Pharmacokinetic evaluation of vadimezan (ASA404, 5,6-dimethylxanthenone-4- acetic acid, DMXAA)

Expert Opinion on Drug Metabolism and Toxicology

Volumn 7, Issue 10, 2011, Pages 1315-1326

  Jameson, Michael B ^a   Head, Michelle ^b  

^a WAIKATO HOSPITAL   (New Zealand)

^b WELLINGTON HOSPITAL   (New Zealand)

Author keywords

5,6 dimethylxanthenone 4 acetic acid; ASA404; Pharmacokinetics; Vadimezan; Vascular disrupting agent

Indexed keywords

CAFFEINE; CARBOPLATIN; CETUXIMAB; CISPLATIN; CYCLOPHOSPHAMIDE; CYPROHEPTADINE; CYTOCHROME P450 1A2; DAUNORUBICIN; DICLOFENAC; DOCETAXEL; FLUOROURACIL; FLUVOXAMINE; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; IRINOTECAN; MELPHALAN; METHOTREXATE; OMEPRAZOLE; PACLITAXEL; SIMVASTATIN; TAXANE DERIVATIVE; THALIDOMIDE; TIRAPAZAMINE; TROPONIN I; VADIMEZAN; VINCA ALKALOID;

ANGINA PECTORIS; ANTINEOPLASTIC ACTIVITY; ANXIETY; AREA UNDER THE CURVE; BINDING AFFINITY; BINDING SITE; BLOOD PRESSURE VARIABILITY; CANCER SURVIVAL; CARDIOMYOPATHY; CARDIOTOXICITY; CONFUSION; CYTOTOXICITY; DOSE RESPONSE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG DOSE COMPARISON; DRUG DOSE ESCALATION; DRUG EFFICACY; DRUG ELIMINATION; DRUG EXCRETION; DRUG GLUCURONIDATION; DRUG HYDROXYLATION; DRUG HYPERSENSITIVITY; DRUG INFUSION; DRUG METABOLISM; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG SAFETY; DRUG SCREENING; DRUG TOLERABILITY; DRUG TRANSPORT; DYSGEUSIA; EX VIVO STUDY; FEBRILE NEUTROPENIA; HEART ARRHYTHMIA; HEART LEFT VENTRICLE FAILURE; HEART MUSCLE ISCHEMIA; HEART RATE VARIABILITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INFECTION; INNATE IMMUNITY; ISOLATED LIVER; KIDNEY MICROSOME; LETHAL DOSE; LIVER MICROSOME; LUNG NON SMALL CELL CANCER; LUNG SMALL CELL CANCER; MAXIMUM TOLERATED DOSE; MELANOMA; MULTIPLE CYCLE TREATMENT; NAUSEA AND VOMITING; NEUTROPENIA; NONHUMAN; OVARY CANCER; PHARMACOKINETICS; PROSTATE CANCER; QT PROLONGATION; REVIEW; SINGLE DRUG DOSE; SLURRED SPEECH; SQUAMOUS CELL CARCINOMA; STEADY STATE; SWEATING; TACHYCARDIA; THROMBOCYTOPENIA; TRANSITIONAL CELL CARCINOMA; TREATMENT RESPONSE; TREMOR; TUMOR BLOOD FLOW; TUMOR IMMUNITY; UNSPECIFIED SIDE EFFECT; URINE INCONTINENCE; URINE RETENTION; UTERINE CERVIX CARCINOMA; VISUAL DISORDER;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; CLINICAL TRIALS, PHASE I AS TOPIC; CLINICAL TRIALS, PHASE II AS TOPIC; CLINICAL TRIALS, PHASE III AS TOPIC; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION; HUMANS; NEOPLASMS; RANDOMIZED CONTROLLED TRIALS AS TOPIC; XANTHONES;

EID: 80053038907     PISSN: 17425255     EISSN: 17447607     Source Type: Journal    
DOI: 10.1517/17425255.2011.614389     Document Type: Review

