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MedKoo Cat#: 202160 | Name: Patupilone (Epothilone B)
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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)
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: 507.2655

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
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 1,950.00 Ready to Ship
500mg USD 3,250.00 Ready to Ship
1g USD 4,650.00 2 Weeks
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Related CAS #
No Data
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
Solvent mg/mL mM
Solubility
DMSO 30.0 59.10
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Khan S, Huang Y, Timuçin D, Bailey S, Lee S, Lopes J, Gaunce E, Mosberger J, Zhan M, Abdelrahman B, Zeng X, Wiest MC. Microtubule-stabilizer epothilone B delays anesthetic-induced unconsciousness in rats. eNeuro. 2024 Aug 15:ENEURO.0291-24.2024. doi: 10.1523/ENEURO.0291-24.2024. Epub ahead of print. PMID: 39147581. 2: Liu R, Chu W, Liu X, Hong J, Wang H. Establishment of Golgi apparatus-related genes signature to predict the prognosis and immunotherapy response in gastric cancer patients. Medicine (Baltimore). 2024 Mar 15;103(11):e37439. doi: 10.1097/MD.0000000000037439. PMID: 38489711; PMCID: PMC10939665. 3: Ma C, Zhao H, Sun Y, Ding W, Wang H, Li Y, Gu Z. Deciphering disulfidptosis: Uncovering a lncRNA-based signature for prognostic assessment, personalized immunotherapy, and therapeutic agent selection in lung adenocarcinoma patients. Cell Signal. 2024 May;117:111105. doi: 10.1016/j.cellsig.2024.111105. Epub 2024 Feb 16. PMID: 38369264. 4: Chen DQ, Xie Y, Cao LQ, Fleishman JS, Chen Y, Wu T, Yang DH. The role of ABCC10/MRP7 in anti-cancer drug resistance and beyond. Drug Resist Updat. 2024 Mar;73:101062. doi: 10.1016/j.drup.2024.101062. Epub 2024 Jan 29. PMID: 38330827. 5: El-Sayed ASA, Shindia A, Ammar H, Seadawy MG, Khashana SA. Bioprocessing of Epothilone B from Aspergillus fumigatus under solid state fermentation: Antiproliferative activity, tubulin polymerization and cell cycle analysis. BMC Microbiol. 2024 Jan 30;24(1):43. doi: 10.1186/s12866-024-03184-w. PMID: 38291363; PMCID: PMC10829302. 6: Wang S, Wang P, Li SJ, Chen YH, Sun ZJ, Lei A. Electrochemical flow aziridination of unactivated alkenes. Natl Sci Rev. 2023 Jul 3;10(10):nwad187. doi: 10.1093/nsr/nwad187. PMID: 38059062; PMCID: PMC10697417. 7: Ma C, Gu Z, Ding W, Li F, Yang Y. Crosstalk between copper homeostasis and cuproptosis reveals a lncRNA signature to prognosis prediction, immunotherapy personalization, and agent selection for patients with lung adenocarcinoma. Aging (Albany NY). 2023 Nov 26;15(22):13504-13541. doi: 10.18632/aging.205281. Epub 2023 Nov 26. PMID: 38011277; PMCID: PMC10713389. 8: Yon DK, Kim YJ, Park DC, Jung SY, Kim SS, Yeo JH, Lee J, Lee JM, Yeo SG. Induction of Autophagy and Its Role in Peripheral Nerve Regeneration after Peripheral Nerve Injury. Int J Mol Sci. 2023 Nov 11;24(22):16219. doi: 10.3390/ijms242216219. PMID: 38003409; PMCID: PMC10671617. 9: Chen X, Yuan Q, Guan H, Shi X, Sun J, Wu Z, Ren J, Xia S, Shang D. Identification and characterization of interferon-γ signaling-based personalized heterogeneity and therapeutic strategies in patients with pancreatic cancer. Front Oncol. 2023 Oct 24;13:1227606. doi: 10.3389/fonc.2023.1227606. PMID: 37941546; PMCID: PMC10628740. 10: Omar Khudhur Z, Ziyad Abdulqadir S, Faqiyazdin Ahmed Mzury A, Aziz Rasoul A, Wasman Smail S, Ghayour MB, Abdolmaleki A. Epothilone B loaded in acellular nerve allograft enhanced sciatic nerve regeneration in rats. Fundam Clin Pharmacol. 