E2656
(−)-Epothilone B
from Sorangium cellulosum, ≥98% (HPLC)
Synonym(s):
EPO906, EpoB, Patupilone
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About This Item
Empirical Formula (Hill Notation):
C27H41NO6S
CAS Number:
Molecular Weight:
507.68
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
lyophilized powder
Quality level:
Storage condition:
desiccated, protect from light
biological source
Sorangium cellulosum
Quality Level
assay
≥98% (HPLC)
form
lyophilized powder
storage condition
desiccated, protect from light
color
white to off-white
storage temp.
−20°C
SMILES string
[H][C@]1(C[C@]2([H])O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)\C(C)=C\c3csc(C)n3
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
InChI key
QXRSDHAAWVKZLJ-PVYNADRNSA-N
General description
Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).
Biochem/physiol Actions
(-)-Epothilone B is a microtubule (MT) stabilizing drug and natural macrolide antitumor from myxobacteria Sorangium cellulosum. EpoB has similar biological properties to EpoA. However, EpoB is 10-fold more potent than EpoA against P-glycoprotein-expressing multidrug resistant (MDR) cells (IC50 = 2 nM for MDR CCRF-CEM/VBL100 cells). (-)-Epothilone B is similar to paclitaxel in binding displacement, and a substitution for paclitaxel in dependent cell growth. EpoB causes cell cycle arrest (IC50 = 3.5 nM).
EpoB is a microtubule stabilizing drug and natural macrolide antitumor.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Phase II clinical trial of ixabepilone (BMS-247550), an epothilone B analog, as first-line therapy in patients with metastatic breast cancer previously treated with anthracycline chemotherapy
Roche H, et al.
Journal of Clinical Oncology, 25(23), 3415-3420 (2007)
BMS-247550: a novel epothilone analog with a mode of action similar to paclitaxel but possessing superior antitumor efficacy
Lee FYF, et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 7(5), 1429-1437 (2001)
Christoph Grohmann et al.
Cell death & disease, 12(3), 268-268 (2021-03-14)
Targeting cell division by chemotherapy is a highly effective strategy to treat a wide range of cancers. However, there are limitations of many standard-of-care chemotherapies: undesirable drug toxicity, side-effects, resistance and high cost. New small molecules which kill a wide
Global Trade Item Number
| SKU | GTIN |
|---|---|
| E2656-1MG | 04061822415348 |
| E2656-5MG | 04061833065921 |