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MedKoo product information:

 

Patupilone

 

Desciprtion of Patupilone (Epothilone B): Epothilone B is a compound isolated from the myxobacterium Sorangium cellulosum. Similar to paclitaxel, epothilone B induces microtubule polymerization and stabilizes microtubules against depolymerization conditions. In addition to promoting tubulin polymerization and stabilization of microtubules, this agent is cytotoxic for cells overexpressing P-glycoprotein, a characteristic that distinguishes it from the taxanes. Epothilone B may cause complete cell-cycle arrest. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

 

Current developer:    Novartis Pharma AG.

   

MedKoo Code#:  202160

Name:  Patupilone

CAS#:  152044-54-7

   

Synonym:  (-)-Epothilone B; patupilone. Code name: EPO906. 

  

IUPAC/Chemical name: 

(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

  

Chemical structure Theoretical analysis

 

 

  

MedKoo Code#:  202160
Name:  Patupilone
CAS#:  152044-54-7

Chemical Formula: C27H41NO6S

Exact Mass: 507.26546

Molecular Weight: 507.68

Elemental Analysis: C, 63.88; H, 8.14; N, 2.76; O, 18.91; S, 6.32

  

   

Availability and price:

 

Patupilone (Epothilone B) is in stock, estimated delivery time 7-9 business days.

10 mg / $290.00 (minimum order)

25 mg / $550.00

50 mg / $950.00

100mg / $1,650.00

200mg / $2,950.00

Grams in stock at low price.

(YYPharma, TZCB)

 

To inquire quotation and lead time or to ask questions, please send email to sales@medkoo.com to describe your needs. A representative will respond your email shortly. We offer big discount for orders of bulk quantities.

 

 

Information about this agent

 

 

References

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4: Stalder MW, Anthony CT, Woltering EA. Metronomic Dosing Enhances The Anti-Angiogenic Effect of Epothilone B. J Surg Res. 2009 Dec 30. [Epub ahead of print] PubMed PMID: 20338584.

5: Yang CP, Liu L, Ikui AE, Horwitz SB. The interaction between mitotic checkpoint proteins, CENP-E and BubR1, is diminished in epothilone B-resistant A549 cells. Cell Cycle. 2010 Mar 4;9(6). [Epub ahead of print] PubMed PMID: 20237434.

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26: Forli S, Manetti F, Altmann KH, Botta M. Evaluation of novel epothilone analogues by means of a common pharmacophore and a QSAR pseudoreceptor model for taxanes and epothilones. ChemMedChem. 2010 Jan;5(1):35-40. PubMed PMID: 19904799.

27: Po'uha ST, Shum MS, Goebel A, Bernard O, Kavallaris M. LIM-kinase 2, a regulator of actin dynamics, is involved in mitotic spindle integrity and sensitivity to microtubule-destabilizing drugs. Oncogene. 2010 Jan 28;29(4):597-607. Epub 2009 Nov 2. PubMed PMID: 19881550.

28: Fogh S, Machtay M, Werner-Wasik M, Curran WJ Jr, Bonanni R, Axelrod R, Andrews D, Dicker AP. Phase I trial using patupilone (epothilone B) and concurrent radiotherapy for central nervous system malignancies. Int J Radiat Oncol Biol Phys. 2010 Jul 15;77(4):1009-16. Epub 2009 Oct 30. PubMed PMID: 19879067.

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38: Michaud LB. The epothilones: how pharmacology relates to clinical utility. Ann Pharmacother. 2009 Jul;43(7):1294-309. Epub 2009 Jul 7. Review. PubMed PMID: 19584389.

39: Wang J, Zhang H, Ying L, Wang C, Jiang N, Zhou Y, Wang H, Bai H. Five new epothilone metabolites from Sorangium cellulosum strain So0157-2. J Antibiot (Tokyo). 2009 Sep;62(9):483-7. Epub 2009 Jul 3. PubMed PMID: 19575038.

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46: Gupta D, Mani S. The efficacy and safety of ixabepilone monotherapy in the treatment of breast and gynecologic malignancies. Expert Opin Drug Saf. 2009 Jan;8(1):81-8. Review. PubMed PMID: 19236220.

