CAS 152044-54-7

Epothilone B

Description:

Epothilone B is a natural product and a member of the epothilone family, which are macrocyclic compounds known for their ability to stabilize microtubules, similar to the mechanism of action of taxanes like paclitaxel. It is derived from the myxobacterium Sorangium cellulosum and exhibits significant antitumor activity, making it a subject of interest in cancer research. The compound has a complex structure characterized by a 16-membered macrolide ring and multiple stereocenters, contributing to its biological activity. Epothilone B is soluble in organic solvents but has limited solubility in water, which can affect its bioavailability. Its mechanism involves binding to the β-tubulin subunit of microtubules, leading to cell cycle arrest and apoptosis in cancer cells. Due to its promising therapeutic potential, epothilone B has been investigated in clinical trials, particularly for treating various types of cancer, including breast cancer and non-small cell lung cancer. However, its clinical use is often limited by its pharmacokinetic properties and the development of resistance in tumor cells.

Formula: C₂₇H₄₁NO₆S

InChI: 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: InChIKey=QXRSDHAAWVKZLJ-PVYNADRNSA-N

SMILES: C[C@@]12[C@@](O1)(C[C@@H](\C(=C\C=3N=C(C)SC3)\C)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC2)[H]

Synonyms:

• (1S,3S,7R,10S,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• (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
• (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
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• 4,17-Dioxabicyclo[14.1.0]heptadecane-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)-
• 4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, [1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-
• Epo 906
• Epo 906A
• Epo B
• Patupilone
• [1S-[1R*, 3R* (E) , 7R*, 10S*, 11R*, 12R*, 16S*]]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl) ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• (-)-Epothilone B

(-)-Epothilone B

CAS: 152044-54-7

Formula: C₂₇H₄₁NO₆S

Molecular weight: 507.68

Ref: 7W-GK5130

Patupilone (Epothilone B)

CAS: 152044-54-7

Formula: C₂₇H₄₁NO₆S

Color and Shape: White To Off-White Solid

Molecular weight: 507.69

Ref: 4Z-P-214001

Epothilone B

CAS: 152044-54-7

Epothilone B

Purity: 98%

Molecular weight: 507.68g/mol

Ref: 54-OR1013109

Epothilone B

CAS: 152044-54-7

Epothilone B

Purity: ≥98%

Molecular weight: 507.68g/mol

Ref: 54-BUP04148

Epothilone B

CAS: 152044-54-7

Formula: C₂₇H₄₁NO₆S

Purity: >95.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 507.69

Ref: 3B-E1378

Epothilone B

CAS: 152044-54-7

Epothilone B (EPO 906) is a compound isolated from the myxobacterium Sorangium cellulosum.

Formula: C₂₇H₄₁NO₆S

Purity: 99.79% - 99.84%

Color and Shape: White Powder

Molecular weight: 507.68

Ref: TM-T6075

Epothilone B (synthetic)

Controlled Product

CAS: 152044-54-7

Applications 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.
References Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995), Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (2001), Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)

Formula: C₂₇H₄₁NO₆S

Color and Shape: Neat

Molecular weight: 507.68

Ref: TR-E588990

Epothilone B-d3 (synthetic)

Controlled Product

CAS: 152044-54-7

Formula: C₂₇D₃H₃₈NO₆S

Color and Shape: White To Off-White

Molecular weight: 510.701

Ref: TR-E588992