Oxamate is the
carboxylate anion of
oxamic acid.
Oxamate has a molecular formula of C
2H
2NO
3− and is an
isosteric Classical Isosteres are molecules or ions with similar shape and often electronic properties. Many definitions are available. but the term is usually employed in the context of bioactivity and drug development. Such biologically-active compounds c ...
form of
pyruvate
Pyruvic acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell.
Pyruvic aci ...
.
Salts and
esters of oxamic acid are known collectively as oxamates.
Oxamate is a competitive 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.
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.
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
Lactate may refer to:
* Lactation, the secretion of milk from the mammary glands
* Lactate, the conjugate base of lactic acid
Lactic acid is an organic acid. It has a molecular formula . It is white in the solid state and it is miscible with ...
, oxamate can be used to counterbalance the side effects of phenformin.
Oxamate also plays inhibiting roles with
oxaloacetate, an important intermediate for the
citric acid cycle. Oxamate competes and binds to the
carboxyl transferase domain
In molecular biology, proteins containing the carboxyl transferase domain include biotin-dependent carboxylases. This domain carries out the following reaction: transcarboxylation from biotin to an acceptor molecule. There are two recognised type ...
active site, and reverses the reaction of oxalaoacetate decarboxylation by
pyruvate carboxylase.
References
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Carboxylate anions
Amides