325-2327.
2. Guéritte-Voegelein F, Guénard D, Lavelle F, Le Goff MT, Mangatal L, Potier P. Relationships between the structure of taxol analogues and their antimitotic activity. J Med Chem 1991; 34:992-998.
3. Weiss RB, Donehower RC, Wiernik PH, Ohnuma T, Gralla RJ, Trump DL, et al. Hypersensitivity reactions from taxol. J Clin Oncol 1990; 8: 1263-1268.
4. Nicolaou KC, Yang Z, Liu JJ, Ueno H, Nantermet PG, Guy RK, et al. Total synthesis of taxol. Nature 1994; 367:630-634.
5. Furness S, Glenny A-M, Worthington HV, Pavitt S, Oliver R, Clarkson JE, et al. Interventions for the treatment of oral cavity and oropharyngeal cancer: chemotherapy. Cochrane Database Syst Rev 2011; 4:CD006386.
6. Hickey BE, Francis DP, Lehman M. Sequencing of chemotherapy and radiotherapy for early breast cancer. Cochrane Database Syst Rev 2013; 4:CD005212.
7. Wagner AD, Unverzagt S, Grothe W, Kleber G, Grothey A, Haerting J, et al. Chemotherapy for advanced gastric cancer. Cochrane Database Syst Rev 2010; 3:CD004064.
8. Non-Small Cell Lung Cancer Collaborative group. Chemotherapy and supportive care versus supportive care alone for advanced non-small cell lung cancer. Cochrane Database Syst Rev 2010; 5:CD007309.
9. Winter-Roach BA, Kitchener HC, Lawrie TA. Adjuvant (post-surgery) chemotherapy for early stage epithelial ovarian cancer. Cochrane Database Syst Rev 2012; 3:CD004706.
10. Shelley M, Harrison C, Coles B, Staffurth J, Wilt TJ, Mason MD. Chemotherapy for hormone-refractory prostate cancer. Cochrane Database Syst Rev 2006; 4:CD005247.
11. Ringel I, Horwitz SB. Studies with RP 56976 (taxotere): a semisynthetic analogue of taxol. J Natl Cancer Inst 1991; 83:288-291.
12. Rowinsky EK. The development and clinical utility of the taxane class of antimicrotubule chemotherapy agents. Annu Rev Med 1997; 48:353-374.
13. Kerbel RS, Kamen BA. The anti-angiogenic basis of metronomic chemotherapy. Nat Rev Cancer 2004; 4:423-436.
14. Muta M, Yanagawa T, Sai Y, Saji S, Suzuki E, Aruga T, et al. Effect of lowdose paclitaxel and docetaxel on endothelial progenitor cells. Oncology 2009; 77:182-191.
15. Bocci G, Francia G, Man S, Lawler J, Kerbel RS. Thrombospondin 1, a mediator of the antiangiogenic effects of low-dose metronomic chemotherapy. Proc Natl Acad Sci USA 2003; 100:12917-12922.
16. Benelli R, Monteghirfo S, Balbi C, Barboro P, Ferrari N. Novel antivascular efficacy of metronomic docetaxel therapy in prostate cancer: hnRNP K as a player. Int J Cancer 2009; 124:2989-2996.
17. Bissery MC, Nohynek G, Sanderink GJ, Lavelle F. Docetaxel (Taxotere): a review of preclinical and clinical experience. Part I: preclinical experience. Anticancer Drugs 1995; 6:339-355, 363-368.
18. Cassier Pa, Chabaud S, Trillet-Lenoir V, Peaud P-Y, Tigaud J-D, Cure H, et al. A phase-III trial of doxorubicin and docetaxel versus doxorubicin and paclitaxel in metastatic breast cancer: results of the ERASME 3 study. Breast Cancer Res Treat 2008; 109:343-350.
19. Park SH, Lee WK, Chung M, Lee Y, Han SH, Bang S-M, et al. Paclitaxel versus docetaxel for advanced gastric cancer: a randomized phase II trial in combination with infusional 5-fluorouracil. Anticancer Drugs 2006; 17: 225-229.
20. Del Mastro L, Fabi A, Mansutti M, De Laurentiis M, Durando A, Merlo DF, et al. Randomised phase 3 open-label trial of first-line treatment with gemcitabine in association with docetaxel or paclitaxel in women with metastatic breast cancer: a comparison of different schedules and treatments. BMC Cancer 2013; 13:164.
21. Vasey PA, Jayson GC, Gordon A, Gabra H, Coleman R, Atkinson R, et al. Phase III randomized trial of docetaxel-carboplatin versus paclitaxel-carboplatin as first-line chemotherapy for ovarian carcinoma. J Natl Cancer Inst 2004; 96:1682-1691.
22. Clarke SJ, Rivory LP. Clinical pharmacokinetics of docetaxel. Clin Pharmacokinet 1999; 36:99-114.
23. Bruno R, Hille D, Riva A, Vivier N, Ten Bokkel Huinnink WW, Van Oosterom AT, et al. Population pharmacokinetics/pharmacodynamics of docetaxel in phase II studies in patients with cancer. J Clin Oncol 1998; 16:187-196.
