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Epothilone B

Epothilone B Structure
CAS No.
152044-54-7
Chemical Name:
Epothilone B
Synonyms
CS-556;EPO 906A;atupilone;EPOTHILONE;Patupilone;Ebomycin B;Epothilon B;Epothilone B;Oncology API;Epothilone B, >=98%
CBNumber:
CB0972824
Molecular Formula:
C27H41NO6S
Molecular Weight:
507.68
MOL File:
152044-54-7.mol
MSDS File:
SDS
Modify Date:
2024/7/25 20:04:51

Epothilone B Properties

Melting point 95-97°C
alpha D21 -35° (c = 0.7 in methanol)
Boiling point 680.2±55.0 °C(Predicted)
Density 1.136
storage temp. Store at -20°C
solubility Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).
form White to off-white solid
pka 13.57±0.70(Predicted)
color colorless
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
InChIKey QXRSDHAAWVKZLJ-PVYNADRNSA-N
CAS DataBase Reference 152044-54-7

Epothilone B price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) E2656 (−)-Epothilone B from Sorangium cellulosum, ≥98% (HPLC) 152044-54-7 1MG ₹5260.95 2022-06-14 Buy
Sigma-Aldrich(India) E2656 (−)-Epothilone B from Sorangium cellulosum, ≥98% (HPLC) 152044-54-7 5MG ₹15988.53 2022-06-14 Buy
Sigma-Aldrich(India) 325001 Epothilone B, Synthetic A structural analog of Epothilone A with similar biological properties. 152044-54-7 1MG ₹14970 2022-06-14 Buy
TCI Chemicals (India) E1378 Epothilone B 152044-54-7 5MG ₹4800 2022-05-26 Buy
TCI Chemicals (India) E1378 Epothilone B 152044-54-7 25MG ₹22900 2022-05-26 Buy
Product number Packaging Price Buy
E2656 1MG ₹5260.95 Buy
E2656 5MG ₹15988.53 Buy
325001 1MG ₹14970 Buy
E1378 5MG ₹4800 Buy
E1378 25MG ₹22900 Buy

Epothilone B Chemical Properties,Uses,Production

Chemical Properties

White Powder

Uses

Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the chromosomes that will end up in each cell are separated by thin filaments called microtubules. Normally these microtubules then break down as the cell division progresses. This class of cytotoxic chemo drugs prevents that break down and thus prevents cells from completing division.

Definition

ChEBI: An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).

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).

Biological Activity

Microtubule stabilization agent that promotes tubulin polymerization and induces G 2 -M cell cycle arrest (EC 50 = 3 - 92 nM). Potently inhibits a variety of human cancer cell lines (IC 50 values are 0.13 - 0.64 nM), including MDR cells overexpressing the P-glycoprotein efflux pump. Exhibits potent anticancer activity in numerous human tumor xenografts in vivo .

Side effects

Patupilone is naturally occurring epothilone B. The major dose-limiting adverse reaction to patupilone is diarrhea, rather than neuropathy. Other significant adverse reactions include fatigue and nausea. In phase I/II studies, severe diarrhea was reported in 14–19% of patients. Hematological toxicity appears to be minimal. Grade 3 peripheral neuropathy was the dose-limiting adverse reaction in one phase I study, along with grade 3 diarrhea[3].

References

1) Goodin et al. (2004), Epothilones: mechanism of action and biologic activity; J. Clin. Oncol., 22 2015
2) Bollag et al. (1995), Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action; Cancer Res., 55 2325.
3) Lipp, H. and J. Hartmann. “Chapter 45 - Cytostatic and cytotoxic drugs.”Side Effects of Drugs Annual (2011):935-962.

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Epothilone B Spectrum

Epothilone B(EPO906) Epothilone B HOUSE STANDARD Epothilone B(Patupilone) (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-dioxa-bicyclo[14.1.0]heptadecan-5,9-dione Epothilone B (EPO906, Patupilone) EPOTHILONE (1S,3S,7S,10R,11S,12S,16R,E)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione Patupilone (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Epothilone B, >=98% Patupilone(Epothilone B) atupilone (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione ()-Epothilone B,EPO906, EpoB, Patupilone 4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)- EPO 906A Epothilone B Patupilone EPO906, EpoB, Patupilone CS-556 epothilone B 152044-54-7 Epothilone B, ≥98% (HPLC) EPO 906;EPO906;PATUPILONE Patupilone (EPO906, Epothilone B) Paclitaxel Impurity 109 Oncology API Epothilon B Epothilone B USP/EP/BP (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 Ebomycin B 152044-54-7 Chiral Reagents Inhibitors Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds API