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Epothilone B

Epothilone B Structure
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
MDL Number:
MFCD02101921
MOL File:
152044-54-7.mol
MSDS File:
SDS
Last updated:2024-04-10 11:43:08
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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
NCI Dictionary of Cancer Terms epothilone; epothilone B
FDA UNII UEC0H0URSE
NCI Drug Dictionary patupilone

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09,GHS06
Signal word  Danger
Hazard statements  H310-H341-H360-H372-H315-H317-H410-H300
Precautionary statements  P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P260-P264-P270-P314-P501-P273-P391-P501-P201-P202-P281-P308+P313-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P310-P321-P330-P405-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
WGK Germany  3
HS Code  29419090
NFPA 704
0
4 0

Epothilone B price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E2656 (?)-Epothilone B from Sorangium cellulosum, ≥98% (HPLC) 152044-54-7 1mg $51.7 2024-03-01 Buy
Sigma-Aldrich 325001 Epothilone B, Synthetic 152044-54-7 1mg $162 2023-01-07 Buy
TCI Chemical E1378 Epothilone B 152044-54-7 5MG $98 2024-03-01 Buy
TCI Chemical E1378 Epothilone B 152044-54-7 25MG $335 2024-03-01 Buy
Cayman Chemical 10924 Epothilone B ≥95% 152044-54-7 1mg $109 2024-03-01 Buy
Product number Packaging Price Buy
E2656 1mg $51.7 Buy
325001 1mg $162 Buy
E1378 5MG $98 Buy
E1378 25MG $335 Buy
10924 1mg $109 Buy

Epothilone B Chemical Properties,Uses,Production

Description

Epothilone B (152044-54-7) induces microtubule polymerization. Causes cell cycle arrest at the G2-M transition (EC50 = 32 nM for HeLa cells). Induces apoptosis. Cell permeable.

Chemical Properties

White Powder

Uses

Epothilone B (Epo B) is a macrolide that causes the formation of bundles of intracellular microtubules in non-mitotic cells, induces the formation of hyperstable tubulin polymers, and arrests cell cycling in mitosis. It induces mitotic arrest at the G2-M transition in Hs578T and HeLa cells (IC50 = 3 and 32 nM, respectively) as well as in multidrug resistant KB3-1 and KBV-1 cells (IC50 = 16 and 92 nM, respectively). Epo B causes cell cycle arrest at nanomolar IC50 values in cell lines from ovarian, breast, lung, colon, prostate, and squamous cancer.

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.

Uses

Epothilone B is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Like epothilone A, epothilone B acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity.

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 .

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).

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.

Epothilone B synthesis

595558-95-5
152044-54-7
Synthesis of Epothilone B from 4,17-Dioxabicyclo[14.1.0]heptadec-13-ene-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,13E,16R)-

Epothilone B Preparation Products And Raw materials

Raw materials

2-Propenal, 2-methyl-3-(2-methyl-4-thiazolyl)-, (2E)- 187283-44-9 2,2-dimethyl-3-oxopentanal Epothilone D (4S,7R,8S,9S,13Z,16S)-4,8-Bis-{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxocyclohexadec-13-ene-2,6-dione
4-FORMYL-2-METHYLTHIAZOLE

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Preparation Products

IXABEPILONE

Epothilone B Suppliers

Global( 289)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai Minbiotech Co., Ltd.
+8617315815539 sales@minbiotech.com CHINA 129 58
Hebei Mojin Biotechnology Co., Ltd 		+8613288715578 sales@hbmojin.com China 12456 58
Hangzhou ICH Biofarm Co., Ltd 		+undefined8613073685410 sales@ichemie.com China 985 58
Shaanxi Haibo Biotechnology Co., Ltd 		+undefined18602966907 qinhe02@xaltbio.com China 1000 58
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Hebei Guanlang Biotechnology Co., Ltd. 		+86-19930503282 alice@crovellbio.com China 8823 58
Xiamen AmoyChem Co., Ltd 		+86-592-6051114 +8618959220845 sales@amoychem.com China 6387 58
Supplier Advantage
Shanghai Minbiotech Co., Ltd.
58
Hebei Mojin Biotechnology Co., Ltd 		58
Hangzhou ICH Biofarm Co., Ltd 		58
Shaanxi Haibo Biotechnology Co., Ltd 		58
Henan Tianfu Chemical Co.,Ltd. 		55
ATK CHEMICAL COMPANY LIMITED 		60
career henan chemical co 		58
Hubei Jusheng Technology Co.,Ltd. 		58
Hebei Guanlang Biotechnology Co., Ltd. 		58
Xiamen AmoyChem Co., Ltd 		58

Related articles

View Lastest Price from Epothilone B manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Epothilone B pictures 2024-04-12 Epothilone B
152044-54-7
 US $0.00 / kg 1kg 99% 2000ton Shaanxi Haibo Biotechnology Co., Ltd
Epothilone B pictures 2024-03-16 Epothilone B
152044-54-7
 US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Epothilone B pictures 2023-11-01 Epothilone B
152044-54-7
 US $0.00-0.00 / kg 1kg 99.9% 20 tons Hangzhou ICH Biofarm Co., Ltd
  • Epothilone B pictures
  • Epothilone B
    152044-54-7
  • US $0.00 / kg
  • 99%
  • Shaanxi Haibo Biotechnology Co., Ltd
  • Epothilone B pictures
  • Epothilone B
    152044-54-7
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Epothilone B pictures
  • Epothilone B
    152044-54-7
  • US $0.00-0.00 / kg
  • 99.9%
  • Hangzhou ICH Biofarm Co., Ltd

Epothilone B Spectrum

Epothilone B(152044-54-7)1HNMR

152044-54-7(Epothilone B)Related Search:

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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