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    Emvododstat

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    2D Structure
    Also known as: Emvododstat, Ptc299, Ptc-299, 1256565-36-2, Emvododstat [usan], 053qd2i96a
    Molecular Formula
    C25H20Cl2N2O3
    Molecular Weight
    467.3  g/mol
    InChI Key
    SRSHBZRURUNOSM-DEOSSOPVSA-N
    FDA UNII
    053QD2I96A
    Emvododstat is an orally bioavailable, small molecule inhibitor of vascular endothelial growth factor (VEGF) synthesis with potential antiangiogenesis and antineoplastic activities. Emvododstat targets post-transcriptionally by selectively binding the 5'- and 3'-untranslated regions (UTR) of VEGF messenger RNA (mRNA), thereby preventing translation of VEGF. This inhibits VEGF protein production and decreases its levels in the tumor and bloodstream. In turn, this may result in the inhibition of migration, proliferation and survival of endothelial cells, microvessel formation, the inhibition of tumor cell proliferation, and eventually the induction of tumor cell death. VEGFs are upregulated in a variety of tumor cell types and play key roles during angiogenesis. In addition, emvododstat may enhance the antitumor activity of other chemotherapeutic agents.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4-chlorophenyl) (1S)-6-chloro-1-(4-methoxyphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
    2.1.2 InChI
    InChI=1S/C25H20Cl2N2O3/c1-31-18-7-2-15(3-8-18)24-23-20(21-14-17(27)6-11-22(21)28-23)12-13-29(24)25(30)32-19-9-4-16(26)5-10-19/h2-11,14,24,28H,12-13H2,1H3/t24-/m0/s1
    2.1.3 InChI Key
    SRSHBZRURUNOSM-DEOSSOPVSA-N
    2.1.4 Canonical SMILES
    COC1=CC=C(C=C1)C2C3=C(CCN2C(=O)OC4=CC=C(C=C4)Cl)C5=C(N3)C=CC(=C5)Cl
    2.1.5 Isomeric SMILES
    COC1=CC=C(C=C1)[C@H]2C3=C(CCN2C(=O)OC4=CC=C(C=C4)Cl)C5=C(N3)C=CC(=C5)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    053QD2I96A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-chloro-1,3,4,9-tetrahydro-1-(4-methoxyphenyl)-, 4-chlorophenyl Ester, (1s)-2h-pyrido(3,4-b)indole-2-carboxylic Acid

    2. Emvododstat

    3. Ptc299

    2.3.2 Depositor-Supplied Synonyms

    1. Emvododstat

    2. Ptc299

    3. Ptc-299

    4. 1256565-36-2

    5. Emvododstat [usan]

    6. 053qd2i96a

    7. Emvododstat [inn]

    8. Emvododstat [who-dd]

    9. Schembl8509210

    10. Chembl4650336

    11. Gtpl11421

    12. 1219951-09-3

    13. 2h-pyrido(3,4-b)indole-2-carboxylic Acid, 6-chloro-1,3,4,9-tetrahydro-1-(4-methoxyphenyl)-, 4-chlorophenyl Ester, (1s)-

    14. Ex-a5798

    15. At24059

    16. Hy-124593

    17. Cs-0087039

    18. 4-chlorophenyl (1s)-6-chloro-1-(4-methoxyphenyl)-1,3,4,9-tetrahydro-2h-pyrido(3,4-b)indole-2-carboxylate

    19. 4-chlorophenyl (s)-6-chloro-1-(4-methoxyphenyl)-1,3,4,9-tetrahydro-2h-pyrido[3,4-b]indole-2-carboxylate

    2.4 Create Date
    2010-12-13
    3 Chemical and Physical Properties
    Molecular Weight 467.3 g/mol
    Molecular Formula C25H20Cl2N2O3
    XLogP36.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass466.0850979 g/mol
    Monoisotopic Mass466.0850979 g/mol
    Topological Polar Surface Area54.6 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity651
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in cancer/tumors (unspecified) and solid tumors.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    PTC299 demonstrated a broad range of activity in blocking VEGF synthesis in multiple tumor types, including breast, cervical, colorectal, fibrosarcoma, gastric, lung, melanoma, neuroblastoma, ovarian, pancreatic, prostate and renal cell cancer lines. PTC299 as a monotherapy significantly reduced VEGF concentrations in tumors and plasma, reduced tumor blood vessel density, and substantially impeded tumor progression.

    5.2 Mechanism of Action

    PTC299 was designed to inhibit VEGF production in tumors by targeting the post-transcriptional control processes that regulate VEGF formation. Because PTC299 inhibits VEGF production, its action occurs at a different point in the VEGF pathway than therapies, such as Avastin or Sutent. PTC299 may be active both as a single agent or when used in combination with other anti-angiogenic agents or with chemotherapy agents for the treatment of cancers.

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