NAV

TAS-106

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

Identification

Generic Name
TAS-106
DrugBank Accession Number
DB06656
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 267.241
Monoisotopic: 267.085520531
Chemical Formula
C11H13N3O5
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
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Y3O05I09ZK
CAS number
180300-43-0
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

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. [Article]
ChemSpider
154057
ChEMBL
CHEMBL573352
ZINC
ZINC000003813525

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentHead And Neck Cancer1
1CompletedTreatmentCancer / Solid Tumors1

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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dr-0920000000-a3ccf4c93cce4c1b3b28
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-1001-2690000000-508d23ab4ac4c916c5c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-3930000000-3ed4d6156f0c82d02284
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03kc-4960000000-3a62582eed29b192d0a3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-8910000000-9d8253b8f4b7dc36bb0c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mp-9310000000-cd68224142342ac14af5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at March 19, 2008 16:45 / Updated at June 12, 2020 16:52