| Identification | Back Directory | [Name]
(-)-EPOTHILONE A | [CAS]
152044-53-6 | [Synonyms]
CS-555
CS-1899
Epothile
Epothilon A
EPOTHILONE A
Epothilone-S
(-)-EPOTHILONE A
Epothilone A USP/EP/BP
Ixabepilone Impurity 5
Ixabepilone Impurity 5 (Epothilone A)
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione,7,11-dihydroxy-8,8,10,12-tetraMethyl-3- [(1E)-1-Methy
(1S,3S,7S,10R,11S,12S,16R,E)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-(1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-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-tetramethyl-3- [(1E)-1-methyl-2-(2-methyl-4-thiazolyl)- ethenyl]-,(1R,3R,7R,10S,11R,12R,16S)-rel-
Epothilone A
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-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-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Epothilone A | [Molecular Formula]
C26H39NO6S | [MDL Number]
MFCD26960884 | [MOL File]
152044-53-6.mol | [Molecular Weight]
493.66 |
| Chemical Properties | Back Directory | [Melting point ]
95℃ | [alpha ]
D21 -47.1° (c = 1.0 in methanol) | [Boiling point ]
683.3±55.0 °C(Predicted) | [density ]
1.143 | [storage temp. ]
?20°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
solid | [pka]
13.57±0.70(Predicted) | [color ]
White to Off-White | [Stability:]
Stable under recommended storage conditions., Stable Under Recommended Storage C | [InChIKey]
HESCAJZNRMSMJG-KKQRBIROSA-N | [SMILES]
[C@]12([H])[C@]([H])(O1)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C1=CSC(C)=N1)C2 |
| Hazard Information | Back Directory | [Uses]
Epothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumor agent. | [Uses]
Epothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumour agent. | [Uses]
The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell. | [Definition]
ChEBI: An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). | [Biological Activity]
epothilone a (epo a) is a naturally occurring microtubule-stabilizing macrolide that was first isolated from the myxobacterium sorangium cellulosum. the ic50 value of epothilone a in hct-116 cell line is 4.4 nm [1].it has been found that the skov-3 human ovarian cancer cells were susceptible to epothilone a with ic50 value of 20.4 ± 1.4 nm [2]. the antiproliferative capacity of epothilone a in skov-3 cell line (measured as ic50 after 72 h continuous treatment) was six times greater than that of ptx’s. besides, epothilone a induced time coursedependent apoptosis and necrosis [2]. | [target]
MDR CCRF-CEM/VBL100 cells | [References]
[1] regueiro-ren a1, borzilleri rm, zheng x, kim sh, johnson ja, fairchild cr, lee fy, long bh, vite gd. synthesis and biological activity of novel epothilone aziridines. org lett. 2001 aug 23;3(17):2693-6.
[2] rogalska a1, marczak a, gajek a, szwed m, ?liwińska a, drzewoski j, jó?wiak z. induction of apoptosis in human ovarian cancer cells by new anticancer compounds, epothilone a and b. toxicol in vitro. 2013 feb;27(1):239-49. |
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