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    Gallium Maltolate

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 108560-70-9, Gallium tris(2-methyl-4-oxo-4h-pyran-3-olate), 17lei49c2g, Gallium maltolate [inci], Gallium;2-methyl-4-oxopyran-3-olate, Db05420
    Molecular Formula
    C18H15GaO9
    Molecular Weight
    445.0  g/mol
    InChI Key
    ASYYOZSDALANRF-UHFFFAOYSA-K
    FDA UNII
    17LEI49C2G
    Gallium Maltolate is an orally bioavailable form of the element gallium (Ga) composed of a trivalent gallium cation (Ga3+) coordinated to three maltolate ligands, with anti-inflammatory, anti-proliferative, antineoplastic, analgesic, antiresorptive and antibacterial activities. Upon administration of gallium maltolate, Ga3+, which is structurally similar to the ferric ion (Fe3+), competes with and replaces Fe3+ in many vital Fe 3+-mediated biological reactions.. Unlike Fe3+, Ga3+ cannot be reduced, cannot participate in redox reactions and cannot mimic Fe3+ functions. In rapidly proliferating cells, such as cancer cells, high amounts of iron are needed for DNA synthesis. The incorporation of Ga3+ inactivates the Fe3+-dependent enzyme ribonucleotide reductase (RR), an enzyme essential for DNA synthesis, leading to an inhibition of DNA synthesis and induction of cell death in rapidly proliferating cells. Gallium similarly reduces bacterial cell growth. In addition, Ga3+ is able to suppress inflammation through the down-regulation of pro-inflammatory cells and the inhibition of pro-inflammatory cytokine secretion. Gallium also exerts analgesic effects due to the inhibition of Fe3+-dependent enzymes involved in inflammation and may interfere with the activity of certain metalloproteinases and neuropeptides that are implicated in pain. Also, gallium is able to inhibit bone resorption by osteoclasts, may inhibit metastasis to bone and may prevent the destruction of bone by tumors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    gallium;2-methyl-4-oxopyran-3-olate
    2.1.2 InChI
    InChI=1S/3C6H6O3.Ga/c3*1-4-6(8)5(7)2-3-9-4;/h3*2-3,8H,1H3;/q;;;+3/p-3
    2.1.3 InChI Key
    ASYYOZSDALANRF-UHFFFAOYSA-K
    2.1.4 Canonical SMILES
    CC1=C(C(=O)C=CO1)[O-].CC1=C(C(=O)C=CO1)[O-].CC1=C(C(=O)C=CO1)[O-].[Ga+3]
    2.2 Other Identifiers
    2.2.1 UNII
    17LEI49C2G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4h-pyran-4-one, 3-hydroxy-2-methyl-, Gallium Salt (3:1)

    2. Tris(3-hydroxy-2-methyl-4h-pyran-4-onato)gallium(iii)

    3. Tris(maltolato)gallium(iii)

    2.3.2 Depositor-Supplied Synonyms

    1. 108560-70-9

    2. Gallium Tris(2-methyl-4-oxo-4h-pyran-3-olate)

    3. 17lei49c2g

    4. Gallium Maltolate [inci]

    5. Gallium;2-methyl-4-oxopyran-3-olate

    6. Db05420

    7. B2699-054157

    8. 3-bis[(2-methyl-4-oxopyran-3-yl)oxy]gallanyloxy-2-methylpyran-4-one

    9. Gallium, Tris(3-(hydroxy-.kappa.o)-2-methyl-4h-pyran-4-onato-.kappa.o4)-, (oc-6-21)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 445.0 g/mol
    Molecular Formula C18H15GaO9
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count0
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area148
    Heavy Atom Count28
    Formal Charge0
    Complexity200
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Investigated for use/treatment in bladder cancer, lymphoma (unspecified), multiple myeloma, paget's disease, and prostate cancer.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    Gallium maltolate is a novel orally active formulation of gallium, a semi-metallic element that is a potent inhibitor of ribonucleotide reductase, an enzyme that promotes tumor growth.Gallium is also known to concentrate in malignant tumors and sites of infection, and appears to favorably impact calcium deposition, making bones more resistant to degradation caused by cancer metastasis. Titan's novel product, gallium maltolate, may significantly expand the therapeutic potential of gallium by providing the advantages of enhanced bioavailablity, a potentially improved therapeutic profile and ease of administration.