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Usage

Uses

Used in Pharmaceutical Industry:
19-Noretiocholanolone glucuronide is used as a biomarker for the detection and monitoring of nandrolone use in sports and anti-doping efforts. Its presence in urine samples can indicate the misuse of nandrolone, which is a banned anabolic steroid.
Used in Research and Development:
19-Noretiocholanolone glucuronide is used as a research compound for studying the metabolism, pharmacokinetics, and pharmacodynamics of nandrolone and its metabolites. This information can be valuable for understanding the effects of nandrolone on the body and developing new therapeutic strategies.
Used in Clinical Diagnostics:
19-Noretiocholanolone glucuronide can be used as a diagnostic tool in clinical settings to identify and monitor the use of nandrolone in patients. This can be particularly useful in cases where nandrolone is prescribed for medical purposes, and its levels need to be monitored for safety and efficacy.

Upstream product

• 434-22-0 19-nortestosterone 
• 2616-64-0 UDP-glucuronic acid 
• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1225-01-0 19-Norandrosterone 

Relevant academic research and scientific papers

Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites

Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation reactions were 13-28% for most compounds, but significantly higher (77-78%) for the substrates with 4-ene-3-one double bond system of the steroid A-ring. Characterization of glucuronide-conjugated AAS structures was based on nuclear magnetic resonance spectroscopy (1H NMR) and on liquid chromatographic-mass spectrometric (LC-MS) and tandem mass spectrometric (LC-MS/MS) analyses in positive and negative ion mode electrospray ionization (ESI). Only minor differences were observed in optimal synthesis conditions between various substrates, which offer a potential to apply this in vitro assay as a default method for glucuronidation of new AAS substrates. The method allowed for a rapid production pathway of stereochemically pure AAS glucuronides in milligram amount, such as needed, e.g. in the development of analytical methods in forensic or pharmaceutical sciences, as well as in doping control.

Mass spectrometry of steroid glucuronide conjugates. I. Electron impact fragmentation of 5α-/5β-androstan-3α-ol-17-one glucuronides, 5α-estran-3α-ol-17-one glucuronide and deuterium-labelled analogues

Owing to the developments of analytical instruments and interfaces (e.g. coupling high-performance liquid chromatography to mass spectrometry), there has been increased interest in new reference materials, for example in doping analysis with steroid glucuronide conjugates. The synthesized reference material has to pass several characterization steps including the use of gas chromatography/mass spectrometry (GC/MS) for its structure confirmation. In the present study, the fragmentation and mass spectrometric behaviour of several steroid glucuronide conjugates of endogenous and anabolic steroids after derivatization to pertrimethylsilylated products and to methyl ester pertrimethylsilylated products were investigated using GC/MS ion trap and GC/MS quadrupole instruments. The mass spectra of the derivatives of androsterone glucuronide, d5-androsterone glucuronide, epiandrosterone glucuronide, etiocholanolone glucuronide, 11β-hydroxy etiocholanolone glucuronide, 19-norandrosterone glucuronide, d4-19-norandrosterone glucuronide and 1α-methyl-5α-androstan-3α-ol-17-one glucuronide are presented and the origin of typical fragment ions of the glycosidic and steroidal moieties is proposed, based on different derivatization techniques including derivatization with d18-bistrimethylsilylacetamide, methyl ester and trimethylsilyl ester derivatization and selected reaction monitoring. Typical fragmentation patterns which are related to the steroid structure are discussed. Copyright