References (58)

1. Denekamp J. Vascular endothelium as the vulnerable element in tumours. Acta Radiol Oncol 1984;7:217-25 (Pubitemid 15072794)
2. Konerding MA, Malkusch W, Klapthor B, et al. Evidence for characteristic vascular patterns in solid tumours: quantitative studies using corrosion casts. Br J Cancer 1999;80:724-32 (Pubitemid 29209835)
3. Folkman J. Tumor angiogenesis: therapeutic implications. N Engl J Med 1971;285:1182-6
4. Siemann DW, Chaplin DJ, Horsman MR. Vascular-targeting therapies for treatment of malignant disease. Cancer 2004;100:2491-9 (Pubitemid 38715753)
5. Lippert JW III. Vascular disrupting agents. Bioorg Med Chem 2007;15:605-15
6. Ching LM, Zwain S, Baguley BC. Relationship between tumour endothelial cell apoptosis and tumour blood flow shutdown following treatment with the antivascular agent DMXAA in mice. Br J Cancer 2004;90:906-10 (Pubitemid 38406605)
7. Kestell P, Zhao L, Jameson MB, et al. Measurement of plasma 5-hydroxyindoleacetic acid as a possible clinical surrogate marker for the action of antivascular agents. Clin Chim Acta 2001;314:159-66 (Pubitemid 33079194)
8. Kelland LR, Baguley BC, Zhao L, et al. Plasma levels of 5-hydroxyindole-3-acetic acid (5HIAA) as a pharmacodynamic marker of blood flow changes induced by the vascular targeting agent (VTA) 5,6 dimethyl xanthenone acetic acid, DMXAA. Proc Annu Meet Am Soc Clin Oncol 2005;24:#3123
9. Baguley BC, Siemann DW. Temporal aspects of the action of ASA404 (vadimezan; DMXAA). Expert Opin Investig Drugs 2010;19:1413-25
10. Siim BG, Lee AE, Shalal-Zwain S, et al. Marked potentiation of the antitumour activity of chemotherapeutic drugs by the antivascular agent 5, 6-dimethylxanthenone-4-acetic acid (DMXAA). Cancer Chemother Pharmacol 2003;51:43-52 (Pubitemid 36057022)
11. Wilson WR, Li AE, Cowan DS, Siim BG. Enhancement of tumor radiation response by the antivascular agent 5,6-dimethylxanthenone-4-acetic acid. Int J Radiat Oncol Biol Phys 1998;42:905-8 (Pubitemid 28559440)
12. Murata R, Siemann DW, Overgaard J, Horsman MR. Improved tumor response by combining radiation and the vascular-damaging drug 5, 6-dimethylxanthenone-4- acetic acid. Radiat Res 2001;156:503-9 (Pubitemid 33027519)
13. Webster LK, Ellis AG, Kestell P, Rewcastle GW. Metabolism and elimination of 5,6-dimethylxanthenone- 4-acetic acid in the isolated perfused rat liver. Drug Metab Dispos 1995;23:363-8
14. Miners JO, Valente L, Lillywhite KJ, et al. Preclinical prediction of factors influencing the elimination of 5, 6-dimethylxanthenone-4-acetic acid, a new anticancer drug. Cancer Res 1997;57:284-9 (Pubitemid 27036607)
15. Zhou S, Kestell P, Baguley BC, Paxton JW. Preclinical factors influencing the relative contributions of Phase I and II enzymes to the metabolism of the experimental anti-cancer drug 5, 6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol 2003;65:109-20 (Pubitemid 35447845)
16. Zhou SF, Tingle MD, Kestell P, Paxton JW. Species differences in the metabolism of the antitumour agent 5, 6-dimethylxanthenone-4-acetic acid in vitro: implications for prediction of metabolic interactions in vivo. Xenobiotica 2002;32:87-107 (Pubitemid 34155217)
