TAS-106

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
TAS-106
Accession Number
DB06656
Type
Small Molecule
Groups
Investigational
Description

TAS-106 is a new nucleoside antimetabolite. TAS-106 has demonstrated strong antitumor activity without serious toxicity in nude rat models bearing human tumours 1.

Structure
Thumb
Synonyms
  • 3'-C-Ethynylcytidine
  • 4-Amino-1-((2R,3R,4R,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one
External IDs
TAS 106 / TAS-106
Categories
UNII
Y3O05I09ZK
CAS number
180300-43-0
Weight
Average: 267.241
Monoisotopic: 267.085520531
Chemical Formula
C11H13N3O5
InChI Key
JFIWEPHGRUDAJN-DYUFWOLASA-N
InChI
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
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@](O)(C#C)[C@H]1O

Pharmacology

Indication

Investigated for use/treatment in solid tumors and cancer/tumors (unspecified).

Pharmacodynamics
Not Available
Mechanism of action

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.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Shimamoto Y, Fujioka A, Kazuno H, Murakami Y, Ohshimo H, Kato T, Matsuda A, Sasaki T, Fukushima M: Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. Jpn J Cancer Res. 2001 Mar;92(3):343-51. [PubMed:11267946]
External Links
ChemSpider
154057
ChEMBL
CHEMBL573352

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentMalignancies / Tumors, Solid1
2TerminatedTreatmentHead and Neck Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.47 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.21ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.01 m3·mol-1ChemAxon
Polarizability24.68 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on March 19, 2008 10:45 / Updated on August 02, 2019 07:53