Gallium maltolate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529419

CAS#: 108560-70-9

Description: Gallium maltolate is a ribonucleoside-diphosphate reductase inhibitor potentially for the treatment of prostate cancer


Price and Availability

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Gallium maltolate, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529419
Name: Gallium maltolate
CAS#: 108560-70-9
Chemical Formula: C18H15GaO9
Exact Mass: 443.9972
Molecular Weight: 445.03
Elemental Analysis: C, 48.58; H, 3.40; Ga, 15.67; O, 32.36


Synonym:

IUPAC/Chemical Name: gallium tris(2-methyl-4-oxo-4H-pyran-3-olate)

InChi Key: ASYYOZSDALANRF-UHFFFAOYSA-K

InChi Code: InChI=1S/3C6H6O3.Ga/c3*1-4-6(8)5(7)2-3-9-4;/h3*2-3,8H,1H3;/q;;;+3/p-3

SMILES Code: [O-]C1=C(C)OC=CC1=O.[O-]C2=C(C)OC=CC2=O.[O-]C3=C(C)OC=CC3=O.[Ga+3]


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Ball KR, Sampieri F, Chirino M, Hamilton DL, Blyth RI, Sham TK, Dowling PM, Thompson J. Synchrotron X-ray fluorescence microscopy of gallium in bladder tissue following gallium maltolate administration during urinary tract infection. Antimicrob Agents Chemother. 2013 Nov;57(11):5197-201. doi: 10.1128/AAC.00616-13. PubMed PMID: 23877680; PubMed Central PMCID: PMC3811287.

2: Cohen ND, Slovis NM, Giguère S, Baker S, Chaffin MK, Bernstein LR. Gallium maltolate as an alternative to macrolides for treatment of presumed Rhodococcus equi pneumonia in foals. J Vet Intern Med. 2015 May-Jun;29(3):932-9. doi: 10.1111/jvim.12595. PubMed PMID: 25868480; PubMed Central PMCID: PMC4895420.

3: Chaffin MK, Cohen ND, Martens RJ, O'Conor M, Bernstein LR. Evaluation of the efficacy of gallium maltolate for chemoprophylaxis against pneumonia caused by Rhodococcus equi infection in foals. Am J Vet Res. 2011 Jul;72(7):945-57. doi: 10.2460/ajvr.72.7.945. PubMed PMID: 21728856.

4: Chitambar CR, Purpi DP, Woodliff J, Yang M, Wereley JP. Development of gallium compounds for treatment of lymphoma: gallium maltolate, a novel hydroxypyrone gallium compound, induces apoptosis and circumvents lymphoma cell resistance to gallium nitrate. J Pharmacol Exp Ther. 2007 Sep;322(3):1228-36. PubMed PMID: 17600139.

5: Monk CS, Sweeney RW, Bernstein LR, Fecteau ME. Serum and tissue concentrations of gallium after oral administration of gallium nitrate and gallium maltolate to neonatal calves. Am J Vet Res. 2016 Feb;77(2):151-5. doi: 10.2460/ajvr.77.2.151. PubMed PMID: 27027708.

6: Wu X, Wang TW, Lessmann GM, Saleh J, Liu X, Chitambar CR, Hwang ST. Gallium maltolate inhibits human cutaneous T-cell lymphoma tumor development in mice. J Invest Dermatol. 2015 Mar;135(3):877-84. doi: 10.1038/jid.2014.476. PubMed PMID: 25371972.

7: Sampieri F, Alcorn J, Allen AL, Clark CR, Vannucci FA, Pusterla N, Mapes S, Ball KR, Dowling PM, Thompson J, Bernstein LR, Gebhart CJ, Hamilton DL. Pharmacokinetics of gallium maltolate in Lawsonia intracellularis-infected and uninfected rabbits. J Vet Pharmacol Ther. 2014 Oct;37(5):486-99. doi: 10.1111/jvp.12114. PubMed PMID: 24628462.

8: Fecteau ME, Aceto HW, Bernstein LR, Sweeney RW. Comparison of the antimicrobial activities of gallium nitrate and gallium maltolate against Mycobacterium avium subsp. paratuberculosis in vitro. Vet J. 2014 Oct;202(1):195-7. doi: 10.1016/j.tvjl.2014.06.023. PubMed PMID: 25155307.

