Analytical developments of p-hydroxy prenylamine reference material for dope control research: Characterization and purity assessment.
HPLC
LC-MS/MS
chiral R and S separation
impurity fragmentation
prenylamine metabolite
Journal
Drug testing and analysis
ISSN: 1942-7611
Titre abrégé: Drug Test Anal
Pays: England
ID NLM: 101483449
Informations de publication
Date de publication:
Feb 2022
Feb 2022
Historique:
revised:
20
09
2021
received:
30
03
2021
accepted:
24
09
2021
pubmed:
8
10
2021
medline:
5
4
2022
entrez:
7
10
2021
Statut:
ppublish
Résumé
Prenylamine was initially used for the treatment of angina pectoris and later on withdrawn from the market in 1988 due to cardiac arrhythmias concern. The major phase I metabolite of prenylamine is p-hydroxy prenylamine that has a chiral center in the structure. Even though p-hydroxy prenylamine was synthesized earlier, it lacked complete analytical developments for chiral high-performance liquid chromatography (HPLC) separation. However, p-hydroxy prenylamine reference material is not commercially available. The innovation of this manuscript is the development and validation of a chiral HPLC separation method and more extensive characterization of the reference material than previously reported method. Therefore, it was hypothesized to develop and validate normal phase HPLC method for p-hydroxy prenylamine reference material. p-Hydroxy prenylamine was synthesized in two batches and characterized successfully using
Substances chimiques
Prenylamine
K2OH82Z000
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
224-232Subventions
Organisme : NDTL, New Delhi
Informations de copyright
© 2021 John Wiley & Sons, Ltd.
Références
Houlihan B, Vidar Hanstad D. The effectiveness of the World Anti-Doping Agency: developing a framework for analysis. Int J Sport Policy Polit. 2019;11(2):203-217. https://www.tandfonline.com/doi/abs/10.1080/19406940.2018.1534257
Houlihan B. Achieving compliance in international anti-doping policy: an analysis of the 2009 World Anti-Doping Code. Sport Manag Rev. 2014;17(3):265-276. https://doi.org/10.1016/j.smr.2013.10.002
Docherty JR. Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA). Br J Pharmacol. 2008;154(3):606-622.
Dib J, Mongongu C, Buisson C, et al. Mass spectrometric characterization of the hypoxia-inducible factor (HIF) stabilizer drug candidate BAY 85-3934 (molidustat) and its glucuronidated metabolite BAY-348, and their implementation into routine doping controls. Drug Test Anal. 2017;9(1):61-67.
Pitassi C, de Lacerda LR. Technological capability of doping control laboratories: a metric proposal. Int J Sport Policy Polit. 2019;11(3):539-557. https://doi.org/10.1080/19406940.2018.1528993
Catlin DH, Fitch KD, Ljungqvist A. Medicine and science in the fight against doping in sport. J Intern Med. 2008;264(2):99-114.
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. 2020:1-19. https://doi.org/10.1080/10408347.2020.1788375
“Prohibited List Documents|World Anti-Doping Agency,” Available at: https://www.wada-ama.org/en/resources/science-medicine/prohibited-list-documents, [Last accessed on 26/08/2021 at 4:29PM Indian Time]
Obianwu H. Actions of prenylamine (Segontin ®) on the cardiovascular system. Acta Pharmacol Toxicol (Copenh). 1967;25(1):127-140. https://doi.org/10.1111/j.1600-0773.1967.tb01417.x
Stephenson P, Dewar HA, Newell DJ. A clinical trial of prenylamine lactate (synadrin) in the treatment of angina of effort. Scott Med J. 1963;8(7):279-282.
Oakley D, Jennings K, Puritz R, Krikler D, Chamberlain D. The effect of prenylamine on the QT interval of the resting electrocardiogram in patients with angina pectoris. Postgrad Med J. 1980;56(661):753-756.
Shah RR, Stonier PD. Withdrawal of prenylamine: perspectives on pharmacological, clinical and regulatory outcomes following the first QT-related casualty. Ther Adv Drug Saf. 2018;9(8):475-493.
Lewandowicz J, Starzyński Z. Acute prenylamine poisoning. Arch Toxikol. 1974;31(3):217-222.
Palm D, Fengler H, Grobecker H. Urinary excretion of amphetamine in man after administration of prenylamine. Life Sci. 1969;8(5):247-257.
Kraemer T, Roditis SK, Peters FT, Maurer HH. Amphetamine concentrations in human urine following single-dose administration of the calcium antagonist prenylamine-studies using fluorescence polarization immunoassay (FPIA) and GC-MS. J Anal Toxicol. 2003;27(2):68-73.
Musshoff F. Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine. Drug Metab Rev. 2000;32(1):15-44.
International standard prohibited list 2021, [Last accessed on 26/08/2021 at 4:29PM Indian Time]
Remberg G, Eichelbaum M, Spiteller G, Dengler HJ. Metabolism ofDL-[14C]prenylamine in man. Biol Mass Spectrom. 1977;4(5):297-304. https://doi.org/10.1002/bms.1200040505
Beuck S, Sigmund G, Koch A, et al. Identification and characterization of urinary prenylamine metabolites by means of liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2012;4(9):701-716.
“General chapters: <281> residue on ignition,” Available at: http://www.pharmacopeia.cn/v29240/usp29nf24s0_c281.html, [Last accessed on 26/08/2021 at 4:29PM Indian Time].
“Polarimeter|Protocol,” Available at: https://www.jove.com/v/10348/polarimeter, [Last accessed on 26/08/2021 at 4:29PM Indian Time]
Yanik GW. Polarimeter chiral detectors in enantioseparations. Chiral Sep Tech A Pract Approach, Third Ed. 2007;561-584. https://doi.org/10.1002/9783527611737.ch16
Camont L, Cottart CH, Rhayem Y, et al. Simple spectrophotometric assessment of the trans−/cis-resveratrol ratio in aqueous solutions. Anal Chim Acta. 2009;634(1):121-128.
Branch SK. Guidelines from the international conference on harmonisation (ICH). J Pharm Biomed Anal. 2005;38(5):798-805.
Darwish HW, Ali NA, Naguib IA, El Ghobashy MR, Al-Hossaini AM, Abdelrahman MM. Development and validation of a stability indicating RP-HPLC-DAD method for the determination of bromazepam. PLoS ONE. 2021;16(3):1-12. https://doi.org/10.1371/JOURNAL.PONE.0244951
Rustichelli D, Castiglia S, Gunetti M, et al. Validation of analytical methods in compliance with good manufacturing practice: a practical approach. J Transl Med. 2013;11(1):1-13.