47: Bley CR, Jochum W, Orlowski K, Furmanova P, Vuong V, McSheehy PM, Pruschy M. Role of the microenvironment for radiosensitization by patupilone. Clin Cancer Res. 2009 Feb 15;15(4):1335-42. PubMed PMID: 19228735.

48: Cigler T, Vahdat L. Integrating epothilones into the treatment of patients with metastatic breast cancer: clinical perspectives on incorporating recent data in the practice setting. Clin Breast Cancer. 2008 Dec;8 Suppl 4:S166-70. Review. PubMed PMID: 19158037.

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52: Dumontet C, Jordan MA, Lee FF. Ixabepilone: targeting betaIII-tubulin expression in taxane-resistant malignancies. Mol Cancer Ther. 2009 Jan;8(1):17-25. Review. PubMed PMID: 19139109.

53: Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD. Human multidrug resistance protein 7 (ABCC10) is a resistance factor for nucleoside analogues and epothilone B. Cancer Res. 2009 Jan 1;69(1):178-84. PubMed PMID: 19118001; PubMed Central PMCID: PMC2745904.

54: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Oct;30(8):643-72. PubMed PMID: 19088949.

55: Rivera E, Lee J, Davies A. Clinical development of ixabepilone and other epothilones in patients with advanced solid tumors. Oncologist. 2008 Dec;13(12):1207-23. Epub 2008 Dec 16. Review. PubMed PMID: 19088324.

56: Hussain A, DiPaola RS, Baron AD, Higano CS, Tchekmedyian NS, Johri AR. Phase II trial of weekly patupilone in patients with castration-resistant prostate cancer. Ann Oncol. 2009 Mar;20(3):492-7. Epub 2008 Dec 15. PubMed PMID: 19087985.

57: Mozzetti S, Iantomasi R, De Maria I, Prislei S, Mariani M, Camperchioli A, Bartollino S, Gallo D, Scambia G, Ferlini C. Molecular mechanisms of patupilone resistance. Cancer Res. 2008 Dec 15;68(24):10197-204. PubMed PMID: 19074887.

58: Gertsch J, Meier S, Müller M, Altmann KH. Differential effects of natural product microtubule stabilizers on microtubule assembly: single agent and combination studies with taxol, epothilone B, and discodermolide. Chembiochem. 2009 Jan 5;10(1):166-75. PubMed PMID: 19058273.

59: Lee JJ, Kelly WK. Epothilones: tubulin polymerization as a novel target for prostate cancer therapy. Nat Clin Pract Oncol. 2009 Feb;6(2):85-92. Epub 2008 Dec 2. Review. PubMed PMID: 19048010.

60: Keck GE, Giles RL, Cee VJ, Wager CA, Yu T, Kraft MB. Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions. J Org Chem. 2008 Dec 19;73(24):9675-91. PubMed PMID: 18991385; PubMed Central PMCID: PMC2736362.

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62: Goodin S. Ixabepilone: a novel microtubule-stabilizing agent for the treatment of metastatic breast cancer. Am J Health Syst Pharm. 2008 Nov 1;65(21):2017-26. Review. PubMed PMID: 18945860.

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66: Quick QA. Epothilone B induces glioblastoma cell death via survivin down-regulation. Exp Oncol. 2008 Sep;30(3):195-201. PubMed PMID: 18806741.

67: Park SR, Park JW, Jung WS, Han AR, Ban YH, Kim EJ, Sohng JK, Sim SJ, Yoon YJ. Heterologous production of epothilones B and D in Streptomyces venezuelae. Appl Microbiol Biotechnol. 2008 Nov;81(1):109-17. Epub 2008 Sep 4. PubMed PMID: 18769916.

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75: Buzdar AU. Clinical experience with epothilones in patients with breast cancer. Clin Breast Cancer. 2008 Mar;8 Suppl 2:S71-8. Review. PubMed PMID: 18637402.

76: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Apr;30(3):231-51. PubMed PMID: 18597009.

