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Gallium Maltolate

Gallium Maltolate

Synopsis, Chemistry

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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

Gallium Maltolate

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 Formula	C₁₈H₁₅GaO₉
Molecular Weight	445.0 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	0
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	148
Heavy Atom Count	28
Formal Charge	0
Complexity	200
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	4

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.