17. Zhou S, Chin R, Kestell P, et al. Effects of anticancer drugs on the metabolism of the anticancer drug 5, 6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes. Br J Clin Pharmacol 2001;52:129-36 (Pubitemid 32863069)
18. Zhao L, Kestell P, Philpott M, et al. Effects of the serotonin receptor antagonist cyproheptadine on the activity and pharmacokinetics of 5, 6-dimethylxanthenone-4-acetic acid (DMXAA). Cancer Chemother Pharmacol 2001;47:491-7 (Pubitemid 32477295)
19. Kestell P, Zhao L, Baguley BC, et al. Modulation of the pharmacokinetics of the antitumour agent 5, 6-dimethylxanthenone-4-acetic acid (DMXAA) in mice by thalidomide. Cancer Chemother Pharmacol 2000;46:135-41 (Pubitemid 30627476)
20. Zhou S, Paxton JW, Kestell P, Tingle MD. Reversible binding of the novel anti-tumour agent 5, 6-dimethylxanthenone-4-acetic acid to plasma proteins and its distribution into blood cells in various species. J Pharm Pharmacol 2001;53:463-71 (Pubitemid 32396536)
21. Baguley B, Jameson M, Zhao L, et al. Implications of the albumin binding properties of the anticancer drug 5, 6-dimethylxanthenone-4-acetic acid (DMXAA) to its clinical trial. Proc Aust Soc Clin Exp Pharmacol Toxicol 1998;5:208
22. Zhou S, Paxton JW, Tingle MD, Kestell P. Determination of the covalent adducts of the novel anti-cancer agent 5,6-dimethylxanthenone-4-acetic acid in biological samples by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 2001;757:343-8 (Pubitemid 32441755)
23. McKeage MJ, Kestell P, Denny WA, Baguley BC. Plasma pharmacokinetics of the antitumour agents 5, 6-dimethylxanthenone-4-acetic acid, xanthenone-4-acetic acid and flavone-8-acetic acid in mice. Cancer Chemother Pharmacol 1991;28:409-13
24. Kestell P, Paxton JW, Rewcastle GW, et al. Plasma disposition, metabolism and excretion of the experimental antitumour agent 5,6-dimethylxanthenone-4- acetic acid in the mouse, rat and rabbit. Cancer Chemother Pharmacol 1999;43:323-30 (Pubitemid 29075890)
25. Cao Z, Joseph WR, Browne WL, et al. Thalidomide increases both intra-tumoural tumour necrosis factor-alpha production and anti-tumour activity in response to 5, 6-dimethylxanthenone-4-acetic acid. Br J Cancer 1999;80:716-23 (Pubitemid 29209834)
26. Jameson MB, Thompson PI, Baguley BC, et al. Clinical aspects of a phase I trial of 5,6-dimethylxanthenone- 4-acetic acid (DMXAA), a novel antivascular agent. Br J Cancer 2003;88:1844-50 (Pubitemid 36829657)
27. Rustin GJ, Bradley C, Galbraith S, et al. 5,6-dimethylxanthenone-4-acetic acid (DMXAA), a novel antivascular agent: phase I clinical and pharmacokinetic study. Br J Cancer 2003;88:1160-7 (Pubitemid 36606327)
28. Galbraith SM, Rustin GJ, Lodge MA, et al. Effects of 5,6- dimethylxanthenone- 4-acetic acid on human tumor microcirculation assessed by dynamic contrast-enhanced magnetic resonance imaging. J Clin Oncol 2002;20:3826-40
29. McKeage MJ, Fong P, Jeffery M, et al. 5,6-Dimethylxanthenone-4-acetic acid in the treatment of refractory tumors: a phase I safety study of a vascular disrupting agent. Clin Cancer Res 2006;12:1776-84
30. Jameson MB, Sharp DM, Sissingh JI, et al. Transient retinal effects of 5, 6-dimethylxanthenone-4-acetic acid (DMXAA, ASA404), an antitumor vascular-disrupting agent in phase I clinical trials. Invest Ophthalmol Vis Sci 2009;50:2553-9
