Oxamate

Oxamate is the carboxylate anion of oxamic acid.[1] Oxamate has a molecular formula of C2H2NO3− and is an isosteric form of pyruvate. Salts and esters of oxamic acid are known collectively as oxamates.

Oxamate
Names
Other names
Carbamoylformate; amino(oxo)acetate; 2-oxo-2-aminoacetate
Identifiers
3D model (JSmol)
  • C(=O)(C(=O)[O-])N
Properties
C2H2NO3−
Molar mass 88.043 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Oxamate is a competitive inhibitor of the enzyme lactate dehydrogenase.[2] 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.[3]

Oxamate, as a lactate dehydrogenase (LDH) inhibitor, plus phenformin, an anti-diabetic agent, has been tested in conjunction with one another and it was shown that this combination has potential anti-cancer properties.[4] 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 counterbalance the side effects of phenformin.[4]

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.[5]

References
  1. Watts H (1866). A Dictionary of Chemistry. Longman, Green, Roberts & Green. pp. 279–.
  2. Zhai, Xiaoming; Yang, Yang; Wan, Jianmei; Zhu, Ran; Wu, Yiwei (2013-09-19). "Inhibition of LDH-A by oxamate induces G2/M arrest, apoptosis and increases radiosensitivity in nasopharyngeal carcinoma cells". Oncology Reports. 30 (6): 2983–2991. doi:10.3892/or.2013.2735. PMID 24064966.
  3. 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.
  4. 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.
  5. 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. PMC 9134710. PMID 23560609.
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