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    Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-8a-(2-propenyl)-, (8aR)-

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    2D Structure
    Also known as: Nnz-2591, 2t1hu6069s, Nnz 2591, 847952-38-9, Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-8a-2-propen-1-yl-, (8ar)-, Unii-2t1hu6069s
    Molecular Formula
    C10H14N2O2
    Molecular Weight
    194.23  g/mol
    InChI Key
    WVKCGUOWPZAROG-JTQLQIEISA-N
    FDA UNII
    2T1HU6069S
    NNZ-2591 (cyclo-L-glycyl-L-2-allylproline) is an investigational synthetic analog of cyclic glycine-proline (cGP), a breakdown product of human insulin-like growth factor 1 (IGF-1), that has been chemically modified to increase its half-life, stability, and oral bioavailability. It is currently under development by Neuren Pharmaceuticals for the symptomatic treatment of Angelman, Phelan-McDermid, and Pitt Hopkins Syndromes. It was granted Orphan Drug Designation by the FDA in October 2019 and was granted a patent by the European Patent Office in December 2019. Clinical trials are expected to begin in 2020.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8aR)-8a-prop-2-enyl-3,6,7,8-tetrahydro-2H-pyrrolo[1,2-a]pyrazine-1,4-dione
    2.1.2 InChI
    InChI=1S/C10H14N2O2/c1-2-4-10-5-3-6-12(10)8(13)7-11-9(10)14/h2H,1,3-7H2,(H,11,14)/t10-/m0/s1
    2.1.3 InChI Key
    WVKCGUOWPZAROG-JTQLQIEISA-N
    2.1.4 Canonical SMILES
    C=CCC12CCCN1C(=O)CNC2=O
    2.1.5 Isomeric SMILES
    C=CC[C@@]12CCCN1C(=O)CNC2=O
    2.2 Other Identifiers
    2.2.1 UNII
    2T1HU6069S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cyclo-l-glycyl-l-2-allylproline

    2. Nnz-2591

    2.3.2 Depositor-Supplied Synonyms

    1. Nnz-2591

    2. 2t1hu6069s

    3. Nnz 2591

    4. 847952-38-9

    5. Pyrrolo(1,2-a)pyrazine-1,4-dione, Hexahydro-8a-2-propen-1-yl-, (8ar)-

    6. Unii-2t1hu6069s

    7. Schembl8235982

    8. Chembl4802144

    9. Db15601

    10. Sb18938

    11. Cyclo(-l-glycyl-l-2-allylproline)

    12. Hy-148195

    13. Cs-0615785

    14. Q27255561

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 194.23 g/mol
    Molecular Formula C10H14N2O2
    XLogP30.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass194.105527694 g/mol
    Monoisotopic Mass194.105527694 g/mol
    Topological Polar Surface Area49.4 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity301
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Mechanism of Action

    Insulin-like growth factor 1 (IGF-1) is a hormone secreted by glia and neurons of the CNS that plays an important role in normal brain development and response to pathologies. It is broken down into two separate molecules in the brain, both of which have synthetic analogues in development. [Glypromate], or GPE, comprises the last three peptides of IGF-1 and acts on glial cells, in contrast to its parent compound which tends to act on neurons - a synthetic analogue, [trofinetide], is currently under development by Neuren Pharmaceuticals for the treatment of traumatic brain injury, Rett Syndrome, and Fragile X Syndrome. Glypromate is further cleaved into cyclic glycine-proline (cGP), which serves a number of diverse roles including the regulation of IGF-1 bioavailability, and of which NNZ-2591 is a synthetic analogue. While the specific actions of NNZ-2591 will likely become clearer following clinical trials, IGF-1 and its derivatives are known to facilitate brain development and normal functioning by regulating responses to disease, stress, injury through a number of signaling pathways. For this reason, any therapeutic benefit observed with NNZ-2591 is likely to be the result of many diverse effects rather than action on a specific target.