24. Di Maio M, Perrone F, Chiodini P, Gallo C, Camps C, Schuette W, et al. Individual patient data meta-analysis of docetaxel administered once every 3 weeks compared with once every week second-line treatment of advanced non-small-cell lung cancer. J Clin Oncol 2007; 25:1377-1382.
25. Eisenhauer EA, Ten Bokkel Huinink WW, Swenerton KD, Gianni L, Myles J, Van der Burg ME, et al. European-Canadian randomized trial of paclitaxel in relapsed ovarian cancer: high-dose versus low-dose and long versus short infusion. J Clin Oncol 1994; 12:2654-2666.
26. Gelderblom H, Verweij J, Nooter K, Sparreboom A. Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur J Cancer 2001; 37:1590-1598.
27. Huizing MT, Keung AC, Rosing H, Van der Kuij V, Ten Bokkel Huinink WW, Mandjes IM, et al. Pharmacokinetics of paclitaxel and metabolites in a randomized comparative study in platinum-pretreated ovarian cancer patients. J Clin Oncol 1993; 11:2127-2135.
28. Kearns CM, Gianni L, Egorin MJ. Paclitaxel pharmacokinetics and pharmacodynamics. Semin Oncol 1995; 22:16-23.
29. Van Oosterom AT, Schrijvers D, Schriivers D. Docetaxel (Taxotere), a review of preclinical and clinical experience. Part II: clinical experience. Anticancer Drugs 1995; 6:356-368.
30. Wu H, Xin Y, Zhao J, Sun D, Li W, Hu Y, et al. Metronomic docetaxel chemotherapy inhibits angiogenesis and tumor growth in a gastric cancer model. Cancer Chemother Pharmacol 2011; 68:879-887.
31. Ng SSW, Sparreboom A, Shaked Y, Lee C, Man S, Desai N, et al. Influence of formulation vehicle on metronomic taxane chemotherapy: albumin-bound versus cremophor EL-based paclitaxel. Clin Cancer Res 2006; 12: 4331-4338.
32. Vacca A, Ribatti D, Iurlaro M, Merchionne F, Nico B, Ria R, et al. Docetaxel versus paclitaxel for antiangiogenesis. J Hematother Stem Cell Res 2002; 11:103-118.
33. Bhatt RS, Merchan J, Parker R, Wu H-K, Zhang L, Seery V, et al. A phase 2 pilot trial of low-dose, continuous infusion, or ''metronomic'' paclitaxel and oral celecoxib in patients with metastatic melanoma. Cancer 2010; 116:1751-1756.
34. Moes J, Koolen S, Huitema A, Schellens J, Beijnen J, Nuijen B. Development of an oral solid dispersion formulation for use in low-dose metronomic chemotherapy of paclitaxel. Eur J Pharm Biopharm 2013; 83:87-94.
35. Lian H, Zhang T, Sun J, Liu X, Ren G, Kou L, et al. Enhanced oral delivery of paclitaxel using acetylcysteine functionalized chitosan-vitamin E succinate nanomicelles based on a mucus bioadhesion and penetration mechanism. Mol Pharmaceutics 2013; 10:3447-3458.
36. Sparreboom A, Van Tellingen O, Nooijen WJ, Beijnen JH. Preclinical pharmacokinetics of paclitaxel and docetaxel. Anticancer Drugs 1998; 9:1-17.
37. Eiseman JL, Eddington ND, Leslie J, MacAuley C, Sentz DL, Zuhowski M, et al. Plasma pharmacokinetics and tissue distribution of paclitaxel in CD2F1 mice. Cancer Chemother Pharmacol 1994; 34:465-471.
38. Sparreboom A, Van Asperen J, Van Tellingen O. Pharmacokinetics of paclitaxel in mdr1a P-glycoprotein deficient mice after intravenous and oral administration [Abstract]. Ann Oncol 1996; 7.
39. Fujita H, Okamoto M, Takao A, Mase H, Kojima H. Pharmacokinetics of paclitaxel in experimental animals. Part 2. Tissue distribution. Gan To Kagaku Ryoho 1994; 21:659-664.
40. Sparreboom A, Van Asperen J, Mayer U, Schinkel AH, Smit JW, Meijer DK, et al. Limited oral bioavailability and active epithelial excretion of paclitaxel (Taxol) caused by P-glycoprotein in the intestine. Proc Natl Acad Sci USA 1997; 94:2031-2035.
41. Bardelmeijer HA, Ouwehand M, Buckle T, Huisman MT, Schellens JHM, Beijnen JH, et al. Low systemic exposure of oral docetaxel in mice resulting from extensive first-pass metabolism is boosted by ritonavir. Cancer Res 2002; 62:6158-6164.
42. Lagas JS, Vlaming ML, Van Tellingen O, Wagenaar E, Jansen RS, Rosing H, et al. Multidrug resistance protein 2 is an important determinant of paclitaxel pharmacokinetics. Clin Cancer Res 2006; 12:6125-6132.
