| Identification | Back Directory | [Name]
Rigosertib sodium | [CAS]
592542-60-4 | [Synonyms]
Novonex
ON 01910 Na
ON 01910 sodium
RIGOSERTIB SODIUM
Rigosertib sodium（E）
RIGOSERTIB SODIUM (ON-01910 SODIUM)
Rigosertib sodium - ON01910 sodium | Estybon
ON-01910 SODIUM;ON01910 SODIUM;ON01910 SODIUM
(E)-2,4,6-Trimethoxystyryl 3-[(carboxymethyl)amino]-4-methoxybenzyl sulfone sodium salt
Glycine, N-[2-Methoxy-5-[[[(1E)-2-(2,4,6-triMethoxyphenyl)ethenyl]sulfonyl]Methyl]phenyl]-, sodiuM Slat | [Molecular Formula]
C21H24NNaO8S | [MDL Number]
MFCD11655911 | [MOL File]
592542-60-4.mol | [Molecular Weight]
473.472 |
| Chemical Properties | Back Directory | [Melting point ]
174-178℃ | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Powder | [color ]
White to yellow | [InChI]
1S/C21H25NO8S.Na/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24;/h5-11,22H,12-13H2,1-4H3,(H,23,24);/q;+1/p-1/b8-7+; | [InChIKey]
VLQLUZFVFXYXQE-USRGLUTNSA-M | [SMILES]
[Na+].[S](=O)(=O)(Cc2cc(c(cc2)OC)NCC(=O)[O-])\C=C\c1c(cc(cc1OC)OC)OC |
| Hazard Information | Back Directory | [Uses]
Rigosertib sodium (ON-01910 sodium) is a multi-kinase inhibitor and a selective anti-cancer agent, which induces apoptosis by inhibition the PI3K/Akt pathway, promotes the phosphorylation of histone H2AX and induces G2/M arrest in cell cycle[1][2]. Rigosertib sodium is a selective and non-ATP-competitive inhibitor of PLK1 with an IC50 of 9 nM[3]. | [Definition]
ChEBI: Rigosertib sodium is the sodium salt of rigosertib. It is an anti-cancer agent which has been granted Orphan Drug Designation by the FDA for use in patients with myelodysplastic syndromes (MDS). It has a role as a microtubule-destabilising agent, an antineoplastic agent, an EC 2.7.11.21 (polo kinase) inhibitor and an apoptosis inducer. It contains a rigosertib(1-). | [Biological Activity]
Cell permeable: yes', 'Primary Target
PI 3-K/Akt/mTOR signaling', 'Target IC50: 32, 42, 182, 18 and 155 nM against Bcr-Abl, Flt1, Fyn, PDGFR, and Src, respectively | [in vivo]
Rigosertib (250 mg/kg, i.p.) markedly inhibits tumor growth in mouse xenograft models of Bel-7402, MCF-7, and MIA-PaCa cells[3]. Rigosertib (200 mg/kg, i.p.) shows inhibition on tumor growth in a mouse xengraft model of BT20 cells[4]. | [IC 50]
PLK1: 9 nM (IC50); PLK2: 260 nM (IC50); PDGFR: 18 nM (IC50); Src: 155 nM (IC50); BCR-ABL: 32 nM (IC50); Cdk1: 260 nM (IC50); Flt1: 42 nM (IC50); Fyn: 182 nM (IC50) | [References]
[1] Xu F, et al. Rigosertib as a selective anti-tumor agent can ameliorate multiple dysregulated signalingtransduction pathways in high-grade myelodysplastic syndrome. Sci Rep. 2014 Dec 4;4:7310. DOI:10.1038/srep07310
[2] Hyoda T, et al. Rigosertib induces cell death of a myelodysplastic syndrome-derived cell line by DNA damage-induced G2/M arrest. Cancer Sci. 2015 Mar;106(3):287-93. DOI:10.1111/cas.12605
[3] Gumireddy K, et al. ON01910, a non-ATP-competitive small molecule inhibitor of Plk1, is a potent anticancer agent. Cancer Cell. 2005 Mar;7(3):275-86. DOI:10.1016/j.ccr.2005.02.009
[4] Reddy MV, et al. Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): synthesis, structure-activity relationship, and biological activity. J Med Chem. DOI:10.1021/jm200570p
[5] Chapman CM, et al. ON 01910.Na is selectively cytotoxic for chronic lymphocytic leukemia cells through a dual mechanism of action involving PI3K/AKT inhibition and induction of oxidative stress. Clin Cancer Res. 2012 Apr 1;18(7):1979-91 DOI:10.1158/1078-0432.CCR-11-2113 |
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