Oxamate

Oxamate is a salt of oxamic acid.[1] Oxamate has a molecular formula of C₂H₂NO₃⁻ an isosteric form of pyruvate. Oxamate is a noncompetitive inhibitor of the enzyme lactate dehydrogenase. Oxamate is a possible pyruvate analog that has the ability to halt lactate production by inhibiting lactate dehydrogenase, effectively stopping the conversation process of pyruvate to lactate.[2]

Oxamate [lactate dehydrogenase (LDH) inhibitor] plus Phenformin (phenethylbiguanide; an anti-diabetic agent) has been tested in conjunction with one another and it was shown that this combination has potential anti-cancer properties.[3] Phenformin when administered by itself has a high incidence of lactic acidosis. Due to the inherent ability of Oxamate to prevent the conversion of pyruvate to lactate, oxamate can be used to counter balance the side effects of Phenformin.[3]

Oxamate also plays inhibiting roles with Oxaloacetate, an important intermediate for the Citric acid cycle. Oxamate competes and binds to the Carboxyl transferase domain active site, and reverses the reaction of oxalaoacetate decarboxylation by Pyruvate carboxylase.[4]

References

Watts H (1866). A Dictionary of Chemistry. Longman, Green, Roberts & Green. pp. 279–.
Ye W, Zheng Y, Zhang S, Yan L, Cheng H, Wu M (2016-03-03). "Oxamate Improves Glycemic Control and Insulin Sensitivity via Inhibition of Tissue Lactate Production in db/db Mice". PLOS One. 11 (3): e0150303. doi:10.1371/journal.pone.0150303. PMC 4777529. PMID 26938239.
Miskimins WK, Ahn HJ, Kim JY, Ryu S, Jung YS, Choi JY (2014). "Synergistic anti-cancer effect of phenformin and oxamate". PLOS One. 9 (1): e85576. doi:10.1371/journal.pone.0085576. PMC 3897486. PMID 24465604.
Marlier JF, Cleland WW, Zeczycki TN (April 2013). "Oxamate is an alternative substrate for pyruvate carboxylase from Rhizobium etli". Biochemistry. 52 (17): 2888–94. doi:10.1021/bi400075t. PMID 23560609.

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[Watts1866-1] Watts H (1866). A Dictionary of Chemistry. Longman, Green, Roberts & Green. pp. 279–.

[2] Ye W, Zheng Y, Zhang S, Yan L, Cheng H, Wu M (2016-03-03). "Oxamate Improves Glycemic Control and Insulin Sensitivity via Inhibition of Tissue Lactate Production in db/db Mice". PLOS One. 11 (3): e0150303. doi:10.1371/journal.pone.0150303. PMC 4777529. PMID 26938239.

[Miskimins_2014-3] Miskimins WK, Ahn HJ, Kim JY, Ryu S, Jung YS, Choi JY (2014). "Synergistic anti-cancer effect of phenformin and oxamate". PLOS One. 9 (1): e85576. doi:10.1371/journal.pone.0085576. PMC 3897486. PMID 24465604.

[4] Marlier JF, Cleland WW, Zeczycki TN (April 2013). "Oxamate is an alternative substrate for pyruvate carboxylase from Rhizobium etli". Biochemistry. 52 (17): 2888–94. doi:10.1021/bi400075t. PMID 23560609.