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    Chemistry

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    Also known as: Vazegepant, Bms-742413, Bhv-3500, Zavegepant [usan], Odu3zaz94j, Bms-742413-01
    Molecular Formula
    C36H46N8O3
    Molecular Weight
    638.8  g/mol
    InChI Key
    JJVAPHYEOZSKJZ-JGCGQSQUSA-N
    FDA UNII
    ODU3ZAZ94J
    Zavegepant HCl
    Zavegepant is a highly soluble small molecule calcitonin gene related peptide (CGRP) receptor antagonist, with potential analgesic and immunomodulating activities. Upon administration, zavegepant targets, binds to and inhibits the activity of CGRP receptors located on mast cells in the brain. This may inhibit neurogenic inflammation caused by trigeminal nerve release of CGRP. In addition, by blocking the CGRP receptors located in smooth muscle cells within vessel walls, zavegepant inhibits the pathologic dilation of intracranial arteries. Zavegepant, by blocking the CGRP receptors, also suppresses the transmission of pain by inhibiting the central relay of pain signals from the trigeminal nerve to the caudal trigeminal nucleus. Altogether, this may relieve migraine. As CGRP receptors induce the release of pro-inflammatory mediators, such as interleukin-6 (IL-6), from inflammatory cells, zavegepant may prevent an IL-6-mediated inflammatory response. Zavegepant may also inhibit the CGRP-mediated induction of eosinophil migration and the stimulation of beta-integrin-mediated T cell adhesion to fibronectin at the site of inflammation, and may abrogate the CGRP-mediated polarization of the T cell response towards the pro-inflammatory state characterized by Th17 and IL-17. This may improve lung inflammation and oxygenation, prevent edema, and further lung injury. CGRP, a 37 amino-acid peptide expressed in and released from a subset of polymodal primary sensory neurons of the trigeminal ganglion and nerve fibers projecting to the airways and by pulmonary neuroendocrine cells, plays an important role in pain transmission, inflammation, and neurogenic vasodilatation. It is released upon acute lung injury and upregulation of transient receptor potential (TRP) channels.
    1 2D Structure

    Zavegepant HCl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(2R)-3-(7-methyl-1H-indazol-5-yl)-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxopropan-2-yl]-4-(2-oxo-1H-quinolin-3-yl)piperidine-1-carboxamide
    2.1.2 InChI
    InChI=1S/C36H46N8O3/c1-24-19-25(20-28-23-37-40-33(24)28)21-32(35(46)43-17-15-42(16-18-43)29-9-11-41(2)12-10-29)39-36(47)44-13-7-26(8-14-44)30-22-27-5-3-4-6-31(27)38-34(30)45/h3-6,19-20,22-23,26,29,32H,7-18,21H2,1-2H3,(H,37,40)(H,38,45)(H,39,47)/t32-/m1/s1
    2.1.3 InChI Key
    JJVAPHYEOZSKJZ-JGCGQSQUSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=CC2=C1NN=C2)CC(C(=O)N3CCN(CC3)C4CCN(CC4)C)NC(=O)N5CCC(CC5)C6=CC7=CC=CC=C7NC6=O
    2.1.5 Isomeric SMILES
    CC1=CC(=CC2=C1NN=C2)C[C@H](C(=O)N3CCN(CC3)C4CCN(CC4)C)NC(=O)N5CCC(CC5)C6=CC7=CC=CC=C7NC6=O
    2.2 Other Identifiers
    2.2.1 UNII
    ODU3ZAZ94J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bms 742413

    2. Bms-742413

    3. N-(3-(7-methyl-1h-indazol-5-yl)-1-(4-(1-methylpiperidin-4-yl)-1-oxopropan-2-yl))-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide

    2.3.2 Depositor-Supplied Synonyms

    1. Vazegepant

    2. Bms-742413

    3. Bhv-3500

    4. Zavegepant [usan]

    5. Odu3zaz94j

    6. Bms-742413-01

    7. 1337918-83-8

    8. Chembl2397415

    9. N-[(2r)-3-(7-methyl-1h-indazol-5-yl)-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxopropan-2-yl]-4-(2-oxo-1h-quinolin-3-yl)piperidine-1-carboxamide

    10. 1-piperidinecarboxamide, 4-(1,2-dihydro-2-oxo-3-quinolinyl)-n-((1r)-1-((7-methyl-1h-indazol-5-yl)methyl)-2-(4-(1-methyl-4-piperidinyl)-1-piperazinyl)-2-oxoethyl)-

    11. 4-(1,2-dihydro-2-oxo-3-quinolinyl)-n-((1r)-1-((7-methyl-1h-indazol-5-yl)methyl)-2-(4-(1-methyl-4-piperidinyl)-1-piperazinyl)-2-oxoethyl)-1-piperidinecarboxamide

    12. Zavegepant [inn]

    13. Unii-odu3zaz94j

    14. Vazegepant [who-dd]

    15. Schembl107428

    16. Gtpl11513

    17. Ex-a6698

    18. Bdbm50436107

    19. Bms742413

    20. Who 11512

    21. Hy-134992

    22. Cs-0168642

    2.4 Create Date
    2011-11-07
    3 Chemical and Physical Properties
    Molecular Weight 638.8 g/mol
    Molecular Formula C36H46N8O3
    XLogP33.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass638.36928736 g/mol
    Monoisotopic Mass638.36928736 g/mol
    Topological Polar Surface Area117 Ų
    Heavy Atom Count47
    Formal Charge0
    Complexity1160
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

    API Reference Price

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