Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H13N3O5 |
| Molecular Weight | 267.238 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@](O)(C#C)[C@H]2O
InChI
InChIKey=JFIWEPHGRUDAJN-DYUFWOLASA-N
InChI=1S/C11H13N3O5/c1-2-11(18)6(5-15)19-9(8(11)16)14-4-3-7(12)13-10(14)17/h1,3-4,6,8-9,15-16,18H,5H2,(H2,12,13,17)/t6-,8+,9-,11-/m1/s1
3'-C-ethynylcytidine (Ethynylcytidine, TAS-106) is a synthetic cytidine nucleoside containing a covalently bound ethynyl group with potential antineoplastic and radiosensitizing activities. 3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule. Development of a cytosine derivative of 3'-ethynyl ribonucleoside, TAS-106, as an intravenously administered treatment for solid tumours was discontinued. A phase II trial in patients with head and neck cancer was terminated in the US.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O95602 Gene ID: 25885.0 Gene Symbol: POLR1A Target Organism: Homo sapiens (Human) |
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Target ID: P24928 Gene ID: 5430.0 Gene Symbol: POLR2A Target Organism: Homo sapiens (Human) |
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Target ID: O14802 Gene ID: 11128.0 Gene Symbol: POLR3A Target Organism: Homo sapiens (Human) |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sensitivity of human cancer cells to the new anticancer ribo-nucleoside TAS-106 is correlated with expression of uridine-cytidine kinase 2. | 2002 Jul |
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| An apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis mediated by RNase L. | 2006 |
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| Inhibition of HIF-1alpha by the anticancer drug TAS106 enhances X-ray-induced apoptosis in vitro and in vivo. | 2008 Nov 4 |
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| Role of RNase L in apoptosis induced by 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. | 2009 Apr |
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| 1-(3-C-Ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106), a novel potent inhibitor of RNA polymerase, potentiates the cytotoxicity of CDDP in human cancer cells both in vitro and in vivo. | 2009 May |
Sample Use Guides
Thirty patients were treated with 66 courses of TAS-106 at eight dose levels ranging from 0.67-9.46 mg/m(2). A cumulative sensory peripheral neuropathy was the principal dose-limiting toxicity (DLT) of TAS-106 at the 6.31 mg/m(2) dose level, which was determined to be the maximum tolerated dose (MTD). The recommended phase II dose of TAS-106 is 4.21 mg/m(2).
Route of Administration:
Intravenous
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C1557
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DB06656
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180300-43-0
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C29475
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Y3O05I09ZK
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176885
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ACTIVE MOIETY
