Patupilone (Epothilone B)

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MedKoo CAT#: 202160

CAS#: 152044-54-7

Description: Patupilone, also known as Epothilone B and EPO-906, 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.

Chemical Structure

Patupilone (Epothilone B)
CAS# 152044-54-7

Theoretical Analysis

MedKoo Cat#: 202160
Name: Patupilone (Epothilone B)
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, 6.3

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Same day
25.0mg USD 190.0 Same day
50.0mg USD 350.0 Same day
100.0mg USD 650.0 Same day
200.0mg USD 1050.0 Same day
500.0mg USD 2350.0 Same day
1.0g USD 4150.0 2 Weeks
2.0g USD 7450.0 2 Weeks
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Synonym: EPO906; EPO-906; EPO 906; EPO 906A; EPO B; (-)-Epothilone B; patupilone.

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


InChi Code: InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

SMILES Code: C/C([C@@H](OC(C[C@H](O)C1(C)C)=O)C[C@H](O2)[C@@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C1=O)=C\C3=CSC(C)=N3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 507.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Rogalska A, Bukowska B, Marczak A. Caspases and ROS - dependent mechanism of action mediated by combination of WP 631 and epothilone B. Anticancer Agents Med Chem. 2014;14(9):1261-70. PubMed PMID: 24913659.

2: Rogalska A, Gajek A, Marczak A. Epothilone B induces extrinsic pathway of apoptosis in human SKOV-3 ovarian cancer cells. Toxicol In Vitro. 2014 Jun;28(4):675-83. doi: 10.1016/j.tiv.2014.02.007. Epub 2014 Feb 26. PubMed PMID: 24583341.

3: Ceresa C, Avan A, Giovannetti E, Geldof AA, Avan A, Cavaletti G, Peters GJ. Characterization of and protection from neurotoxicity induced by oxaliplatin, bortezomib and epothilone-B. Anticancer Res. 2014 Jan;34(1):517-23. PubMed PMID: 24403510.

4: von Roemeling CA, Marlow LA, Kennedy WP, Kennedy GT, Copland JA, Menefee ME. Preclinical evaluation of the mTOR inhibitor, temsirolimus, in combination with the epothilone B analog, ixabepilone in renal cell carcinoma. Am J Cancer Res. 2013 Aug 14;3(4):390-401. eCollection 2013. PubMed PMID: 23977448; PubMed Central PMCID: PMC3744018.

5: Rogalska A, Gajek A, Marczak A. Analysis of epothilone B-induced cell death in normal ovarian cells. Cell Biol Int. 2013 Dec;37(12):1330-9. doi: 10.1002/cbin.10165. Epub 2013 Sep 12. PubMed PMID: 23955989.

6: Rogalska A, Szula E, Gajek A, Marczak A, Jóźwiak Z. Activation of apoptotic pathway in normal, cancer ovarian cells by epothilone B. Environ Toxicol Pharmacol. 2013 Sep;36(2):600-10. doi: 10.1016/j.etap.2013.06.003. Epub 2013 Jun 19. PubMed PMID: 23838010.

7: Churpek JE, Pro B, van Besien K, Kline J, Conner K, Wade JL 3rd, Hagemeister F, Karrison T, Smith SM. A phase 2 study of epothilone B analog BMS-247550 (NSC 710428) in patients with relapsed aggressive non-Hodgkin lymphomas. Cancer. 2013 May 1;119(9):1683-9. doi: 10.1002/cncr.27917. Epub 2013 Jan 10. PubMed PMID: 23310949.

8: Wang J, Sun BF, Cui K, Lin GQ. An efficient total synthesis of (-)-epothilone B. Org Lett. 2012 Dec 21;14(24):6354-7. doi: 10.1021/ol303148g. Epub 2012 Dec 7. PubMed PMID: 23214997.

9: Meier V, Geigy C, Grosse N, McSheehy P, Rohrer Bley C. Use of epothilone B (patupilone) in refractory lymphoma and advanced solid tumors in dogs. J Vet Intern Med. 2013 Jan-Feb;27(1):120-5. doi: 10.1111/jvim.12019. Epub 2012 Dec 3. PubMed PMID: 23205945.

10: Lu HM, Ye M. LC-MS/MS method for determination of epothilone B in rat plasma and its application in pharmacokinetic study. Arzneimittelforschung. 2012 Dec;62(12):609-13. doi: 10.1055/s-0032-1327695. Epub 2012 Oct 23. PubMed PMID: 23093482.

