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Rabacfosadine

PubChem CID
16047979
Structure
Rabacfosadine_small.png
Molecular Formula
Synonyms
  • Rabacfosadine
  • 859209-74-8
  • GS-9219
  • rabacfosadina
  • GS 9219
Molecular Weight
526.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2007-04-30
  • Modify:
    2025-01-18
Description
Rabacfosadine has been used in trials studying the treatment of Multiple Myeloma, Non-Hodgkin's Lymphoma, and Chronic Lymphocytic Leukemia.
Rabacfosadine is an acyclic nucleotide phosphonate prodrug and polymerase inhibitor that can potentially be used for its antineoplastic activity in the treatment of lymphoma in dogs. Upon administration, rabacfosadine is hydrolyzed intracellularly to 9-(2-phosphonylmethoxyethyl)-N6-cyclopropyl-2, 6-diaminopurine (cPrPMEDAP) and subsequently deaminated to 9-(2-phosphonylmethoxyethyl) guanine (PMEG) and phosphorylated to PMEG diphosphate (PMEGpp). PMEGpp binds to and inhibits DNA polymerases. This inhibits DNA synthesis, resulting in S phase arrest and induction of apoptosis.
RABACFOSADINE is a small molecule drug with a maximum clinical trial phase of II.
See also: Rabacfosadine Succinate (active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Rabacfosadine.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl (2S)-2-[[2-[2-amino-6-(cyclopropylamino)purin-9-yl]ethoxymethyl-[[(2S)-1-ethoxy-1-oxopropan-2-yl]amino]phosphoryl]amino]propanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C21H35N8O6P/c1-5-34-19(30)13(3)27-36(32,28-14(4)20(31)35-6-2)12-33-10-9-29-11-23-16-17(24-15-7-8-15)25-21(22)26-18(16)29/h11,13-15H,5-10,12H2,1-4H3,(H2,27,28,32)(H3,22,24,25,26)/t13-,14-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ANSPEDQTHURSFQ-KBPBESRZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCOC(=O)[C@H](C)NP(=O)(COCCN1C=NC2=C(N=C(N=C21)N)NC3CC3)N[C@@H](C)C(=O)OCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H35N8O6P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 NCI Thesaurus Code

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • diethyl N,N'-(((2-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)ethoxy)methyl)phosphonoyl)di-L-alaninate
  • GS-9219
  • rabacfosadine
  • VDC-1101

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
526.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
17
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
526.24171786 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
526.24171786 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
185 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
760
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
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

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.2.1.1 Animal Drugs
Active Ingredients (Rabacfosadine) -> FDA Greenbook

5 Chemical Vendors

6 Drug and Medication Information

6.1 FDA Green Book

6.2 Clinical Trials

6.2.1 ClinicalTrials.gov

7 Use and Manufacturing

7.1 Uses

7.1.1 Use Classification

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

8 Associated Disorders and Diseases

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

9.5 Chemical-Gene Co-Occurrences in Literature

9.6 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 FDA Green Book Patents

10.4 Chemical Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 NCI Thesaurus Tree

13.3 ChemIDplus

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    N,N′-[[[2-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]ethoxy]methyl]phosphinylidene]bis[L-alanine] 1,1′-ethyl ester
    https://commonchemistry.cas.org/detail?cas_rn=859209-74-8
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  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. Therapeutic Target Database (TTD)
  11. FDA Approved Animal Drug Products (Green Book)
    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
  12. 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
  13. Metabolomics Workbench
  14. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Rabacfosadine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. Springer Nature
  16. Wikidata
  17. Wikipedia
  18. PubChem
  19. 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
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS