A microtubule-stabilizing agent
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Epothilone D

Item No. 18765

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-oxacyclohexadec-13-ene-2,6-dione
CAS Number
189453-10-9
Synonyms
  • Desoxyepothilone B
  • NSC 73147
Molecular Formula
C27H41NO5S
Formula Weight
491.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: Soluble
SMILES
C/C([C@H](C/C=C(C)\CCC[C@@H]1C)OC(C[C@H](O)C(C([C@@H]([C@H]1O)C)=O)(C)C)=O)=C\C2=CSC(C)=N2
InChi Code
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
InChi Key
XOZIUKBZLSUILX-GIQCAXHBSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Epothilones are microtubule-stabilizing agents with potential anti-neoplastic actions.1,2,3 They are natural macrolides that have high potency in both taxane-sensitive and taxane-resistant models.2,3 Epothilone D is a desoxy form of epothilone B (Item No. 10924) that inhibits the growth of a variety of cancer cells both in vitro (IC50 values range from 0.97 to 21 nM) and in mice.3,4 Epothilone D is brain penetrant and reduces neurodegeneration in aged tau transgenic mice.5,6 Effects include improved axonal transport, decreased tau neuropathology, and reduced hippocampal neuron loss.5,6 Epothilone D also rescues microtubule defects and attenuates nigrostriatal degeneration in a mouse model of Parkinson’s disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bollag, D.M., McQueney, P.A., Zhu, J., et al. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 55(11), 2325-2333 (1995).

    2. Goodin, S., Kane, M.P., and Rubin, E.H. Epothilones: Mechanism of action and biologic activity. J. Clin. Oncol. 22(10), 2015-2025 (2011).

    3. Cheng, K.L., Bradley, T., and Budman, D.R. Novel microtubule-targeting agents - the epothilones. Biologics 2(4), 789-811 (2008).

    4. Cartelli, D., Casagrande, F., Busceti, C.L., et al. Microtubule alterations occur early in experimental parkinsonism and the microtubule stabilizer epothilone D is neuroprotective. Sci. Rep. 3, (2013).

    5. Brunden, K.R., Zhang, B., Carroll, J., et al. Epothilone D improves microtubule density, axonal integrity, and cognition in a transgenic mouse model of tauopathy. J. Neurosci. 30(41), 13861-13866 (2010).

    6. Lou, K., Yao, Y., Hoye, A.T., et al. Brain-penetrant, orally bioavailable microtubule-stabilizing small molecules are potential candidate therapeutics for Alzheimer’s disease and related tauopathies. J. Med. Chem. 57(14), 6116-6127 (2014).