Epothilone

Epothilones are a class of potential cancer drugs. Like taxanes, they prevent cancer cells from dividing by interfering with tubulin, but in early trials, epothilones have better efficacy and milder adverse effects than taxanes.

Epothilones

Epothilones A (R = H) and B (R = CH3)

Chemical formulae

A: C26H39NO6S
B: C27H41NO6S

Molecular masses

A: 493.66 g/mol
B: 507.68 g/mol

CAS numbers

A: 152044-53-6
B: 152044-54-7

PubChem

A: 448799
B: 448013

Epothilones C (R = H) and D (R = CH3)

Chemical formulae

C: C26H39NO5S
D: C27H41NO5S

Molecular masses

C: 477.66 g/mol
D: 491.68 g/mol

CAS numbers

C: 186692-73-9
D: 189453-10-9

PubChem

C: 9891226
D: 447865

Epothilones E (R = H) and F (R = CH3)

Chemical formulae

E: C26H39NO7S
F: C27H41NO7S

Molecular masses

E: 509.66 g/mol
F: 523.68 g/mol

CAS numbers

E: 201049-37-8
F: 208518-52-9

PubChem

E: 9806341
F: 9914741

Disclaimer and references

Epothilones were originally identified as metabolites produced by the soil-dwelling myxobacterium Sorangium cellulosum.. As of September 2008, epothilones A to F have been identified and characterized.

Early studies in cancer cell lines and human cancer patients indicate superior efficacy to the taxanes. Their mechanism of action is similar, but their chemical structure is simpler. Due to their better water solubility, cremophors (solubilizing agents used for paclitaxel which can affect cardiac function and cause severe hypersensitivity) are not needed. Endotoxin-like properties known from paclitaxel, like activation of macrophages synthesizing inflammatory cytokines and nitric oxide, are not observed for epothilone B.

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