U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H11F3N2OS
Molecular Weight 312.31
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XAV-939

SMILES

FC(F)(F)C1=CC=C(C=C1)C2=NC(=O)C3=C(CCSC3)N2

InChI

InChIKey=KLGQSVMIPOVQAX-UHFFFAOYSA-N
InChI=1S/C14H11F3N2OS/c15-14(16,17)9-3-1-8(2-4-9)12-18-11-5-6-21-7-10(11)13(20)19-12/h1-4H,5-7H2,(H,18,19,20)

HIDE SMILES / InChI

Molecular Formula C14H11F3N2OS
Molecular Weight 312.31
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

XAV-939 was discovered as a selectively inhibitor of Wnt/β-catenin-mediated transcription through tankyrase1/2 inhibition, regulates axin levels and does not affect CRE, NF-κB or TGF-β. Wnt/b-catenin pathway has been implicated in many cancers.

Originator

Curator's Comment: # Novartis Institutes for Biomedical Research

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [IC50]
4.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
SH-SY5Y cells, was inhibited by XAV939. XAV939 treatment led to the reduction of β-catenin within the cells, confirming its inhibitory effect of WNT. The inhibition of WNT signaling by XAV939 did not affect cell morphology, survival, and proliferation; however, the differentiation and sensitivity to anticancer drugs of human neuroblastoma cells were altered. The treatment of XAV939 resulted in the downregulation of mature neuronal markers, including β-tubulin III, PHOX2A, and PHOX2B, whereas neural progenitor markers (PAX6, TFAP2α, and SLUG) were upregulated.
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:19:51 GMT 2023
Edited
by admin
on Sat Dec 16 20:19:51 GMT 2023
Record UNII
G2MY39VR77
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XAV-939
Code English
2-(4-(Trifluoromethyl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-4-ol
Systematic Name English
3,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one
Systematic Name English
NVP-XAV 939
Code English
2-[4-(Trifluoromethyl)phenyl]-5H,7H,8H-thiopyrano[4,3-d]pyrimidin-4-ol
Common Name English
4H-Thiopyrano[4,3-d]pyrimidin-4-one, 3,5,7,8-tetrahydro-2-[4-(trifluoromethyl)phenyl]-
Systematic Name English
XAV939
Code English
Code System Code Type Description
CAS
284028-89-3
Created by admin on Sat Dec 16 20:19:52 GMT 2023 , Edited by admin on Sat Dec 16 20:19:52 GMT 2023
PRIMARY
FDA UNII
G2MY39VR77
Created by admin on Sat Dec 16 20:19:52 GMT 2023 , Edited by admin on Sat Dec 16 20:19:52 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY