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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25NO8S
Molecular Weight 451.49
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RIGOSERTIB

SMILES

COC1=CC(OC)=C(\C=C\S(=O)(=O)CC2=CC=C(OC)C(NCC(O)=O)=C2)C(OC)=C1

InChI

InChIKey=OWBFCJROIKNMGD-BQYQJAHWSA-N
InChI=1S/C21H25NO8S/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24/h5-11,22H,12-13H2,1-4H3,(H,23,24)/b8-7+

HIDE SMILES / InChI

Molecular Formula C21H25NO8S
Molecular Weight 451.49
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Rigosertib sodium (ON 01910.Na) is a small molecule inhibitor of critical pathways important in the growth and survival of cancer cells, being developed by Onconova Therapeutics ("Onconova") for the treatment of hematologic malignancies and solid tumors. Rigosertib (ON-01910) is a non-ATP-competitive inhibitor of PLK1 with IC50 of 9 nM in a cell-free assay. It shows 30-fold greater selectivity against Plk2 and no activity to Plk3. Extensive Phase I and Phase II studies with rigosertib have been conducted at leading institutions in the U.S. and abroad in more than 450 patients with solid tumors and hematological cancers, including MDS and AML. MDS and AML are blood disorders widely recognized as difficult to manage, with limited therapeutic options available for patients, especially those with drug-resistant disease. The multi-site Phase III ONTIME trial in MDS patients is under a Special Protocol Assessment (SPA) from the U.S. FDA and is being supported by an award from the Therapeutics Acceleration Program (TAP) of the Leukemia and Lymphoma Society (LLS). FDA has granted Orphan Drug Designation for the use of rigosertib in MDS. The clinical program in solid tumors is also advancing with initiation of the Phase II/III combination ONTRAC trial (ON 01910.Na TRial in Patients with Advanced Pancreatic Cancer) and Phase II single agent trial in ovarian cancer. In Japan, SymBio is developing rigosertib for the treatment of refractory/relapsed HR-MDS (IV form) and first-line LR-MDS (oral form).

Approval Year

PubMed

PubMed

TitleDatePubMed
BI 2536, a potent and selective inhibitor of polo-like kinase 1, inhibits tumor growth in vivo.
2007 Feb 20
Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): synthesis, structure-activity relationship, and biological activity.
2011 Sep 22
In vitro antitumor mechanism of (E)-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)methanesulfonamide.
2015 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Rigosertib sodium will be administered as a 72-hr continuous intravenous infusion consisting of 3 consecutive doses of 1800 mg over 24 hours on Days 1, 2, and 3 of a 14-day cycle for the first 8 cycles and then on Days 1, 2, and 3 of a 28-day cycle for the following cycles.
Route of Administration: Intravenous
In Vitro Use Guide
Rigosertib sodium shows cell killing activity against 94 different tumor cell lines with IC50 of 50-250 nM, including BT27, MCF-7, DU145, PC3, U87, A549, H187, RF1, HCT15, SW480, and KB cells. In HeLa cells, Rigosertib sodium (100-250 nM) induces spindle abnormalities and apoptosis.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:26:39 UTC 2019
Edited
by admin
on Mon Oct 21 23:26:39 UTC 2019
Record UNII
67DOW7F9GL
Record Status Validated (UNII)
Record Version
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Name Type Language
RIGOSERTIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
RIGOSERTIB [WHO-DD]
Common Name English
RIGOSERTIB [INN]
Common Name English
N-(2-METHOXY-5-((((1E)-2-(2,4,6-TRIMETHOXYPHENYL)ETHENYL)SULFONYL)METHYL)PHENYL)GLYCINE
Systematic Name English
ON 01910
Code English
RIGOSERTIB [USAN]
Common Name English
ON-01910
Code English
Classification Tree Code System Code
NCI_THESAURUS C1404
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
FDA ORPHAN DRUG 333611
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
FDA ORPHAN DRUG 366412
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
FDA ORPHAN DRUG 289409
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
Code System Code Type Description
CAS
592542-59-1
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
PUBCHEM
6918736
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
WIKIPEDIA
RIGOSERTIB
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
INN
9516
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
EPA CompTox
592542-59-1
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
EVMPD
SUB36359
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
NCI_THESAURUS
C152216
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL1241855
Created by admin on Mon Oct 21 23:26:39 UTC 2019 , Edited by admin on Mon Oct 21 23:26:39 UTC 2019
PRIMARY
Related Record Type Details
ACTIVE MOIETY