E-5500 Epothilone B, Free Base, >99%

Synonyms : [EPO-906] [EpoB]

Related Terms : [Patupilone]

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  • 1 mg
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  • 2 mg
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  • 38
  • 5,800
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  • 5 mg
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  • 10 mg
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  • 25 mg
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  • 50 mg
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  • 367
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  • 100 mg
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  • M.W. 507.68
  • C27H41NO6S
  • [152044-54-7]
  • M.I. 14: 3628

Storage: Store at or below -20 ºC. Solubility: Soluble in DMSO at 40 mg/mL; soluble in ethanol at 40 mg/mL; very poorly soluble in water; maximum solubility in plain water is estimated to be about 10-50 µM buffers, serum, or other additives may increase or decrease the aqueous solubility. Disposal: A.

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  • Epothilones A-F are anticancer drugs. They induce microtubule polymerization at submicromolar concentrations and lead to death of cancer cells. Goodin, S., et al. "Epothilones: mechanism of action and biologic activity." J. Clin. Oncol. 22: 2015-2025 (2004).
  • Epothilone B possess essentially all the biological effects of taxol both in vitro and in cultured cells. Epothilone B caused cell cycle arrest at the G2-M transition (EC50 = 32 nM for Hela cells and 3 nM for Hs578T), similar to taxol (EC50 = 7 nM for Hela cells and 10 nM for Hs578T). Epothilone B leads to cytotoxicity (EC50 = 40 nM for Hela cells and 6 nM for Hs578T), also similar to taxol (EC50 = 20 nM for Hela cells and 15 nM for Hs578T). However, epothilone B retains a much greater mitotic arrest at the G2-M transition and toxicity against P-glycoprotein-expressing multiple drug resistant KBV-1 cells (EC50 = 92 nM and 58 nM, respectively) than paclitaxel (EC50 = 17 µM and 23 µM, respectively). Bollag, D.M., et al. "Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action." Cancer Res. 55: 2325-2333 (1995).
  • Two acquired β-tubulin mutations [β274(Thr-->Ile) and β282(Arg-->Gln)] near the taxane binding site exhibit impaired epothilone- and taxane-driven tubulin polymerization. Giannakakou, P., et al. "A common pharmacophore for epothilone and taxanes: molecular basis for drug resistance conferred by tubulin mutations in human cancer cells." Proc. Natl. Acad. Sci. USA 97: 2904-2909 (2000).
  • Purified tubulin from parental 1A9 human ovarian carcinoma cells demonstrated paclitaxel-driven increased polymerization while the resistant cell tubulin with a mutation at 270 (Phe --> Val) or 364 (Ala --> Thr) barely polymerized under identical conditions. In contrast, the resistant cells retained sensitivity to epothilone B and the assembly was increased. Giannakakou, P., et al. "Paclitaxel-resistant human ovarian cancer cells have mutant beta-tubulins that exhibit impaired paclitaxel-driven polymerization." J. Biol. Chem. 272: 17118-17125 (1997).
  • Epothilone B inhibited the growth of paclitaxel-sensitive human carcinoma cell lines including A549 (lung), NCI-H460 (Lung), HCT-116 (colon), DU145 (prostate), PC-3M (prostate), MDA-MB-231 (breast), BT-20 (breast), ZR-75-1 (breast), T-24 (bladder), and A-431 (epidermoid) with IC50's ranging from 0.13 nM to 0.64 nM. It also inhibited the growth of paclitaxel-resistant human cancer cell lines including CCRF-CEM (leukemia), CCRF-CEM/VBL100, SW620 (colon), SW620AD-300, KB-31, KB-8511, 1A9 (ovarian), 1A9PTX22, MCF-7 (breast), MCF-7/ADR, and HCT-15 (colon) with IC50's of 0.06 nM to 2.9 nM. Altmann, K.H., et al. "Epothilones and related structures--a new class of microtubule inhibitors with potent in vivo antitumor activity." Biochim. Biophys. Acta 1470: M79-M91 (2000).
  • Diarrhea is the dose-limiting toxicity for epothilone B in clinical trials for patients with lung, ovarian and prostate cancers. Larkin, J.M.G., et al. "Patupilone" Drugs Fut. 32: 323 (2007).
  • Another CAS number previously assigned to epothilone B, 681125-91-7, has been deleted by CAS and is no longer in use.
  • Epothilone B is the active ingredient in the drug product sold under the trade name Ixempra®.  This drug is currently approved in at least one country as a microtubule inhibitor, in combination with capecitabine is indicated for the treatment of metastatic or locally advanced breast cancer in patients after failure of an anthracycline and a taxane.  Ixempra® monotherapy is indicated for the treatment of metastatic or locally advanced breast cancer in patients after failure of an anthracycline, a taxane, and capecitabine.  NOTE:  THE EPOTHILONE B SOLD BY LC LABORATORIES FOR RESEARCH IS NOT IXEMPRA®, AND IS NOT FOR HUMAN USE.
  • Sold for laboratory or manufacturing purposes only; not for human, veterinary, food, or household use.
  • This product is offered for R&D use in accordance with (i) 35 USC 271(e)+A13(1) in the U.S.; (ii) Section 69.1 of Japanese Patent Law in Japan; (iii) Section 11, No. 2 of the German Patent Act of 1981 in Germany; (iv) Section 60, Paragraph 5b of the U.K. Patents Act of 1977 in the U.K.; (v) Sections 55.2(1) and 55.2(6) and other common law exemptions of Canadian patent law; (vi) Section 68B of the Patents Act of 1953 in New Zealand together with the amendment of same by the Statutes Amendment Bill of 2002; (vii) such related legislation and/or case law as may be or become applicable in the aforementioned countries; and (viii) such similar laws and rules as may apply in various other countries.
  • Not available in some countries; not available to some institutions; not available for some uses.