Process development for the total synthesis of the novel drug metabolite Carboxy toremifene as a standard reference material along with characterization and purity assessment for the Antidoping quality Control Purposes.
LC-QTOF
analytical standards
carboxy tamoxifen
dope testing
purity analysis
Journal
Drug testing and analysis
ISSN: 1942-7611
Titre abrégé: Drug Test Anal
Pays: England
ID NLM: 101483449
Informations de publication
Date de publication:
Nov 2022
Nov 2022
Historique:
revised:
11
10
2022
received:
29
03
2022
accepted:
11
10
2022
pubmed:
14
10
2022
medline:
17
12
2022
entrez:
13
10
2022
Statut:
ppublish
Résumé
Tamoxifen and toremifene are two selective estrogen receptor modulators (SERMs) commonly used to treat breast cancer in women. Toremifene is well-known as a triphenylethylene derivative. Carboxy toremifene is a common metabolite of toremifene and tamoxifen. Since 2005, the World Anti-Doping Agency (WADA) has banned the SERMs category during in and out of competition. These substances are in the S4 category in the WADA prohibited list as "agents with anti-oestrogenic activity." However, there is no commercially accessible carboxy toremifene reference material in the market. This research highlights the novel synthetic procedure, the development of a carboxy toremifene HPLC method, and validation, along with detailed characterization using advanced analytical techniques using
Substances chimiques
Toremifene
7NFE54O27T
Selective Estrogen Receptor Modulators
0
Tamoxifen
094ZI81Y45
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2002-2006Subventions
Organisme : NDTL, New Delhi
ID : 249(i)/Admin/NDTL/2020-21
Informations de copyright
© 2022 John Wiley & Sons Ltd.
Références
Handelsman DJ. Indirect androgen doping by oestrogen blockade in sports. Br J Pharmacol. 2008;154(3):598-605. doi:10.1038/bjp.2008.150
Handelsman DJ, Heather A. Androgen abuse in sports. Asian J Androl. 2008;10(3):403-415. doi:10.1111/j.1745-7262.2008.00406.x
Handelsman DJ. The rationale for banning human chorionic gonadotropin and estrogen blockers in sport. J Clin Endocrinol Metab. 2006;91(5):1646-1653. doi:10.1210/jc.2005-2569
Mazzarino M, Fiacco I, De La Torre X, Botrè F. A mass spectrometric approach for the study of the metabolism of clomiphene, tamoxifen, and toremifene by liquid chromatography time-of-flight spectroscopy. Eur J Mass Spectrom. 2008;14(3):171-180. doi:10.1255/ejms.921
Mazzarino M, Bragan MC, De La Torre X, Molaioni F, Botrè F. Relevance of the selective oestrogen receptor modulators tamoxifen, toremifene and clomiphene in doping field: endogenous steroids urinary profile after multiple oral doses. Steroids. 2011;76(12):1400-1406. doi:10.1016/j.steroids.2011.06.005
Mazzarino M, Biava M, de la Torre X, Fiacco I, Botrè F. Characterization of the biotransformation pathways of clomiphene, tamoxifen and toremifene as assessed by LC-MS/(MS) following in vitro and excretion studies. Anal Bioanal Chem. 2013;405(16):5467-5487. doi:10.1007/s00216-013-6961-7
Kangas L. Biochemical and pharmacological effects of toremifene metabolites. Cancer Chemother Pharmacol. 1990;27(1):8-12. doi:10.1007/BF00689269
Webster LK, Crinis NA, Stokes KH, Bishop JF. High-performance liquid chromatographic method for the determination of toremifene and its major human metabolites. J Chromatogr B Biomed Sci Appl. 1991;565(1-2):482-487. doi:10.1016/0378-4347(91)80414-8
Kwok KY, Chan GHM, Kwok WH, Wong JKY, Wan TSM. In vitro phase I metabolism of selective estrogen receptor modulators in horse using ultra-high performance liquid chromatography-high resolution mass spectrometry. Drug Test Anal. 2017;9(9):1349-1362. doi:10.1002/dta.2158
World-Anti Doping Agency. The 2021 WADA prohibited list. World anti-doping 2021, 1-24.
Lu J, Wang X, Xu Y, et al. Mass spectrometric characterization of toremifene metabolites in human urine by liquid chromatography-tandem mass spectrometry with different scan modes. Analyst. 2011;136(3):467-472. doi:10.1039/c0an00487a
Moinuddin SK, Gajbhiye RL, Mehta P, et al. UHPLC-DAD method development and validation: degradation kinetic, stress studies of farnesol and characterization of degradation products using LC-QTOF-ESI-MS with in silico pharmacokinetics and toxicity predictions. J Chromatogr Sci. 2021. doi:10.1093/CHROMSCI/BMAB127
Sharma V, Shaik KM, Choudhury A, et al. Investigations of process parameters during dissolution studies of drug loaded 3D printed tablets. Proc Inst Mech Eng Part H J Eng Med. 2021;235(5):523-529. doi:10.1177/0954411921993582
Shaik KM, Sarmah B, Wadekar GS, Kumar P. Regulatory updates and analytical methodologies for nitrosamine impurities detection in sartans, ranitidine, nizatidine, and metformin along with sample preparation techniques. Crit Rev Anal Chem. 2020;52(1):1-19. doi:10.1080/10408347.2020.1788375
Joseph A, Kumar GJ, Pawar SD, et al. Analytical developments of P-hydroxy prenylamine reference material for dope control research: characterization and purity assessment. Drug Test Anal. 2021;14(2):224-232. doi:10.1002/DTA.3171
Pawar SD, Kumar GJ, Chikkondra A, et al. Synthesis, characterization, method development, and validation of nor-ethylmorphine hydrochloride reference material using established analytical techniques for dope control analysis. Drug Test Anal. 2021;14(2):388-392. doi:10.1002/DTA.3178
Susanna KJ, Gajbhiye R, Sarmah B, et al. Simultaneous method development and validation of anastrozole along with piperine: degradation studies and degradants characterization using LC-QTOF-ESI-MS along with degradants in-silico ADMET predictions. Curr Drug Metab. 2022;23(2):113-130. doi:10.2174/1389200223666220215152606