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Epothilone B
  • Approved Drug Name
    Epothilone B
  • CAS NO.
    152044-54-7
  • Quality Standard
    Enterprise Standard
  • Packaging
    10G/Bag, 20G/Bag
  • Storage Condition
    Shading,Sealing,Cryopreservation(Below-20℃)
  • Certification
    Ongoing registration

Epothilone B(casno.152044-54-7) is a compound isolated from the myxobacterium Sorangium cellulosum. Similar to paclitaxel, patupilone 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. Patupilone may cause complete cell-cycle arrest.
Epothilone B(casno.152044-54-7) Indication: Investigated for use/treatment in ovarian cancer, lung cancer, brain cancer, breast cancer, and gastric cancer.
Categories of Epothilone B(casno.152044-54-7):
Antimitotic Agents
Antineoplastic Agents
Chemical Actions and Uses
Mitosis Modulators
Molecular Mechanisms of Pharmacological Action
Pharmacologic Actions
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Therapeutic Uses
Tubulin Modulators
Computed Descriptors of Epothilone B(casno.152044-54-7):
IUPAC Name of Epothilone B(casno.152044-54-7): 
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
InChI Key of Epothilone B(casno.152044-54-7):
QXRSDHAAWVKZLJ-PVYNADRNSA-N
InChI of Epothilone B(casno.152044-54-7):
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
Canonical SMILES of Epothilone B(casno.152044-54-7): 
CC1CCCC2(C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C
Isomeric SMILES of Epothilone B(casno.152044-54-7):
C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C)C
Epothilone B(casno.152044-54-7) Mechanism of action:
The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Epothilone B(casno.152044-54-7) possess the same biological effects as taxol both in vitro and in cultured cells. This is because they share the same binding site, as well as binding affinity to the microtubule. Like taxol, Epothilone B(casno.152044-54-7) binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. Furthermore, Epothilone B(casno.152044-54-7) has also been shown to induce tubulin polymerization into microtubules without the presence of GTP. This is caused by formation of microtubule bundles throughout the cytoplasm. Finally, Epothilone B(casno.152044-54-7) also causes cell cycle arrest at the G2-M transition phase, thus leading to cytotoxicity and eventually cell apoptosis.
Epothilone B(casno.152044-54-7) shows better activity than Epothilone A. The EC0.01 of Epothilone B(casno.152044-54-7) is 1.8 μM. Epothilone B(casno.152044-54-7) potently inhibits cell proliferation in HCT116 cells, with IC50 of 0.8 nM. Epothilone B(casno.152044-54-7) induces mitotic arrest and displays cytotoxicity in KB3-1, KBV-1, Hela, and Hs578T cells, with IC50 of 3 nM to 92 nM. Epothilone B(casno.152044-54-7) competes with Taxol in binding to microtubules, with IC50 of 3.3 μM. In MCF-7 cells overexpressing GFP-α-tubulin, Epothilone B(casno.152044-54-7) (3.5 nM) efficiently blocks microtubule dynamics. Meanwhile, Epothilone B(casno.152044-54-7) induces mitotic arrest with IC50 of 3.5 nM. In multiple myeloma (MM) cells, including RPMI 8226, U266, MM.1S, LR5, and MR20, Epothilone B(casno.152044-54-7) directly suppresses proliferation with IC50 of 1 nM to 10 nM. Similarly, Epothilone B(casno.152044-54-7) (10 nM) also induces cell cycle arrest and apoptosis. A recent study reveals that, in ovarian cancer Hey cells, Epothilone B(casno.152044-54-7) (5 nM–100 nM) enhances surface epithelial cell adhesion antigen (EpCAM), without affecting the transcription or the total cellular level of EpCAM.
In a mouse xenograft model of RPMI 8226 cells, Epothilone B(casno.152044-54-7) (2.5 mg/kg–4 mg/kg) prolongs survival and suppresses tumor growth. Similarly, in mouse xenograft models of prostate cancer cells, including DU145 and PC3, Epothilone B(casno.152044-54-7) at the same dose also inhibits tumor growth.