Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H12FN3O4 |
| Molecular Weight | 257.2184 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1)[C@H]2[C@H](O)[C@H](O)C(CO)=C2F
InChI
InChIKey=QLLGKCJUPWYJON-HLTSFMKQSA-N
InChI=1S/C10H12FN3O4/c11-6-4(3-15)8(16)9(17)7(6)14-2-1-5(12)13-10(14)18/h1-2,7-9,15-17H,3H2,(H2,12,13,18)/t7-,8-,9+/m1/s1
| Molecular Formula | C10H12FN3O4 |
| Molecular Weight | 257.2184 |
| Charge | 0 |
| Count |
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| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:29:48 UTC 2023
by
admin
on
Sat Dec 16 11:29:48 UTC 2023
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| Record UNII |
0Z4A82I0JO
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| Record Status |
Validated (UNII)
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EU-Orphan Drug |
EU/3/17/1937
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FDA ORPHAN DRUG |
447314
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| Code System | Code | Type | Description | ||
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FLUOROCYCLOPENTENYLCYTOSINE
Created by
admin on Sat Dec 16 11:29:48 UTC 2023 , Edited by admin on Sat Dec 16 11:29:48 UTC 2023
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PRIMARY | MedKoo Cat#: 206092Name: RX-3117CAS#: 865838-26-2Chemical Formula: C10H12FN3O4Exact Mass: 257.08118Molecular Weight: 257.22Elemental Analysis: C, 46.69; H, 4.70; F, 7.39; N, 16.34; O, 24.88 | ||
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DTXSID101113297
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865838-26-2
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100000177397
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147412
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11374
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11242315
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C113444
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0Z4A82I0JO
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FG-08
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
Cytadine analogue RX-3117: An orally available small molecule and nucleoside antimetabolite with potential antineoplastic activity. Upon administration, the cytidine analogue RX-3117 is taken up by cells through a carrier-mediated transporter, phosphorylated by uridine cytidine kinase (UCK) and then further phosphorylated to its diphosphate (RX-DP) and triphosphate forms (RX-TP). The triphosphate form is incorporated into RNA and inhibits RNA synthesis. The diphosphate RX-DP is reduced by ribonucleotide reductase (RR) to dRX-DP its triphosphate form (dRX-TP) is incorporated into DNA. In addition, RX-3117 also inhibits DNA methyltransferase 1 (DNMT1). This eventually leads to cell cycle arrest and the induction of apoptosis. UCK is the rate-limiting enzyme in the pyrimidine-nucleotide salvage pathway. Check for active clinical trials using this agent. (NCI Thesaurus)
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ACTIVE MOIETY |
A novel cytidine analog fluorocyclopentenylcytosine (RX-3117, TV-1360) was characterized for its cytotoxicity in a 59-cell line panel and further characterized for cytotoxicity, metabolism and mechanism of action in 15 additional cancer cell lines, including gemcitabine-resistant variants. In both panels sensitivity varied 75-fold (IC50: 0.4- > 30 .MU.M RX-3117). RX-3117 showed a different sensitivity profile compared to cyclopentenyl-cytosine (CPEC) and azacytidine, substrates for uridine-cytidine-kinase (UCK). Dipyridamole, an inhibitor of the equilibrative-nucleoside-transporter protected against RX-3117. Uridine and cytidine protected against RX-3117, but deoxycytidine (substrate for deoxycytidine-kinase (dCK)) not, although it protected against gemcitabine, demonstrating that RX-3117 is a substrate for UCK and not for dCK. UCK activity was abundant in all cell lines, including the gemcitabine-resistant variants.
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ACTIVE MOIETY |
RX-3117 has shown broad spectrum anti-tumor activity against over 100 different human cancer cell lines and efficacy in 17 different mouse xenograft models. In preclinical mouse xenograft studies, RX-3117 demonstrated superior efficacy to gemcitabine. In addition, RX-3117 retained its full anti-tumor activity in human cancer cell lines made resistant to the anti-tumor effects of gemcitabine, supporting a unique, highly-targeted mechanism of action.
An exploratory Phase I clinical trial of RX-3117 showed that oral administration of a 50 mg dose of RX-3117 achieved oral bioavailability of 56% and a plasma half-life (T1/2) of 14 hours. In addition, RX-3117 appeared to be safe and well tolerated in all subjects throughout the dose range tested.
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