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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H15ClN6OS2.CH4O3S
Molecular Weight 527.04
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SNS-314 MESYLATE

SMILES

CS(O)(=O)=O.ClC1=CC=CC(NC(=O)NC2=NC=C(CCNC3=C4SC=CC4=NC=N3)S2)=C1

InChI

InChIKey=FYCODPVDEFFWSR-UHFFFAOYSA-N
InChI=1S/C18H15ClN6OS2.CH4O3S/c19-11-2-1-3-12(8-11)24-17(26)25-18-21-9-13(28-18)4-6-20-16-15-14(5-7-27-15)22-10-23-16;1-5(2,3)4/h1-3,5,7-10H,4,6H2,(H,20,22,23)(H2,21,24,25,26);1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H15ClN6OS2
Molecular Weight 430.934
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

SNS 314 is a selective small molecule inhibitor of Aurora kinases A, B and C. The compound was being developed by Sunesis Pharmaceuticals for the treatment of cancer. Proliferating cells treated with SNS-314 bypass the mitotic spindle checkpoint and fail to undergo cytokinesis, leading to multiple rounds of endoreduplication and eventually cell death. SNS-314 inhibits tumor growth in a variety of preclinical models, and it was being tested in single agent Phase 1 studies in patients with advanced solid tumours.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O14965
Gene ID: 6790.0
Gene Symbol: AURKA
Target Organism: Homo sapiens (Human)
9.0 nM [IC50]
Target ID: Q96GD4|||O60446
Gene ID: 9212.0
Gene Symbol: AURKB
Target Organism: Homo sapiens (Human)
31.0 nM [IC50]
Target ID: Q9UQB9
Gene ID: 6795.0
Gene Symbol: AURKC
Target Organism: Homo sapiens (Human)
3.4 nM [IC50]
Target ID: P04629|||Q7Z5C3
Gene ID: 4914.0
Gene Symbol: NTRK1
Target Organism: Homo sapiens (Human)
12.0 nM [IC50]
Target ID: Q16620
Gene ID: 4915.0
Gene Symbol: NTRK2
Target Organism: Homo sapiens (Human)
5.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Discovery of a potent and selective aurora kinase inhibitor.
2008 Sep 1
SNS-314, a pan-Aurora kinase inhibitor, shows potent anti-tumor activity and dosing flexibility in vivo.
2010 Mar
Targeting high Aurora kinases expression as an innovative therapy for hepatocellular carcinoma.
2017 Apr 25
Patents

Patents

Sample Use Guides

Mice: In the HCT116 human colon cancer xenograft model, administration of 50 and 100 mg/kg SNS-314 led to dose-dependent inhibition of histone H3 phosphorylation for at least 10 h, indicating effective Aurora-B inhibition in vivo.
Route of Administration: Intraperitoneal
SNS-314 Mesylate is a potent and selective inhibitor of Aurora A, Aurora B and Aurora C with IC50 of 9 nM, 31 nM, and 3 nM, respectively and less potent to Trk A/B, Flt4, Fms, Axl, c-Raf and DDR2.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:45:33 UTC 2023
Edited
by admin
on Wed Jul 05 23:45:33 UTC 2023
Record UNII
KGW32FDY3U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SNS-314 MESYLATE
Common Name English
UREA, N-(3-CHLOROPHENYL)-N'-(5-(2-(THIENO(3,2-D)PYRIMIDIN-4-YLAMINO)ETHYL)-2-THIAZOLYL)-, METHANESULFONATE (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID10648376
Created by admin on Wed Jul 05 23:45:33 UTC 2023 , Edited by admin on Wed Jul 05 23:45:33 UTC 2023
PRIMARY
DRUG BANK
DBSALT002371
Created by admin on Wed Jul 05 23:45:33 UTC 2023 , Edited by admin on Wed Jul 05 23:45:33 UTC 2023
PRIMARY
PUBCHEM
24995523
Created by admin on Wed Jul 05 23:45:33 UTC 2023 , Edited by admin on Wed Jul 05 23:45:33 UTC 2023
PRIMARY
CAS
1146618-41-8
Created by admin on Wed Jul 05 23:45:33 UTC 2023 , Edited by admin on Wed Jul 05 23:45:33 UTC 2023
PRIMARY
FDA UNII
KGW32FDY3U
Created by admin on Wed Jul 05 23:45:33 UTC 2023 , Edited by admin on Wed Jul 05 23:45:33 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY