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    Glatiramer

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    PharmaCompass
    $ API Ref.Price (USD/KG) : 176,983Xls

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    2D Structure
    Also known as: 28704-27-0, Cop-1, (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid, Dtxsid50182865
    Molecular Formula
    C23H41N5O11
    Molecular Weight
    563.6  g/mol
    InChI Key
    YLOCGHYTXIINAI-XKUOMLDTSA-N
    Glatiramer acetate consists of the acetate salts of synthetic polypeptides, containing four naturally occurring amino acids: L-glutamic acid, L-alanine, L-tyrosine, and L-lysine with an average molar fraction of 0.141, 0.427, 0.095, and 0.338, respectively. The average molecular weight of glatiramer acetate is 5,000-9,000 daltons. It is an immunomodulator, licensed in much of the world for reduced frequency of relapses in relapsing-remitting multiple sclerosis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-aminopentanedioic acid;(2S)-2-aminopropanoic acid;(2S)-2,6-diaminohexanoic acid
    2.1.2 InChI
    InChI=1S/C9H11NO3.C6H14N2O2.C5H9NO4.C3H7NO2/c10-8(9(12)13)5-6-1-3-7(11)4-2-6;7-4-2-1-3-5(8)6(9)10;6-3(5(9)10)1-2-4(7)8;1-2(4)3(5)6/h1-4,8,11H,5,10H2,(H,12,13);5H,1-4,7-8H2,(H,9,10);3H,1-2,6H2,(H,7,8)(H,9,10);2H,4H2,1H3,(H,5,6)/t8-;5-;3-;2-/m0000/s1
    2.1.3 InChI Key
    YLOCGHYTXIINAI-XKUOMLDTSA-N
    2.1.4 Canonical SMILES
    CC(C(=O)O)N.C1=CC(=CC=C1CC(C(=O)O)N)O.C(CCN)CC(C(=O)O)N.C(CC(=O)O)C(C(=O)O)N
    2.1.5 Isomeric SMILES
    C[C@@H](C(=O)O)N.C1=CC(=CC=C1C[C@@H](C(=O)O)N)O.C(CCN)C[C@@H](C(=O)O)N.C(CC(=O)O)[C@@H](C(=O)O)N
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. 28704-27-0

    2. Cop-1

    3. (2s)-2-amino-3-(4-hydroxyphenyl)propanoic Acid;(2s)-2-aminopentanedioic Acid;(2s)-2-aminopropanoic Acid;(2s)-2,6-diaminohexanoic Acid

    4. Dtxsid50182865

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 563.6 g/mol
    Molecular Formula C23H41N5O11
    Hydrogen Bond Donor Count11
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count13
    Exact Mass563.28025714 g/mol
    Monoisotopic Mass563.28025714 g/mol
    Topological Polar Surface Area337 Ų
    Heavy Atom Count39
    Formal Charge0
    Complexity488
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count4
    4 Drug and Medication Information
    4.1 Drug Indication

    For reduction of the frequency of relapses in patients with Relapsing-Remitting Multiple Sclerosis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Glatiramer acetate was originally designed to mimic a protein in myelin, called myelin basic protein, with the intention of inducing EAE (an animal model of MS). Quite to the contrary, it was found to suppress the disease and as a result came to be trialed in human MS. There is some evidence that Glatiramer acetate converts the body's immune response from a Th1 type to a Th2 one, promotes suppressor T cells or acts as an altered peptide ligand. Studies in animals and in vitro systems suggest that upon its administration, glatiramer acetate-specific suppressor T-cells are induced and activated in the periphery. Some fraction of the injected material, either intact or partially hydrolyzed, is presumed to enter the lymphatic circulation, enabling it to reach regional lymph nodes, and some may enter the systemic circulation intact.

    5.2 Metabolism/Metabolites

    Hydrolyzed by proteases

    5.3 Mechanism of Action

    Glatiramer acetate (GA) exhibits strong and promiscuous binding to MHC molecules (HLA DRB1* variants) and consequent competition with various myelin antigens for their presentation to T cells. A further aspect of its action is potent induction of specific suppressor cells of the T helper 2 (Th2) type that migrate to the brain and lead to in situ bystander suppression. Furthermore, the GA-specific cells in the brain express the anti-inflammatory cytokines IL-10 and transforming growth factor beta, in addition to brain-derived neurotrophic factor, whereas they do not express the inflammatory cytokine IFN-gamma. Recent evidence also suggests that Glatiramer acetate directly inhibits dendritic cells and monocytes - both of which are circulating antigen presenting cells.