Berzosertib
PubChem CID
59472121
Structure
Molecular Formula
Synonyms
- 1232416-25-9
- VE-822
- Berzosertib
- VX-970
- VE822
Molecular Weight
463.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2012-08-20
- Modify:2025-01-18
Description
3-[3-[4-(methylaminomethyl)phenyl]-5-isoxazolyl]-5-(4-propan-2-ylsulfonylphenyl)-2-pyrazinamine is a sulfonamide.
Berzosertib (VX-970) has been used in trials studying the treatment of Ovarian Neoplasms, Ovarian Serous Tumor, Adult Solid Neoplasm, Advanced Solid Tumor, and Advanced Solid Neoplasm, among others.
Berzosertib is an inhibitor of ataxia telangiectasia and rad3-related (ATR) kinase, a DNA damage response kinase, with potential antineoplastic activity. Upon administration, berzosertib selectively binds to and inhibits ATR kinase activity and prevents ATR-mediated signaling in the ATR-checkpoint kinase 1 (Chk1) signaling pathway. This prevents DNA damage checkpoint activation, disrupts DNA damage repair, and induces tumor cell apoptosis. ATR, a serine/threonine protein kinase upregulated in a variety of cancer cell types, plays a key role in DNA repair, cell cycle progression, and survival; it is activated by DNA damage caused during DNA replication-associated stress.
Chemical Structure Depiction
3-[3-[4-(methylaminomethyl)phenyl]-1,2-oxazol-5-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C24H25N5O3S/c1-15(2)33(30,31)19-10-8-18(9-11-19)21-14-27-24(25)23(28-21)22-12-20(29-32-22)17-6-4-16(5-7-17)13-26-3/h4-12,14-15,26H,13H2,1-3H3,(H2,25,27)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
JZCWLJDSIRUGIN-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC(C)S(=O)(=O)C1=CC=C(C=C1)C2=CN=C(C(=N2)C3=CC(=NO3)C4=CC=C(C=C4)CNC)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C24H25N5O3S
Computed by PubChem 2.2 (PubChem release 2021.10.14)
1232416-25-9
- 2-PYRAZINAMINE, 3-(3-(4-((METHYLAMINO)METHYL)PHENYL)-5-ISOXAZOLYL)-5-(4-((1-METHYLETHYL)SULFONYL)PHENYL)-
- 3-(3-(4-((METHYLAMINO)METHYL)PHENYL)-1,2-OXAZOL-5-YL)-5-(4-(PROPANE-2-SULFONYL)PHENYL)PYRAZIN-2-AMINE
- berzosertib
- VE-822
- VX-970
- 1232416-25-9
- VE-822
- Berzosertib
- VX-970
- VE822
- VX970
- VE 822
- Berzosertib [USAN]
- 5-(4-(isopropylsulfonyl)phenyl)-3-(3-(4-((methylamino)methyl)phenyl)isoxazol-5-yl)pyrazin-2-amine
- MFCD27976794
- 3-(3-{4-[(METHYLAMINO)METHYL]PHENYL}-1,2-OXAZOL-5-YL)-5-[4-(PROPANE-2-SULFONYL)PHENYL]PYRAZIN-2-AMINE
- VE-822 (VX-970)
- L423PRV3V3
- 2-Pyrazinamine, 3-[3-[4-[(methylamino)methyl]phenyl]-5-isoxazolyl]-5-[4-[(1-methylethyl)sulfonyl]phenyl]-
- 3-[3-[4-(methylaminomethyl)phenyl]-1,2-oxazol-5-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine
- M6620
- 2-Pyrazinamine, 3-(3-(4-((methylamino)methyl)phenyl)-5-isoxazolyl)-5-(4-((1-methylethyl)sulfonyl)phenyl)-
- M-6620
- 3-[3-[4-[(Methylamino)methyl]phenyl]-5-isoxazolyl]-5-[4-[(1-methylethyl)sulfonyl]phenyl]-2-pyrazinamine
- BDBM50226746
- 3-(3-(4-((METHYLAMINO)METHYL)PHENYL)-1,2-OXAZOL-5-YL)-5-(4-(PROPANE-2-SULFONYL)PHENYL)PYRAZIN-2-AMINE
- 5-(4-(isopropylsulfonyl)phenyl)-3-(3-(4-((methylamino)methyl)phenyl)isoxazol-5-yl)pyrazin-2-amine.
