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Equine in vivo metabolite profiling of the selective androgen receptor modulator LGD-3303 for doping control
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.ORCID iD: 0000-0002-2846-8938
Univ Calif Davis, Sch Vet Med, Kenneth L Maddy Equine Analyt Pharmacol Lab, Davis, CA 95616 USA..
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
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2023 (English)In: Journal of Pharmaceutical and Biomedical Analysis, ISSN 0731-7085, E-ISSN 1873-264X, Vol. 233, article id 115468Article in journal (Refereed) Published
Abstract [en]

LGD-3303 is a Selective Androgen Receptor Modulator (SARM) that is prohibited in both equine and human sports due to its anabolic properties. The aim of this study was to investigate the equine in vivo metabolite profile of LGD-3303 and identify drug metabolites that can be suitable as new and improved analytical targets for equine doping control. This was performed by an oral administration of 0.05 mg.kg(-1) LGD-3303 to horses, where blood and urine samples were collected up to 96 h after administration. The in vivo samples consisting of plasma, urine and hydrolyzed urine were analyzed utilizing ultra-high performance liquid chromatography hyphenated to a Q Exactive (TM) Orbitrap (TM) high resolution mass spectrometer with a heated electrospray ionization source. A total of eight metabolites of LGD-3303 were tentatively identified, including one carboxylated and several hydroxylated metabolites in combination with glucuronic acid conjugates. A monohydroxylated metabolite is suggested as an analytical target for doping control analysis of plasma and urine after hydrolysis with beta-glucuronidase, due to the high intensity and prolonged detection time in comparison to parent LGD-3303.

Place, publisher, year, edition, pages
Elsevier, 2023. Vol. 233, article id 115468
Keywords [en]
Mass spectrometry, Selective androgen receptor modulator, LGD-3303, Doping control, Metabolites, Equine
National Category
Analytical Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-507451DOI: 10.1016/j.jpba.2023.115468ISI: 001008240000001PubMedID: 37224728OAI: oai:DiVA.org:uu-507451DiVA, id: diva2:1781128
Available from: 2023-07-07 Created: 2023-07-07 Last updated: 2024-02-05Bibliographically approved
In thesis
1. Metabolite Profiling of Drugs using Mass Spectrometry: Identification of analytical targets for doping control and improvements of the metabolite search process
Open this publication in new window or tab >>Metabolite Profiling of Drugs using Mass Spectrometry: Identification of analytical targets for doping control and improvements of the metabolite search process
2024 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Doping is defined as the use of prohibited substances or methods by the World Anti-Doping Agency and the aim with doping control analysis is to detect the use of these illicit substances or methods. Substances that are prohibited in human or equine sports have either a positive or negative impact on the performance. Since administered drugs generally are metabolized to a varying degree and thereby not only excreted in their original form, their metabolite profiles are of high interest because drug metabolites may be present in the body for a longer time than the administered drug itself. Thereby detection of metabolites can improve the window of detection. Unfortunately, the metabolite profiles of non-approved drugs that are mainly available on the Internet, such as Selective Androgen Receptor Modulators (SARMs) are often unknown. 

This thesis consists of four papers that all encompass drug metabolite profiling either in vivo, in vitro or in a combination, utilizing separation with liquid chromatography and detection with high resolution mass spectrometry. In paper I and II, the equine in vivo metabolite profiles of the two SARMs ACP-105 and LGD-3303 were investigated and the results showed that using drug metabolites as analytical targets can prolong the detection time. For ACP-105, the in vivo metabolite profile was compared with different incubation models such as liver microsomes, S9 fractions and the fungus Cunninghamella elegans. The in vivo and in vitro metabolite profiles showed an interesting overlap for several metabolites, demonstrating the importance and usefulness for in vitro methods in doping control, especially since microsome incubates are allowed as reference material. An optimization of microsome incubation conditions utilizing experimental design was presented in paper III and IV, showing that the optimized conditions greatly impacted the yield of drug metabolites, but also that the optimal conditions are substance dependent. In paper III, a multivariate data analysis search tool utilizing OPLS-DA was presented, which greatly simplified the in vitro drug metabolite identification process of ACP-105 and the results showed relevance in comparison with human in vivo metabolites.

In conclusion, several new analytical targets with improved detectability for equine and human doping control have been presented, where the drug metabolite profile showed to be of great importance. All together, these new analytical targets, the optimized microsome incubation conditions for improved metabolite yield and the search tool that aids the metabolite investigation through multivariate data analysis, have made a positive contribution to the doping control area.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2024. p. 47
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 1651-6192 ; 348
Keywords
Mass spectrometry, UHPLC-HRMS, Doping control, Metabolite profile, SARM, Selective Androgen Receptor Modulator, MVDA, Microsomes, Experimental design
National Category
Pharmaceutical Sciences Analytical Chemistry
Research subject
Analytical Pharmaceutical Chemistry
Identifiers
urn:nbn:se:uu:diva-521781 (URN)978-91-513-2031-1 (ISBN)
Public defence
2024-03-22, room B42, BMC, Husargatan 3, Uppsala, 09:15 (English)
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Supervisors
Available from: 2024-02-29 Created: 2024-02-05 Last updated: 2024-02-29

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