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
| Molecular Formula | C11H13N3O5 |
| Molecular Weight | 267.238 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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) |
|||
Target ID: P24928 Gene ID: 5430.0 Gene Symbol: POLR2A Target Organism: Homo sapiens (Human) |
|||
Target ID: O14802 Gene ID: 11128.0 Gene Symbol: POLR3A Target Organism: Homo sapiens (Human) |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and in vitro activities of new anticancer duplex drugs linking 2'-deoxy-5-fluorouridine (5-FdU) with 3'-C-ethynylcytidine (ECyd) via a phosphodiester bonding. | 2009-10-01 |
|
| PK-PD modeling of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and the enhanced antitumor effect of its phospholipid derivatives in long-circulating liposomes. | 2009-07-30 |
|
| 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. | 2009-05 |
|
| Role of RNase L in apoptosis induced by 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. | 2009-04 |
|
| Inhibition of HIF-1alpha by the anticancer drug TAS106 enhances X-ray-induced apoptosis in vitro and in vivo. | 2008-11-04 |
|
| Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy. | 2008 |
|
| Cellular localization and functional characterization of the equilibrative nucleoside transporters of antitumor nucleosides. | 2007-10 |
|
| Mechanism of action of a new antitumor ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106), differs from that of 5-fluorouracil. | 2007-06 |
|
| Treatment combining X-irradiation and a ribonucleoside anticancer drug, TAS106, effectively suppresses the growth of tumor cells transplanted in mice. | 2007-05-01 |
|
| An apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis mediated by RNase L. | 2006 |
|
| X irradiation induces the proapoptotic state independent of the loss of clonogenic ability in Chinese hamster V79 cells. | 2005-07 |
|
| Possible antitumor activity of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106) against an established gemcitabine (dFdCyd)-resistant human pancreatic cancer cell line. | 2005-05 |
|
| Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). | 2005-04-01 |
|
| Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). | 2005-02-15 |
|
| Synthesis and biological evaluation of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3'-C-ethynylcytidine (ECyd). | 2005 |
|
| A novel anticancer ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, enhances radiation-induced cell death in tumor cells. | 2004-12 |
|
| Synthesis of the cyclic and acyclic acetal derivatives of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, a potent antitumor nucleoside. Design of prodrugs to be selectively activated in tumor tissues via the bio-reduction-hydrolysis mechanism. | 2003-05-29 |
|
| Determination of 3'-C-ethynylcytidine in human plasma and urine by liquid chromatographic-electrospray ionization tandem mass spectrometry. | 2003-02-05 |
|
| Sensitivity of human cancer cells to the new anticancer ribo-nucleoside TAS-106 is correlated with expression of uridine-cytidine kinase 2. | 2002-07 |
|
| Cellular and biochemical mechanisms of the resistance of human cancer cells to a new anticancer ribo-nucleoside, TAS-106. | 2002-04 |
|
| Anticancer mechanisms of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl) cytosine (ECyd, TAS-106). | 2002 |
|
| 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106)1: antitumor effect and mechanism of action. | 2001-09-21 |
|
| Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells. | 2001-09 |
|
| Improvement in precision of the liquid chromatographic-electrospray ionization tandem mass spectrometric analysis of 3'-C-ethynylcytidine in rat plasma. | 2001-04-15 |
|
| Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. | 2001-03 |
|
| Anticancer molecular mechanism of 3'-ethynylcytidine (ECyd). | 2001 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:20 GMT 2025
by
admin
on
Mon Mar 31 18:32:20 GMT 2025
|
| Record UNII |
Y3O05I09ZK
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C1557
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DB06656
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY | |||
|
180300-43-0
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY | |||
|
C29475
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY | |||
|
Y3O05I09ZK
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY | |||
|
176885
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY | |||
|
DTXSID30939319
Created by
admin on Mon Mar 31 18:32:20 GMT 2025 , Edited by admin on Mon Mar 31 18:32:20 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
