Details of the Drug

General Information of Drug (ID: DMOSTXF)

Drug Name
Rigosertib
Synonyms
Rigosertib; 592542-59-1; UNII-67DOW7F9GL; 67DOW7F9GL; N-[2-Methoxy-5-({[(E)-2-(2,4,6-Trimethoxyphenyl)ethenyl]sulfonyl}methyl)phenyl]glycine; ON-01910.Na; Rigosertib [USAN:INN]; 6FS; Rigosertib (USAN); AC1OCFT5; SCHEMBL498624; Estybon (proposed trade name); SCHEMBL498623; GTPL7833; CHEMBL1241855; ON01910.Na; DTXSID30207984; CHEBI:124939; OWBFCJROIKNMGD-BQYQJAHWSA-N; 1910 Na; ZINC3942646; BCP08296; BDBM50060917; 4006AH; AKOS015966442; DB12146; SB16468; (E)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetic a
Indication
Disease Entry ICD 11 Status REF
Myelodysplastic syndrome 2A37 Phase 3 [1]
Solid tumour/cancer 2A00-2F9Z Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 451.5
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C21H25NO8S
IUPAC Name
2-[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]anilino]acetic acid
Canonical SMILES
COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)NCC(=O)O
InChI
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+
InChIKey
OWBFCJROIKNMGD-BQYQJAHWSA-N
Cross-matching ID
PubChem CID
6918736
ChEBI ID
CHEMBL1241855
CAS Number
592542-59-1
UNII
67DOW7F9GL
DrugBank ID
DB12146
TTD ID
D0KF9Q
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
PI3-kinase gamma (PIK3CG) TTHBTOP PK3CG_HUMAN Modulator [3]
Polo-like kinase 1 (PLK1) TTIYVQP PLK1_HUMAN Modulator [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
2'-5'-oligoadenylate synthase 1 (OAS1) OT8ZLOCY OAS1_HUMAN Gene/Protein Processing [4]
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B) OTOA8WU2 PDE4B_HUMAN Gene/Protein Processing [4]
Actin, cytoplasmic 1 (ACTB) OT1MCP2F ACTB_HUMAN Gene/Protein Processing [4]
Actin, cytoplasmic 2 (ACTG1) OTH4V7VQ ACTG_HUMAN Gene/Protein Processing [4]
ADP-ribosylation factor-binding protein GGA2 (GGA2) OT43HO27 GGA2_HUMAN Gene/Protein Processing [4]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [5]
Astrocytic phosphoprotein PEA-15 (PEA15) OTKCKTSX PEA15_HUMAN Gene/Protein Processing [4]
B-cell differentiation antigen CD72 (CD72) OTPOJID2 CD72_HUMAN Gene/Protein Processing [4]
Bcl-2-associated transcription factor 1 (BCLAF1) OT7T8H6A BCLF1_HUMAN Gene/Protein Processing [4]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Myelodysplastic syndrome
ICD Disease Classification 2A37
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
PI3-kinase gamma (PIK3CG) DTT PIK3CG 1.98E-01 -0.05 -0.55
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7833).
3 Phase I study of oral rigosertib (ON 01910.Na), a dual inhibitor of the PI3K and Plk1 pathways, in adult patients with advanced solid malignancies. Clin Cancer Res. 2014 Mar 15;20(6):1656-65.
4 ON 01910.Na is selectively cytotoxic for chronic lymphocytic leukemia cells through a dual mechanism of action involving PI3K/AKT inhibition and induction of oxidative stress. Clin Cancer Res. 2012 Apr 1;18(7):1979-91. doi: 10.1158/1078-0432.CCR-11-2113. Epub 2012 Feb 20.
5 Discontinuous drug binding to proteins: binding of an antineoplastic benzyl styryl sulfone to albumin and enzymes in vitro and in phase I clinical trials. Drug Metab Dispos. 2010 Sep;38(9):1480-5. doi: 10.1124/dmd.110.033001. Epub 2010 May 25.
6 Styryl sulfonyl compounds inhibit translation of cyclin D1 in mantle cell lymphoma cells. Oncogene. 2009 Mar 26;28(12):1518-28. doi: 10.1038/onc.2008.502. Epub 2009 Feb 9.