2024 Apr;38(2):307-319. doi: 10.1111/fcp.12961. Epub 2023 Oct 19. PMID: 37857403. 11: Guo Y, Wang R, Shi J, Yang C, Ma P, Min J, Zhao T, Hua L, Song Y, Li J, Su H. Machine learning-based integration develops a metabolism-derived consensus model for improving immunotherapy in pancreatic cancer. J Immunother Cancer. 2023 Sep;11(9):e007466. doi: 10.1136/jitc-2023-007466. PMID: 37739440; PMCID: PMC10533800. 12: Li H, Sha X, Wang W, Huang Z, Zhang P, Liu L, Wang S, Zhou Y, He S, Shi J. Identification of lysosomal genes associated with prognosis in lung adenocarcinoma. Transl Lung Cancer Res. 2023 Jul 31;12(7):1477-1495. doi: 10.21037/tlcr-23-14. Epub 2023 Jul 18. PMID: 37577321; PMCID: PMC10413022. 13: Xu Y, Qian L, Fang M, Liu Y, Xu ZJ, Ge X, Zhang Z, Liu ZP, Lou H. Tumor selective self-assembled nanomicelles of carbohydrate-epothilone B conjugate for targeted chemotherapy. Eur J Med Chem. 2023 Nov 5;259:115693. doi: 10.1016/j.ejmech.2023.115693. Epub 2023 Jul 29. PMID: 37531745. 14: Yu S, Tang L, Zhang Q, Li W, Yao S, Cai Y, Cheng H. A cuproptosis-related lncRNA signature for predicting prognosis and immunotherapy response of lung adenocarcinoma. Hereditas. 2023 Jul 24;160(1):31. doi: 10.1186/s41065-023-00293-w. PMID: 37482612; PMCID: PMC10364405. 15: Nekkalapudi AR, Navuluri S, Pippalla S, Katari NK, Cholleti VK, Bapatu HR. Development of HPLC Method for Ixabepilone (Oncology Drug) in Bulk and Dosage Form: Quantification of Impurities and Forced Degradation Studies. J Chromatogr Sci. 2024 Mar 23;62(3):222-231. doi: 10.1093/chromsci/bmad049. PMID: 37465887. 16: Geng N, Yu Z, Zeng X, Xu D, Gao H, Yang M, Huang X. Nuclear Tubulin Enhances CXCR4 Transcription and Promotes Chemotaxis Through TCF12 Transcription Factor in human Hematopoietic Stem Cells. Stem Cell Rev Rep. 2023 Jul;19(5):1328-1339. doi: 10.1007/s12015-023-10543-z. Epub 2023 Apr 17. PMID: 37067645. 17: Neishaboori AM, Tavallaei MJ, Toloui A, Ahmadzadeh K, Alavi SNR, Lauran M, Hosseini M, Yousefifard M. Effects of Epothilone Administration on Locomotion Recovery after Spinal Cord Injury: A Systematic Review of Animal Studies. Asian Spine J. 2023 Aug;17(4):761-769. doi: 10.31616/asj.2022.0005. Epub 2023 Apr 17. PMID: 37062538; PMCID: PMC10460658. 18: Chen PJ, Lin ES, Su HH, Huang CY. Cytotoxic, Antibacterial, and Antioxidant Activities of the Leaf Extract of Sinningia bullata. Plants (Basel). 2023 Feb 14;12(4):859. doi: 10.3390/plants12040859. Erratum in: Plants (Basel). 2023 Oct 13;12(20):3557. doi: 10.3390/plants12203557. PMID: 36840206; PMCID: PMC9967939. 19: Ma Q, Hui Y, Huang BR, Yang BF, Li JX, Fan TT, Gao XC, Ma DY, Chen WF, Pei ZX. Ferroptosis and cuproptosis prognostic signature for prediction of prognosis, immunotherapy and drug sensitivity in hepatocellular carcinoma: development and validation based on TCGA and ICGC databases. Transl Cancer Res. 2023 Jan 30;12(1):46-64. doi: 10.21037/tcr-22-2203. Epub 2022 Dec 19. PMID: 36760376; PMCID: PMC9906058. 20: Griffin JM, Hingorani Jai Prakash S, Bockemühl T, Benner JM, Schaffran B, Moreno-Manzano V, Büschges A, Bradke F. Rehabilitation enhances epothilone- induced locomotor recovery after spinal cord injury. Brain Commun. 2023 Jan 13;5(1):fcad005. doi: 10.1093/braincomms/fcad005. Erratum in: Brain Commun. 2023 Feb 17;5(1):fcad029. doi: 10.1093/braincomms/fcad029. PMID: 36744011; PMCID: PMC9893225.

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