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    Chemistry

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    Also known as: 1239908-20-3, Ixazomib citrate (ester), Ixazomib citrate [usan], 46cwk97z3k, 2-[4-(carboxymethyl)-2-[(1r)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-5-oxo-1,3,2-dioxaborolan-4-yl]acetic acid, Unii-46cwk97z3k
    Molecular Formula
    C20H23BCl2N2O9
    Molecular Weight
    517.1  g/mol
    InChI Key
    MBOMYENWWXQSNW-AWEZNQCLSA-N
    FDA UNII
    46CWK97Z3K
    Ixazomib Citrate
    Ixazomib Citrate is the citrate salt form of ixazomib, an orally bioavailable second generation proteasome inhibitor (PI) with potential antineoplastic activity. Ixazomib inhibits the activity of the proteasome, blocking the targeted proteolysis normally performed by the proteasome, which results in an accumulation of unwanted or misfolded proteins; disruption of various cell signaling pathways may follow, resulting in the induction of apoptosis. Compared to first generation PIs, second generation PIs may have an improved pharmacokinetic profile with increased potency and less toxicity. Proteasomes are large protease complexes that degrade unneeded or damaged proteins that have been ubiquinated.
    1 2D Structure

    Ixazomib Citrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-(carboxymethyl)-2-[(1R)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-5-oxo-1,3,2-dioxaborolan-4-yl]acetic acid
    2.1.2 InChI
    InChI=1S/C20H23BCl2N2O9/c1-10(2)5-14(21-33-19(32)20(34-21,7-16(27)28)8-17(29)30)25-15(26)9-24-18(31)12-6-11(22)3-4-13(12)23/h3-4,6,10,14H,5,7-9H2,1-2H3,(H,24,31)(H,25,26)(H,27,28)(H,29,30)/t14-/m0/s1
    2.1.3 InChI Key
    MBOMYENWWXQSNW-AWEZNQCLSA-N
    2.1.4 Canonical SMILES
    B1(OC(=O)C(O1)(CC(=O)O)CC(=O)O)C(CC(C)C)NC(=O)CNC(=O)C2=C(C=CC(=C2)Cl)Cl
    2.1.5 Isomeric SMILES
    B1(OC(=O)C(O1)(CC(=O)O)CC(=O)O)[C@H](CC(C)C)NC(=O)CNC(=O)C2=C(C=CC(=C2)Cl)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    46CWK97Z3K
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1239908-20-3

    2. Ixazomib Citrate (ester)

    3. Ixazomib Citrate [usan]

    4. 46cwk97z3k

    5. 2-[4-(carboxymethyl)-2-[(1r)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-5-oxo-1,3,2-dioxaborolan-4-yl]acetic Acid

    6. Unii-46cwk97z3k

    7. 1,3,2-dioxaborolane-4,4-diacetic Acid, 2-((1r)-1-((2-((2,5-dichlorobenzoyl)amino)acetyl)amino)-3-methylbutyl)-5-oxo-

    8. 1,3,2-dioxaborolane-4,4-diacetic Acid, 2-[(1r)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-5-oxo-

    9. 2,2'-(2-((1r)-1-((n-(2,5-dichlorobenzoyl)glycyl)amino)-3-methylbutyl)-5-oxo-1,3,2-dioxaborolane-4,4-diyl)diacetic Acid

    10. 2,2'-{2-[(1r)-1-{[n-(2,5-dichlorobenzoyl)glycyl]amino}-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diyl}diacetic Acid

    11. Ninlaro (tn)

    12. Ixazomib Citrate [mi]

    13. Ixazomib Citrate (jan/usan)

    14. Ixazomib Citrate [jan]

    15. Schembl4427479

    16. Chembl3545432

    17. Chebi:90939

    18. Dtxsid60924652

    19. Ixazomib Citrate [who-dd]

    20. Bcp16600

    21. Ex-a3660

    22. Nsc767907

    23. S4432

    24. Akos030632768

    25. Ixazomib Citrate [orange Book]

    26. Zinc200299610

    27. Cs-1720

    28. Nsc-767907

    29. Ncgc00522453-01

    30. Ncgc00522453-02

    31. 2,2'-{2-[(1r)-1-({[(2,5-dichlorobenzoyl)amino]acetyl}amino)-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diyl}diacetic Acid

    32. Ac-35344

    33. As-75031

    34. Hy-10452

    35. C71946

    36. D10131

    37. Mln9708; Mln-9708; Mln 9708;ixazomib-prodrug

    38. Q27162929

    39. (r)-2,2'-(2-(1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-5-oxo-1,3,2-dioxaborolane-4,4-diyl)diacetic Acid

    40. 2,2'-{2-[(1r)-1-({[(2,5-dichlorobenzoy)amino]acetyl}amino)-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diyl}diacetic Acid

    41. 2-[(1r)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diacetic Acid

    42. 2-[4-(carboxymethyl)-2-[(1r)-1-{2-[(2,5-dichlorophenyl)formamido]acetamido}-3-methylbutyl]-5-oxo-1,3,2-dioxaborolan-4-yl]acetic Acid

    2.3.2 Other Synonyms

    1. Ixazomib

    2.4 Create Date
    2012-03-21
    3 Chemical and Physical Properties
    Molecular Weight 517.1 g/mol
    Molecular Formula C20H23BCl2N2O9
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count11
    Exact Mass516.0873659 g/mol
    Monoisotopic Mass516.0873659 g/mol
    Topological Polar Surface Area168 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity797
    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

    Treatment of systemic light chain amyloidosis

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    28-Aug-2023
    31-Jul-2024
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