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    Endostatin

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: N-methyl-n-phenacylnitrous amide, 55984-52-6, 187888-07-9, Ethanone, 2-(methylnitrosoamino)-1-phenyl-, 2-oxo-2-phenylethylmethylnitrosamine, Dtxsid10204557
    Molecular Formula
    C9H10N2O2
    Molecular Weight
    178.19  g/mol
    InChI Key
    AAFYOVPTFNNVDN-UHFFFAOYSA-N
    Angiostatic proteins that are formed from proteolytic cleavage of COLLAGEN TYPE XVIII.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-methyl-N-phenacylnitrous amide
    2.1.2 InChI
    InChI=1S/C9H10N2O2/c1-11(10-13)7-9(12)8-5-3-2-4-6-8/h2-6H,7H2,1H3
    2.1.3 InChI Key
    AAFYOVPTFNNVDN-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(CC(=O)C1=CC=CC=C1)N=O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Endostatins

    2.2.2 Depositor-Supplied Synonyms

    1. N-methyl-n-phenacylnitrous Amide

    2. 55984-52-6

    3. 187888-07-9

    4. Ethanone, 2-(methylnitrosoamino)-1-phenyl-

    5. 2-oxo-2-phenylethylmethylnitrosamine

    6. Dtxsid10204557

    7. Zinc5965474

    2.3 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 178.19 g/mol
    Molecular Formula C9H10N2O2
    XLogP31.6
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass178.074227566 g/mol
    Monoisotopic Mass178.074227566 g/mol
    Topological Polar Surface Area49.7 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity188
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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), macular degeneration, and diabetic retinopathy.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Angiogenesis Inhibitors

    Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.2 Mechanism of Action

    Endostatin is an endogenous antitumor protein. Endostatin is a 20-kDa C-terminal fragment derived from type XVIII collagen which inhibits cell proliferation and migration, and induces endothelial cell apoptosis and cell cycle arrest. It is proposed that endostatin's effects are due to inhibition of vascular endothelial growth factor (VEGF) tyrosine phosphorylation of KDR/F1k-1 (VEGF receptor 2), the cell surface receptor for VEGF. VEGF is an important mediator of angiogensis. Endostatin additionally blocks activation of extracellular signal related kinases, or ERK, protein 38 mitogen activated protein kinase, or p38 MAPK (signal transduction pathways involving kinases that couple growth factors to cell surface receptors), as well as focal adhesion kinase (p125FAK). Studies are being done to determine if endostatin has possible impact on other pathways, and may also target E-selectin and block activity of metalloproteinases 2, 9 and 13. There is further research into a possible mechanistic link involving endostatin's angiogenic and zinc binding ability.