31. Head M, Jameson MB. The development of the tumor vascular-disrupting agent ASA404 (vadimezan, DMXAA): current status and future opportunities. Expert Opin Investig Drugs 2010;19:295-304
32. McKeage MJ, Von Pawel J, Reck M, et al. Randomised phase II study of ASA404 combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer. Br J Cancer 2008;99:2006-12
33. McKeage MJ, Reck M, Jameson MB, et al. Phase II study of ASA404 (vadimezan, 5,6-dimethylxanthenone-4- acetic acid/DMXAA) 1800 mg/m(2) combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer. Lung Cancer 2009;65:192-7
34. McKeage MJ, Jameson MB; AS1404-201 Study Group Investigators. Comparative outcomes of squamous and non-squamous non-small cell lung cancer (NSCLC) patients in phase II studies of ASA404 (DMXAA) - retrospective analysis of pooled data. J Thorac Dis 2010;2:199-204
35. Hida T, Tamiya M, Nishio M, et al. Phase I study of intravenous ASA404 (vadimezan) administered in combination with paclitaxel and carboplatin in Japanese patients with non-small cell lung cancer. Cancer Sci 2011;102:845-51
36. CASA404A1102. A safety, tolerability study of intravenous ASA404 administered in combination with docetaxel in Japanese patients with advanced or recurrent solid tumors. Novartis Clinical Trial Results Database 2010. Available from: www.novctrd.com/ ctrdWebApp/clinicaltrialrepository/ public/product.jsp? divisionId=2&productID=377& diseaseAreaID=1 [Last accessed 3 April 2011]
37. Gabra H; AS1404-202 Study Group Investigators. Phase II study of DMXAA combined with carboplatin and paclitaxel in recurrent ovarian cancer. J Clin Oncol 2006;24(20 Suppl):abstract 5032
38. Gabra H, Jameson M. AS1404-202 Study Group Investigators. Update on randomised phase II study of DMXAA (ASA404) combined with carboplatin and paclitaxel in recurrent ovarian cancer. ECCO 14. 2007. Barcelona, Spain. 20-9-2007
39. Pili R, Rosenthal MA, Mainwaring PN, et al. Phase II study on the addition of ASA404 (vadimezan; 5, 6-dimethylxanthenone-4-acetic acid) to docetaxel in CRMPC. Clin Cancer Res 2010;16:2906-14
40. Lara PN Jr, Douillard JY, Nakagawa K, et al. Randomized Phase III placebo-controlled trial of carboplatin and paclitaxel with or without the vascular disrupting agent vadimezan (ASA404) in advanced non-small-cell lung cancer. J Clin Oncol 2011;published online on June 27, 2011; DOI:10.1200/JCO.2011.35.0660:
41. Sandler A, Gray R, Perry MC, et al. Paclitaxel-carboplatin alone or with bevacizumab for non-small-cell lung cancer. N Engl J Med 2006;355:2542-50 (Pubitemid 44917502)
42. Available from: www.antisoma.com/asm/ media/press/pr2010/2010-11-11/. Antisoma.com 2010
43. Jameson MB, Baguley BC, Kestell P, et al. Pharmacokinetics of 5, 6-dimethylxanthenone-4-acetic acid (AS1404), a novel vascular disrupting agent, in phase I clinical trial. Cancer Chemother Pharmacol 2007;59:681-7 (Pubitemid 46295132)
44. Rosing H, Lustig V, van Warmerdam LJ, et al. Pharmacokinetics and metabolism of docetaxel administered as a 1-h intravenous infusion. Cancer Chemother Pharmacol 2000;45:213-18 (Pubitemid 30099768)