- UNII-L423PRV3V3
- 3-(3-(4-((Methylamino)methyl)phenyl)-5-isoxazolyl)-5-(4-((1-methylethyl)sulfonyl)phenyl)-2-pyrazinamine
- VX-970;Berzosertib
- BERZOSERTIB [INN]
- Berzosertib (USAN/INN)
- Berzosertib (VE-822)
- AGN-PC-0CXKB3
- VE-822 (Berzosertib)?
- BERZOSERTIB [WHO-DD]
- GTPL8003
- SCHEMBL3061890
- CHEMBL3989870
- EX-A529
- CHEBI:131166
- BDBM350085
- DTXSID601025940
- HMS3653C05
- HMS3747I11
- BCP07948
- NSC777718
- s7102
- US10208027, Compound II-1
- US10208027, Compound II-2
- US10208027, Compound II-3
- US10208027, Compound II-4
- VX 970
- AKOS025404905
- CCG-264673
- CS-1861
- DB11794
- NSC-777718
- SB17265
- NCGC00386313-07
- AC-32951
- AS-17041
- DA-46989
- HY-13902
- SY057018
- NS00073122
- SW220202-1
- D11148
- BRD-K04701033-001-01-3
- BRD-K04701033-001-03-9
- BRD-K04701033-001-04-7
- Q27089129
- 2-Amino-5-[4-(isopropylsulfonyl)phenyl]-3-[3-[4-[(methylamino)methyl]phenyl]-5-isoxazolyl]pyrazine
- 5-(4-isopropylsulfonylphenyl)-3-[3-[4-(methylaminomethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine
- Synthesis of 3-[3-[4-[dideuterio(methylamino)methyl]phenyl]isoxazol-5-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
463.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
463.16781085 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
463.16781085 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
132 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
714
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=JZCWLJDSIRUGIN-UHFFFAOYSA-N
- ChEBI3-[3-[4-(methylaminomethyl)phenyl]-5-isoxazolyl]-5-(4-propan-2-ylsulfonylphenyl)-2-pyrazinaminehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:131166
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useBerzosertibhttps://www.drugbank.ca/drugs/DB11794
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Chemical Probes PortalBERZOSERTIBhttps://www.chemicalprobes.org/berzosertib
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jsp
- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsBERZOSERTIBhttps://www.dgidb.org/drugs/ncit:C116355
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox3-(3-(4-((Methylamino)methyl)phenyl)-5-isoxazolyl)-5-(4-((1-methylethyl)sulfonyl)phenyl)-2-pyrazinaminehttps://comptox.epa.gov/dashboard/DTXSID601025940CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- EU Clinical Trials Register
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- Metabolomics Workbench
- NIPH Clinical Trials Search of Japan
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/3-(3-{4-[(methylamino)methyl]phenyl}-1,2-oxazol-5-yl)-5-[4-(propane-2-sulfonyl)phenyl]pyrazin-2-amineNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/aboutberzosertibhttps://pharos.nih.gov/ligands/BP4GKQ7KU4JT
- Springer Nature
- Wikidataberzosertibhttps://www.wikidata.org/wiki/Q27089129
- WikipediaBerzosertibhttps://en.wikipedia.org/wiki/Berzosertib
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlberzosertibhttps://www.ncbi.nlm.nih.gov/mesh/2006750
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 392221924https://pubchem.ncbi.nlm.nih.gov/substance/392221924
CONTENTS