Identification of hydroxyropivacaine glucuronide in equine urine by ESI+/MS/MS.
Abstract: Ropivacaine is a local anesthetic that has a high potential for abuse in racing horses. It can be recovered from urine collected after administration as a hydroxylated metabolite following beta-glucuronidase treatment of the urine. Based on these findings, it has been inferred that ropivacaine is present in equine urine as a glucuronide metabolite; however, these metabolites have never been directly identified. Using ESI+/MS/MS, the presence of a [M+H]+ molecular ion of m/z 467 was demonstrated in urine corresponding to the calculated mass of a hydroxyropivacaine glucuronide +1. The abundance of this ion diminished after glucuronidase treatment with concomitant appearance of a m/z 291 peak, which is consistent with its hydrolysis to hydroxyropivacaine. In further work, the m/z 467 material was fragmented in the MS/MS system, yielding fragments interpretable as hydroxyropivacaine glucuronide. These data are consistent with the presence of a hydroxyropivacaine glucuronide in equine urine and constitute the first direct demonstration of a specific glucuronide metabolite in equine urine.
Publication Date: 2000-08-10 PubMed ID: 10935884PubMed Central: PMC1189610
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- Journal Article
- Research Support
- Non-U.S. Gov't
Summary
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The research looked into the presence of a specific drug, ropivacaine, and its metabolite, hydroxyropivacaine glucuronide, in horses’ urine. Using advanced scientific techniques, evidence of this drug was found which could help prevent its misuse in competitive horse racing.
Understanding Ropivacaine and its Importance
- Ropivacaine is a local anesthetic that can be misused in horse racing for performance enhancement, which is a significant concern in the sporting world.
- The study aims to identify a particular metabolite of ropivacaine, called hydroxyropivacaine glucuronide, in equine urine. Metabolites are substances needed for or produced from metabolism.
- Existing research suggests the presence of hydroxyropivacaine glucuronide in equine urine following ropivacaine administration, but this has not been directly proven.
Methodology of the Study
- The researchers used Electrospray Ionization Tandem Mass Spectrometry (ESI+/MS/MS), an advanced laboratory technique, for this investigation.
- This method demonstrated a specific molecular ion (m/z 467) in the urine that matches the calculated mass of the hydroxyropivacaine glucuronide. The m/z value refers to the mass-to-charge ratio.
- After a glucuronidase treatment of the urine sample, which meant breaking down the glucuronide, the abundance of the m/z 467 ion decreases and a new m/z 291 peak appears, which aligns with hydroxyropivacaine; this indicates that the treatment successfully dissolved the glucuronide into its original substance.
Significance and Findings
- The abundance of the m/z 467 ion, which represents hydroxyropivacaine glucuronide, and the subsequent appearance of the m/z 291 peak after glucuronidase treatment, provides substantial evidence of the presence of ropivacaine and its metabolite in the urine.
- The fragmentation of the m/z 467 ion in further tests yielded fragments that align with the structure of the glucuronide, supporting the theory of its presence in horse urine.
- This study presents the first direct proof of a specific glucuronide metabolite of ropivacaine in equine urine, an essential step towards controlling drug misuse in horse racing.
Cite This Article
APA
Harkins JD, Karpiesiuk W, Tobin T, Dirikolu L, Lehner AF.
(2000).
Identification of hydroxyropivacaine glucuronide in equine urine by ESI+/MS/MS.
Can J Vet Res, 64(3), 178-183.
Publication
Researcher Affiliations
- Maxwell H Gluck Equine Research Center and the Department of Veterinary Science, University of Kentucky, Lexington 40506-0099, USA. dharkins@ca.uky.edu
MeSH Terms
- Amides / administration & dosage
- Amides / urine
- Anesthetics, Local / administration & dosage
- Anesthetics, Local / urine
- Animals
- Female
- Glucuronides / urine
- Horses / physiology
- Mass Spectrometry
- Ropivacaine
- Substance-Related Disorders
References
This article includes 5 references
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- Harkins JD, Lehner A, Karpiesiuk W, Woods WE, Dirikolu L, Boyles J, Carter WG, Tobin T. Bupivacaine in the horse: relationship of local anaesthetic responses and urinary concentrations of 3-hydroxybupivacaine.. J Vet Pharmacol Ther 1999 Jun;22(3):181-95.
- Harkins JD, Karpiesiuk W, Woods WE, Lehner A, Mundy GD, Rees WA, Dirikolu L, Bass S, Carter WG, Boyles J, Tobin T. Mepivacaine: its pharmacological effects and their relationship to analytical findings in the horse.. J Vet Pharmacol Ther 1999 Apr;22(2):107-21.
- Harkins JD, Mundy GD, Woods WE, Lehner A, Karpiesiuk W, Rees WA, Dirikolu L, Bass S, Carter WG, Boyles J, Tobin T. Lidocaine in the horse: its pharmacological effects and their relationship to analytical findings.. J Vet Pharmacol Ther 1998 Dec;21(6):462-76.
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