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

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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: 507.27
Molecular Weight: 507.680
Elemental Analysis: C, 63.88; H, 8.14; N, 2.76; O, 18.91; S, 6.3

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 450 Ready to ship
50mg USD 750 Ready to ship
100mg USD 1250 Ready to ship
200mg USD 1950 Ready to Ship
500mg USD 3250 Ready to Ship
1g USD 4650 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 Key: QXRSDHAAWVKZLJ-PVYNADRNSA-N

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

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

Biological target: Epothilone B is a microtubule stabilizer with a Ki of 0.71μM.
In vitro activity: Treatment with 0.2 nM patupilone alone only minimally decreased the MMP activity level (0.95 fold, p > 0.05) in comparison to the basal MMP activity level in CM derived from untreated control cells. Interestingly, pretreatment of cells with 0.2 nM patupilone completely abolished the IR-induced increase of MMP activity after 2 Gy and counteracted the irradiation-induced increase of MMP activity by 40% after 10 Gy of IR (p < 0.0001) (Figure 1A). A direct inhibitory effect of patupilone on MMPs could be excluded by addition of the MSA to CM, which did not affect MMP-activity (data not shown). Reference: Radiat Oncol. 2013; 8: 105. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3661365/
In vivo activity: A single dose of patupilone was strongly efficacious against the mammary BN472 tumor transplanted orthotopically in rats. One week after treatment, there was little or no tumor growth (T/C, 10.4%), mild diarrhea in some rats, and full survival (8 of 8), but there was significant body weight loss (−22 ± 2%). The overall exposure in these rats (mg/m2) was similar to the high dose given to B16/BL6 mice (i.e., 9 and 14 mg/m2 for rats and mice, respectively). Reference: Radiat Oncol. 2013 Apr 30;8:105. https://clincancerres.aacrjournals.org/content/11/21/7773.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 59.10

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
Formulation protocol: 1. Furmanova-Hollenstein P, Broggini-Tenzer A, Eggel M, Millard AL, Pruschy M. The microtubule stabilizer patupilone counteracts ionizing radiation-induced matrix metalloproteinase activity and tumor cell invasion. Radiat Oncol. 2013 Apr 30;8:105. doi: 10.1186/1748-717X-8-105. PMID: 23631818; PMCID: PMC3661365. 2. Carrara L, Guzzo F, Roque DM, Bellone S, Emiliano C, Sartori E, Pecorelli S, Schwartz PE, Rutherford TJ, Santin AD. Differential in vitro sensitivity to patupilone versus paclitaxel in uterine and ovarian carcinosarcoma cell lines is linked to tubulin-beta-III expression. Gynecol Oncol. 2012 Apr;125(1):231-6. doi: 10.1016/j.ygyno.2011.12.446. Epub 2011 Dec 29. PMID: 22209775; PMCID: PMC3303974. 3. Ferretti S, Allegrini PR, O'Reilly T, Schnell C, Stumm M, Wartmann M, Wood J, McSheehy PM. Patupilone induced vascular disruption in orthotopic rodent tumor models detected by magnetic resonance imaging and interstitial fluid pressure. Clin Cancer Res. 2005 Nov 1;11(21):7773-84. doi: 10.1158/1078-0432.CCR-05-1165. PMID: 16278399. 4. Hofstetter B, Vuong V, Broggini-Tenzer A, Bodis S, Ciernik IF, Fabbro D, Wartmann M, Folkers G, Pruschy M. Patupilone acts as radiosensitizing agent in multidrug-resistant cancer cells in vitro and in vivo. Clin Cancer Res. 2005 Feb 15;11(4):1588-96. doi: 10.1158/1078-0432.CCR-04-1800. PMID: 15746064.
In vitro protocol: 1. Furmanova-Hollenstein P, Broggini-Tenzer A, Eggel M, Millard AL, Pruschy M. The microtubule stabilizer patupilone counteracts ionizing radiation-induced matrix metalloproteinase activity and tumor cell invasion. Radiat Oncol. 2013 Apr 30;8:105. doi: 10.1186/1748-717X-8-105. PMID: 23631818; PMCID: PMC3661365. 2. Carrara L, Guzzo F, Roque DM, Bellone S, Emiliano C, Sartori E, Pecorelli S, Schwartz PE, Rutherford TJ, Santin AD. Differential in vitro sensitivity to patupilone versus paclitaxel in uterine and ovarian carcinosarcoma cell lines is linked to tubulin-beta-III expression. Gynecol Oncol. 2012 Apr;125(1):231-6. doi: 10.1016/j.ygyno.2011.12.446. Epub 2011 Dec 29. PMID: 22209775; PMCID: PMC3303974.
In vivo protocol: 1. Ferretti S, Allegrini PR, O'Reilly T, Schnell C, Stumm M, Wartmann M, Wood J, McSheehy PM. Patupilone induced vascular disruption in orthotopic rodent tumor models detected by magnetic resonance imaging and interstitial fluid pressure. Clin Cancer Res. 2005 Nov 1;11(21):7773-84. doi: 10.1158/1078-0432.CCR-05-1165. PMID: 16278399. 2. Hofstetter B, Vuong V, Broggini-Tenzer A, Bodis S, Ciernik IF, Fabbro D, Wartmann M, Folkers G, Pruschy M. Patupilone acts as radiosensitizing agent in multidrug-resistant cancer cells in vitro and in vivo. Clin Cancer Res. 2005 Feb 15;11(4):1588-96. doi: 10.1158/1078-0432.CCR-04-1800. PMID: 15746064.

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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.