Aglucuronide, also known asglucuronoside, is any substance produced by linkingglucuronic acid to another substance via aglycosidic bond.[1] The glucuronides belong to theglycosides.
Glucuronidation, the conversion of chemical compounds to glucuronides, is a method that animals use to assist in the excretion of toxic substances, drugs or other substances that cannot be used as anenergy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher watersolubility than the original substance, is eventually excreted by thekidneys.[2]
Enzymes that cleave the glycosidic bond of a glucuronide are calledglucuronidases.
Carboxylic acids are a common functional group in many medications, such asNSAIDS,anticonvulsants, anddiuretics. One common pathway for the clearance of carboxylic-acid-containing drugs is via glucuronidation. By conjugating one such drug to a glucuronide, the resulting compound should be less toxic and exhibit rapid clearance from the body. Manyin vitro studies have provided compelling evidence to suggest, however, that acyl glucuronidation could have adverse pharmalogical effects due to protein adduction. Two mechanisms in which acyl glucuronides lead to protein adduction are: transacylation of the 1-O-β-glucuronide and glycation of the 3-O-β-glucuronide.[3]
Glucuronidation of nitrogen-containing compounds generally form quaternary ammonium-linked glucuronides.Nicotine, which contains a pyridine ring and a pyrrolidine ring,[4] is conjugated at the pyridine nitrogen during drug metabolism. There are two enantiomers of nicotine: S(-)-nicotine and R(+)-nicotine. S(-)-nicotine is the more common stereoisomer of the compound, primarily forming through combustion of nicotine-containing drugs. The S(-)-nicotineN1-glucuronide has a lower Km and higher Vmax for liver microsomes than the N(+)-nicotineN1-glucuronide, suggesting that the body has evolved to favor the eradication of the more common N-linked moiety[5]
{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link).svg) | Thisbiochemistry article is astub. You can help Wikipedia byexpanding it. |
 | Thistoxicology-related article is astub. You can help Wikipedia byexpanding it. |