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RX-3117 — Datasheet

CAT. NO. DC7762

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Parameter	Value
Chemical Name	RX-3117
CAS No.	865838-26-2
Synonyms	RX-3117;4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone (ACI);4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1H)-one;Roducitabine;RX 3117;UNII-0Z4A82I0JO;RX3117;Cytidine Analog RX-3117;4-Amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone;4-amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-cyclopent-2-en-1-yl)-pyrimidin-2(1H)-one;fluorocyclopentenylcytosine;MS-23620;4-Amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)pyrimidin-2(1H)-one;SCHEMBL4409591;BRD-K66213167-001-01-2;Roducitabine [USAN];NSC785657;4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL)CYCLOPENT-2-EN-1-YL)PYRIMIDIN-2-ONE;4-Amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-2(1H)-pyrimidinone;865838-26-2;4-amino-1-((1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)-1,2-dihydropyrimidin-2-one;fluorocyclopentenyl-cytosine;NSC-785657;QLLGKCJUPWYJON-HLTSFMKQSA-N;4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-1,2-dihydropyrimidin-2-one;4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL) CYCLOPENT-2-EN-1-YL) PYRIMIDIN-2-ONE;TV-1360;RODUCITABINE [INN];WHO 11374;0Z4A82I0JO;S900007480;AKOS027327327;NCGC00485875-02;EX-A4776;CHEMBL2064455;fluorocyclopentenyl cytosine;NCGC00485875-01;1-[(1S,4R,5S)-2-Fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl]cytosine;1-((1S,4R,5S)-2-fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl)cytosine;DTXSID101113297;CS-3947;Roducitabine (USAN);AC-35336;HY-15228;CHEBI:147412;2(1H)-PYRIMIDINONE, 4-AMINO-1-((1S,4R,5S)-2-FLUORO-4,5-DIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOPENTEN-1-YL)-;4-amino-1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2-one
Formula	C10H12FN3O4
M.Wt	257.218385696411
SMILES	FC1=C(CO)[C@@H](O)[C@@H](O)[C@@H]1N1C=CC(N)=NC1=O
Purity	>98%
Storage	2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

Biological Activity

RX-3117(TV-1360; Fluorocyclopentenylcytosine) is novel a cytidine analog; shows anticancer activity in several cancer cell lines, including gemcitabine-resistant variants.

In Vitro

RX-3117 showed a different sensitivity profile compared to cyclopentenyl-cytosine (CPEC) and azacytidine, substrates for uridine-cytidine-kinase (UCK).RX-3117 was a very poor substrate for cytidine deaminase (66,000-fold less than gemcitabine). In sensitive U937 cells 1 μM RX-3117 resulted in 90% inhibition of RNA synthesis but 100 μM RX-3117 was required in A2780 and CCRF-CEM cells. RX-3117 at IC50 values did not affect the integrity of RNA [1].

In Vivo

Orally-administered RX-3117 was examined in 9 different human tumor xenograft models (colon, non-small cell lung, small cell lung, pancreatic, renal and cervical), grown subcutaneously in athymic nude mice. In the Colo 205, H460, H69 and CaSki models, gemcitabine treatment resulted in 28%, 30%, 25% and 0% tumor growth inhibition (TGI), respectively, whereas oral treatment with RX-3117 induced 100%, 78%, 62% and 66% TGI, respectively [2].

Target

IC50 value: 0.4- >30 nM (15 cancer cell lines) [1]Target: cytidine analog

References & source

[1]. Peters GJ, et al. Metabolism, mechanism of action and sensitivity profile of fluorocyclopentenylcytosine (RX-3117; TV-1360). Invest New Drugs. 2013 Dec;31(6):1444-57.

[2]. Yang MY, et al. A novel cytidine analog, RX-3117, shows potent efficacy in xenograft models, even in tumors that are resistant to gemcitabine. Anticancer Res. 2014 Dec;34(12):6951-9.

DC Chemicals original product information

Published experimental findings depend on the model and assay conditions. They do not guarantee equivalent performance in every application. For laboratory research use only.