43. Huisman MT, Chhatta AA, Van Tellingen O, Beijnen JH, Schinkel AH. MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer 2005; 116:824-829.
44. Hendrikx JJMA, Lagas JS, Rosing H, Schellens JHM, Beijnen JH, Schinkel AH. P-glycoprotein and cytochrome P450 3A act together in restricting the oral bioavailability of paclitaxel. Int J Cancer 2013; 132:2439-2447.
45. Malingré MM, Terwogt JM, Beijnen JH, Rosing H, Koopman FJ, Van Tellingen O, et al. Phase I and pharmacokinetic study of oral paclitaxel. J Clin Oncol 2000; 18:2468-2475.
46. Rahman A, Korzekwa KR, Grogan J, Gonzalez FJ, Harris JW. Selective biotransformation of taxol to 6 alpha-hydroxytaxol by human cytochrome P450 2C8. Cancer Res 1994; 54:5543-5546.
47. Cresteil T, Monsarrat B, Dubois J, Sonnier M, Alvinerie P, Gueritte F. Regioselective metabolism of taxoids by human CYP3A4 and 2C8: structure-activity relationship. Drug Metab Dispos 2002; 30:438-445.
48. Sparreboom A, Huizing MT, Boesen JJ, Nooijen WJ, Van Tellingen O, Beijnen JH. Isolation, purification, and biological activity of mono- and dihydroxylated paclitaxel metabolites from human feces. Cancer Chemother Pharmacol 1995; 36:299-304.
49. Sparreboom A, Van Tellingen O, Nooijen WJ, Beijnen JH. Tissue distribution, metabolism and excretion of paclitaxel in mice. Anticancer Drugs 1996; 7:78-86.
50. Royer I, Monsarrat B, Sonnier M, Wright M, Cresteil T. Metabolism of docetaxel by human cytochromes P450: interactions with paclitaxel and other antineoplastic drugs. Cancer Res 1996; 56:58-65.
51. Harris JW, Katki A, Anderson LW, Chmurny GN, Paukstelis JV, Collins JM. Isolation, structural determination, and biological activity of 6 alphahydroxytaxol, the principal human metabolite of taxol. J Med Chem 1994; 37:706-709.
52. Sparreboom A, Van Tellingen O, Scherrenburg EJ, Boesen JJ, Huizing MT, Nooijen WJ, et al. Isolation, purification and biological activity of major docetaxel metabolites from human feces. Drug Metab Dispos 1996; 24:655-658.
53. Van Waterschoot RAB, Lagas JS, Wagenaar E, Rosing H, Beijnen JH, Schinkel AH. Individual and combined roles of CYP3A, P-glycoprotein (MDR1/ABCB1) and MRP2 (ABCC2) in the pharmacokinetics of docetaxel. Int J Cancer 2010; 127:2959-2964.
54. Cresteil T, Monsarrat B, Alvinerie P, Tréluyer JM, Vieira I, Wright M. Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involved in its biotransformation. Cancer Res 1994; 54:386-392.
55. Roy V, LaPlant BR, Gross GG, Bane CL, Palmieri FM. Phase II trial of weekly nab (nanoparticle albumin-bound)-paclitaxel (nab-paclitaxel) (Abraxane) in combination with gemcitabine in patients with metastatic breast cancer (N0531). Ann Oncol 2009; 20:449-453.
56. Blum JL, Savin MA, Edelman G, Pippen JE, Robert NJ, Geister BV, et al. Phase II study of weekly albumin-bound paclitaxel for patients with metastatic breast cancer heavily pretreated with taxanes. Clin Breast Cancer 2007; 7:850-856.
57. Hosein PJ, De Lima Lopes G, Pastorini VH, Gomez C, Macintyre J, Zayas G, et al. A phase II trial of nab-paclitaxel as second-line therapy in patients with advanced pancreatic cancer. Am J Clin Oncol 2013; 36:151-156.
58. Ho C, Davies AM, Sangha RS, Lau D, Lara P, Chew HK, et al. Phase I/II trial of pemetrexed plus nab-paclitaxel in advanced solid tumor patients with emphasis on non-small cell lung cancer. Invest New Drugs 2013; 31: 1587-1591.
59. Moes JJ, Stuurman FE, Hendrikx JJMA, Marchetti S, Huitema ADR, Beijnen JH, et al. Pharmacokinetic evaluation of three oral formulations of docetaxel boosted with ritonavir: two single-drug formulations vs. a fixed-dose combination tablet. Drug Deliv Transl Res 2013; 3:243-251.
60. Marchetti S, Stuurman F, Koolen S, Moes J, Hendrikx J, Thijssen B, et al. Phase I study of weekly oral docetaxel (ModraDoc001) plus ritonavir in patients with advanced solid tumors. ASCO annual meeting, 2012. [Abstract 2550].
61. Baker SD, Zhao M, Lee CKK, Verweij J, Zabelina Y, Brahmer JR, et al. Comparative pharmacokinetics of weekly and every-three-weeks docetaxel. Clin Cancer Res 2004; 10:1976-1983.