45. Zhao L, Ching LM, Kestell P, Baguley BC. Improvement of the antitumor activity of intraperitoneally and orally administered 5, 6-dimethylxanthenone-4- acetic acid by optimal scheduling. Clin Cancer Res 2003;9:6545-50 (Pubitemid 38031843)
46. Zhou S, Kestell P, Tingle MD, et al. A difference between the rat and mouse in the pharmacokinetic interaction of 5,6-dimethylxanthenone-4-acetic acid with thalidomide. Cancer Chemother Pharmacol 2001;47:541-4 (Pubitemid 32479222)
47. Chung F, Palmer BD, Muller GW, et al. Effect of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA). Oncol Res 2003;14:75-82 (Pubitemid 38166336)
48. Chung F, Liu J, Ching LM, Baguley BC. Consequences of increased vascular permeability induced by treatment of mice with 5,6-dimethylxanthenone-4- acetic acid (DMXAA) and thalidomide. Cancer Chemother Pharmacol 2008;61:497-502 (Pubitemid 350275985)
49. Ching LM, Browne WL, Tchernegovski R, et al. Interaction of thalidomide, phthalimide analogues of thalidomide and pentoxifylline with the antitumour agent 5, 6-dimethylxanthenone-4-acetic acid: concomitant reduction of serum tumour necrosis factor-alpha and enhancement of antitumour activity. Br J Cancer 1998;78:336-43 (Pubitemid 28336419)
50. Wang LC, Ching LM, Paxton JW, et al. Enhancement of the action of the antivascular drug 5, 6-dimethylxanthenone-4-acetic acid (DMXAA; ASA404) by non-steroidal anti-inflammatory drugs. Invest New Drugs 2009;27:280-4
51. Baguley BC, Zhan X, Finlay GJ. The antitumor action of ASA404 (vadimezan; DMXAA); potential involvement of vascular endothelial growth factor (VEGF). Proc Annu Meet Am Assoc Cancer Res 2010;101:#1660
52. Djeha H, Green C, Ireson C, Kelland LR. Synergistic in vivo antitumor activity in lung and colon cancer xenografts with the vascular disrupting agent DMXAA combined with bevacizumab. Proc Annu Meet Am Assoc Cancer Res 2006;2006:#233
53. Ching LM, Joseph WR, Baguley BC. Stimulation of macrophage tumouricidal activity by 5,6-dimethyl-xanthenone-4- acetic acid, a potent analogue of the antitumour agent flavone-8-acetic acid. Biochem Pharmacol 1992;44:192-5
54. Zhou S, Feng X, Kestell P, et al. Transport of the investigational anti-cancer drug 5,6- dimethylxanthenone-4-acetic acid and its acyl glucuronide by human intestinal Caco-2 cells. Eur J Pharm Sci 2005;24:513-24 (Pubitemid 40387265)
55. Bellnier DA, Gollnick SO, Camacho SH, et al. Treatment with the tumor necrosis factor-alpha-inducing drug 5, 6-dimethylxanthenone-4-acetic acid enhances the antitumor activity of the photodynamic therapy of RIF-1 mouse tumors. Cancer Res 2003;63:7584-90 (Pubitemid 37466677)
56. Marrero A, Becker T, Sunar U, et al. Aminolevulinic acid-photodynamic therapy combined with topically applied vascular disrupting agent vadimezan leads to enhanced antitumor responses. Photochem Photobiol 2011; Epub ahead of print
57. Seshadri M, Bellnier DA. The vascular disrupting agent 5, 6-dimethylxanthenone-4-acetic acid improves the antitumor efficacy and shortens treatment time associated with Photochlor-sensitized photodynamic therapy in vivo. Photochem Photobiol 2009;85:50-6
58. Shirey KA, Nhu QM, Yim KC, et al. The anti-tumor agent, 5, 6-dimethylxanthenone-4-acetic acid (DMXAA), induces IFN-{beta}-mediated antiviral activity in vitro and in vivo. J Leukoc Biol 2011;89:351-7