9: Bernstein LR. Successful treatment of refractory postherpetic neuralgia with topical gallium maltolate: case report. Pain Med. 2012 Jul;13(7):915-8. doi: 10.1111/j.1526-4637.2012.01404.x. PubMed PMID: 22680305.

10: Norman TE, Batista M, Lawhon SD, Zhang S, Kuskie KR, Swinford AK, Bernstein LR, Cohen ND. In vitro susceptibility of equine-obtained isolates of Corynebacterium pseudotuberculosis to gallium maltolate and 20 other antimicrobial agents. J Clin Microbiol. 2014 Jul;52(7):2684-5. doi: 10.1128/JCM.01252-14. PubMed PMID: 24829243; PubMed Central PMCID: PMC4097677.

11: Arnold CE, Bordin A, Lawhon SD, Libal MC, Bernstein LR, Cohen ND. Antimicrobial activity of gallium maltolate against Staphylococcus aureus and methicillin-resistant S. aureus and Staphylococcus pseudintermedius: An in vitro study. Vet Microbiol. 2012 Mar 23;155(2-4):389-94. doi: 10.1016/j.vetmic.2011.09.009. PubMed PMID: 21963417.

12: Pollina GF, Pepe M, Dean A, Di Marco V, Marton D. Reduction in absorption of gallium maltolate in adult horses following oral administration with food: chemistry and pharmacokinetics. J Vet Pharmacol Ther. 2013 Oct;36(5):456-61. PubMed PMID: 23980593.

13: Bernstein LR, van der Hoeven JJ, Boer RO. Hepatocellular carcinoma detection by gallium scan and subsequent treatment by gallium maltolate: rationale and case study. Anticancer Agents Med Chem. 2011 Jul;11(6):585-90. PubMed PMID: 21554205.

14: Sampieri F, Allen AL, Alcorn J, Clark CR, Vannucci FA, Pusterla N, Mapes SM, Ball KR, Dowling PM, Thompson J, Bernstein LR, Gebhart CJ, Hamilton DL. Efficacy of gallium maltolate against Lawsonia intracellularis infection in a rabbit model. J Vet Pharmacol Ther. 2014 Dec;37(6):571-8. doi: 10.1111/jvp.12132. PubMed PMID: 24730377.

15: Nerren JR, Edrington TS, Bernstein LR, Farrow RL, Genovese KG, Callaway TR, Anderson RC, Krueger NA, Duke SE, Nisbet DJ. Evaluation of the effect of gallium maltolate on fecal Salmonella shedding in cattle. J Food Prot. 2011 Apr;74(4):524-30. doi: 10.4315/0362-028X.JFP-10-298. PubMed PMID: 21477464.

16: Chua MS, Bernstein LR, Li R, So SK. Gallium maltolate is a promising chemotherapeutic agent for the treatment of hepatocellular carcinoma. Anticancer Res. 2006 May-Jun;26(3A):1739-43. PubMed PMID: 16827101.

17: Coleman M, Kuskie K, Liu M, Chaffin K, Libal M, Giguère S, Bernstein L, Cohen N. In vitro antimicrobial activity of gallium maltolate against virulent Rhodococcus equi. Vet Microbiol. 2010 Nov 20;146(1-2):175-8. doi: 10.1016/j.vetmic.2010.05.027. PubMed PMID: 20554401.

18: Arnold C, Chaffin MK, Cohen N, Fajt VR, Taylor RJ, Bernstein LR. Pharmacokinetics of gallium maltolate after intragastric administration in adult horses. Am J Vet Res. 2010 Nov;71(11):1371-6. doi: 10.2460/ajvr.71.11.1371. PubMed PMID: 21034329.

19: Chaffin MK, Fajt V, Martens RJ, Arnold CE, Cohen ND, O'Conor M, Taylor RJ, Bernstein LR. Pharmacokinetics of an orally administered methylcellulose formulation of gallium maltolate in neonatal foals. J Vet Pharmacol Ther. 2010 Aug;33(4):376-82. doi: 10.1111/j.1365-2885.2009.01150.x. PubMed PMID: 20646200.

20: Coleman M, Kuskie K, Liu M, Chaffin K, Libal M, Giguère S, Bernstein L, Cohen N. Corrigendum to: "In vitro antimicrobial activity of gallium maltolate against virulent Rhodococcus equi " [Veterinary Microbiology 146 (2010) 175-178]. Vet Microbiol. 2016 Nov 15;195:165. doi: 10.1016/j.vetmic.2016.09.004. PubMed PMID: 27771063.