11: Baumgart T, Kriesen S, Hildebrandt G, Manda K. Effect of epothilone B on cell cycle, metabolic activity, and apoptosis induction on human epithelial cancer cells-under special attention of combined treatment with ionizing radiation. Cancer Invest. 2012 Oct;30(8):593-603. Epub 2012 Aug 21. PubMed PMID: 22909073.

12: Oehler C, Frei K, Rushing EJ, McSheehy PM, Weber D, Allegrini PR, Weniger D, Lütolf UM, Knuth A, Yonekawa Y, Barath K, Broggini-Tenzer A, Pruschy M, Hofer S. Patupilone (epothilone B) for recurrent glioblastoma: clinical outcome and translational analysis of a single-institution phase I/II trial. Oncology. 2012;83(1):1-9. doi: 10.1159/000339152. Epub 2012 Jun 8. PubMed PMID: 22688083.

13: Pagano A, Honoré S, Mohan R, Berges R, Akhmanova A, Braguer D. Epothilone B inhibits migration of glioblastoma cells by inducing microtubule catastrophes and affecting EB1 accumulation at microtubule plus ends. Biochem Pharmacol. 2012 Aug 15;84(4):432-43. doi: 10.1016/j.bcp.2012.05.010. Epub 2012 May 23. PubMed PMID: 22634050.

14: Baumgart T, Klautke G, Kriesen S, Kuznetsov SA, Weiss DG, Fietkau R, Hildebrandt G, Manda K. Radiosensitizing effect of epothilone B on human epithelial cancer cells. Strahlenther Onkol. 2012 Feb;188(2):177-84. doi: 10.1007/s00066-011-0029-4. Epub 2012 Jan 12. PubMed PMID: 22234539.

15: Oehler C, von Bueren AO, Furmanova P, Broggini-Tenzer A, Orlowski K, Rutkowski S, Frei K, Grotzer MA, Pruschy M. The microtubule stabilizer patupilone (epothilone B) is a potent radiosensitizer in medulloblastoma cells. Neuro Oncol. 2011 Sep;13(9):1000-10. doi: 10.1093/neuonc/nor069. Epub 2011 Jul 9. PubMed PMID: 21743064; PubMed Central PMCID: PMC3158010.

16: Gan PP, McCarroll JA, Byrne FL, Garner J, Kavallaris M. Specific β-tubulin isotypes can functionally enhance or diminish epothilone B sensitivity in non-small cell lung cancer cells. PLoS One. 2011;6(6):e21717. doi: 10.1371/journal.pone.0021717. Epub 2011 Jun 29. PubMed PMID: 21738778; PubMed Central PMCID: PMC3126859.

17: Pellicciotta I, Yang CP, Goldberg GL, Shahabi S. Epothilone B enhances Class I HLA and HLA-A2 surface molecule expression in ovarian cancer cells. Gynecol Oncol. 2011 Sep;122(3):625-31. doi: 10.1016/j.ygyno.2011.05.007. Epub 2011 May 28. PubMed PMID: 21621254.

18: Vollmer LL, Jiménez M, Camarco DP, Zhu W, Daghestani HN, Balachandran R, Reese CE, Lazo JS, Hukriede NA, Curran DP, Day BW, Vogt A. A simplified synthesis of novel dictyostatin analogues with in vitro activity against epothilone B-resistant cells and antiangiogenic activity in zebrafish embryos. Mol Cancer Ther. 2011 Jun;10(6):994-1006. doi: 10.1158/1535-7163.MCT-10-1048. Epub 2011 Apr 13. PubMed PMID: 21490306; PubMed Central PMCID: PMC3112307.

19: Schiess R, Gertsch J, Schweizer WB, Altmann KH. Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants. Org Lett. 2011 Mar 18;13(6):1436-9. doi: 10.1021/ol200114k. Epub 2011 Feb 21. PubMed PMID: 21338105.

20: Khrapunovich-Baine M, Menon V, Yang CP, Northcote PT, Miller JH, Angeletti RH, Fiser A, Horwitz SB, Xiao H. Hallmarks of molecular action of microtubule stabilizing agents: effects of epothilone B, ixabepilone, peloruside A, and laulimalide on microtubule conformation. J Biol Chem. 2011 Apr 1;286(13):11765-78. doi: 10.1074/jbc.M110.162214. Epub 2011 Jan 18. PubMed PMID: 21245138; PubMed Central PMCID: PMC3064228.

Additional Information

Chemical structure comparison between Ixabepilone (azaepothilone B or BMS-247550) and Patupilone (Epothilone B)