77: Hoffmann J, Vitale I, Buchmann B, Galluzzi L, Schwede W, Senovilla L, Skuballa W, Vivet S, Lichtner RB, Vicencio JM, Panaretakis T, Siemeister G, Lage H, Nanty L, Hammer S, Mittelstaedt K, Winsel S, Eschenbrenner J, Castedo M, Demarche C, Klar U, Kroemer G. Improved cellular pharmacokinetics and pharmacodynamics underlie the wide anticancer activity of sagopilone. Cancer Res. 2008 Jul 1;68(13):5301-8. PubMed PMID: 18593931.

78: Khawaja NR, Carré M, Kovacic H, Estève MA, Braguer D. Patupilone-induced apoptosis is mediated by mitochondrial reactive oxygen species through Bim relocalization to mitochondria. Mol Pharmacol. 2008 Oct;74(4):1072-83. Epub 2008 Jul 1. PubMed PMID: 18593821.

79: Swain SM, Arezzo JC. Neuropathy associated with microtubule inhibitors: diagnosis, incidence, and management. Clin Adv Hematol Oncol. 2008 Jun;6(6):455-67. Review. PubMed PMID: 18567992.

80: Moulder SL. Ixabepilone for the treatment of taxane-refractory breast cancer. Future Oncol. 2008 Jun;4(3):333-40. Review. PubMed PMID: 18518758.

81: Goodin S. Novel cytotoxic agents: epothilones. Am J Health Syst Pharm. 2008 May 15;65(10 Suppl 3):S10-5. Review. PubMed PMID: 18463327.

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83: Goel S, Cohen M, Cömezoglu SN, Perrin L, André F, Jayabalan D, Iacono L, Comprelli A, Ly VT, Zhang D, Xu C, Humphreys WG, McDaid H, Goldberg G, Horwitz SB, Mani S. The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of ixabepilone: a first in class epothilone B analogue in late-phase clinical development. Clin Cancer Res. 2008 May 1;14(9):2701-9. PubMed PMID: 18451235.

84: Vahdat LT. Clinical studies with epothilones for the treatment of metastatic breast cancer. Semin Oncol. 2008 Apr;35(2 Suppl 2):S22-30; quiz S40. Review. PubMed PMID: 18410796.

85: Burris HA 3rd. Preclinical investigations with epothilones in breast cancer models. Semin Oncol. 2008 Apr;35(2 Suppl 2):S15-21; quiz S39. Review. PubMed PMID: 18410795.

86: Altmann KH, Memmert K. Epothilones as lead structures for new anticancer drugs--pharmacology, fermentation, and structure-activity-relationships. Prog Drug Res. 2008;66:273, 275-334. Review. PubMed PMID: 18416309.

87: Vahdat L. Ixabepilone: a novel antineoplastic agent with low susceptibility to multiple tumor resistance mechanisms. Oncologist. 2008 Mar;13(3):214-21. Review. PubMed PMID: 18378531.

88: Pivot X, Villanueva C, Chaigneau L, Nguyen T, Demarchi M, Maurina T, Stein U, Borg C. Ixabepilone, a novel epothilone analog in the treatment of breast cancer. Expert Opin Investig Drugs. 2008 Apr;17(4):593-9. Review. PubMed PMID: 18363523.

89: Harrison M, Swanton C. Epothilones and new analogues of the microtubule modulators in taxane-resistant disease. Expert Opin Investig Drugs. 2008 Apr;17(4):523-46. Review. PubMed PMID: 18363517.

90: Lee FY, Smykla R, Johnston K, Menard K, McGlinchey K, Peterson RW, Wiebesiek A, Vite G, Fairchild CR, Kramer R. Preclinical efficacy spectrum and pharmacokinetics of ixabepilone. Cancer Chemother Pharmacol. 2009 Jan;63(2):201-12. Epub 2008 Mar 19. PubMed PMID: 18350296.

91: Lee FY, Borzilleri R, Fairchild CR, Kamath A, Smykla R, Kramer R, Vite G. Preclinical discovery of ixabepilone, a highly active antineoplastic agent. Cancer Chemother Pharmacol. 2008 Dec;63(1):157-66. Epub 2008 Mar 18. Review. PubMed PMID: 18347795.

92: Lee JJ, Swain SM. The epothilones: translating from the laboratory to the clinic. Clin Cancer Res. 2008 Mar 15;14(6):1618-24. Review. PubMed PMID: 18347162.

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