An official website of the United States government

Pimodivir

PubChem CID
67286591
Structure
Pimodivir_small.png
Pimodivir_3D_Structure.png
Molecular Formula
Synonyms
  • Pimodivir
  • 1629869-44-8
  • VX-787
  • Pimodivir [USAN]
  • JNJ872
Molecular Weight
399.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2012-11-30
  • Modify:
    2025-01-18
Description
Pimodivir is under investigation in clinical trial NCT02658825 (A Study to Evaluate the Effect of JNJ-63623872 on Cardiac Repolarization Interval in Healthy Participants).
Pimodivir is an orally bioavailable non-nucleoside inhibitor of the polymerase basic protein 2 (PB2) subunit of the influenza A virus polymerase complex with potential antiviral activity. Upon administration, pimodivir occupies the 7-methyl GTP (m7GTP) binding site of PB2, thereby blocking the cap-snatching activity of the influenza polymerase complex and inhibiting the synthesis of viral mRNA. PB2 is one of three subunits that make up the influenza A viral polymerase complex, which is responsible for replication and transcription of the viral RNA (vRNA) genome in the nuclei of infected cells.
PIMODIVIR is a small molecule drug with a maximum clinical trial phase of III (across all indications) and has 3 investigational indications.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pimodivir.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C20H19F2N5O2/c21-11-5-12-13(7-24-17(12)23-6-11)18-25-8-14(22)19(27-18)26-16-10-3-1-9(2-4-10)15(16)20(28)29/h5-10,15-16H,1-4H2,(H,23,24)(H,28,29)(H,25,26,27)/t9?,10?,15-,16-/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

JGPXDNKSIXAZEQ-SBBZOCNPSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1CC2CCC1[C@@H]([C@H]2NC3=NC(=NC=C3F)C4=CNC5=C4C=C(C=N5)F)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H19F2N5O2
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

1629869-44-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (2S,3S)-3-((5-Fluoro-2-(5-fluoro-1H-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)bicyclo(2.2.2)octane-2-carboxylic acid
  • Bicyclo(2.2.2)octane-2-carboxylic acid, 3-((5-fluoro-2-(5-fluoro-1H-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)-, (2S,3S)-
  • JNJ-63623872
  • pimodivir
  • VX-787

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
399.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.8
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
399.15068119 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
399.15068119 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
104 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
620
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
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)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Paediatric drug

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Treatment of influenza

6.2 Clinical Trials

6.2.1 ClinicalTrials.gov

6.2.2 EU Clinical Trials Register

6.3 EMA Drug Information

Type
Paediatric investigation
Active Substance
Therapeutic Area
Infectious diseases
Drug Form
Age-appropriate oral solid dosage form
Administration Route
Oral use, Gastric use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2019-01-03

7 Use and Manufacturing

7.1 Uses

7.1.1 Use Classification

Human Drugs -> EU pediatric investigation plans

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

Precautionary Statement Codes

P203, P260, P261, P263, P264, P270, P272, P280, P302+P352, P318, P321, P333+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

8.1.2 Hazard Classes and Categories

Skin Sens. 1B (100%)

Lact. (100%)

9 Associated Disorders and Diseases

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 KEGG : Antimicrobials

14.4 ChemIDplus

14.5 ChEMBL Target Tree

14.6 EPA DSSTox Classification

14.7 PFAS and Fluorinated Organic Compounds in PubChem

14.8 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. ChEMBL
    LICENSE
    Access 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.html
  2. Therapeutic Target Database (TTD)
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless 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
  7. ClinicalTrials.gov
    LICENSE
    The 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
  8. NCI Thesaurus (NCIt)
    LICENSE
    Unless 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-reuse
  9. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  10. EU Clinical Trials Register
  11. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (2S,3S)-3-{[5-FLUORO-2-(5-FLUORO-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)PYRIMIDIN-4-YL]AMINO}BICYCLO[2.2.2]OCTANE-2-CARBOXYLIC ACID (EC: 944-438-9)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/253928
    (2S,3S)-3-{[5-FLUORO-2-(5-FLUORO-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)PYRIMIDIN-4-YL]AMINO}BICYCLO[2.2.2]OCTANE-2-CARBOXYLIC ACID
    https://echa.europa.eu/substance-information/-/substanceinfo/100.245.692
  12. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  13. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  14. Metabolomics Workbench
  15. Protein Data Bank in Europe (PDBe)
  16. Springer Nature
  17. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  18. Wikidata
  19. Wikipedia
  20. PubChem
  21. Medical Subject Headings (MeSH)
    LICENSE
    Works 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.html
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS