165195-35-7

Usage

Uses

Used in Pharmaceutical Research:
4-Androsten-17α-ol-3-one-2,2,4,6,6-d5 is used as a research compound in the pharmaceutical industry for the development and optimization of drugs targeting the androgen receptor. Its isotopically labeled nature allows for the tracking and analysis of its metabolic pathways and interactions with enzymes, providing valuable insights into the mechanisms of action and potential side effects of new drug candidates.
Used in Metabolic Studies:
In the field of biochemistry and molecular biology, 4-Androsten-17α-ol-3-one-2,2,4,6,6-d5 is employed as a tracer molecule to study the metabolism of steroid hormones. The incorporation of deuterium atoms into the compound enables researchers to monitor its metabolic fate and identify the enzymes and pathways involved in its metabolism, which can contribute to a better understanding of hormonal regulation and the development of metabolic disorders.
Used in Enzyme Activity Assays:
4-Androsten-17α-ol-3-one-2,2,4,6,6-d5 is utilized as a substrate in enzyme activity assays to evaluate the function and specificity of enzymes involved in steroid hormone metabolism. The deuterated compound can be used to differentiate between the activities of various enzymes and to study the kinetics of enzymatic reactions, providing valuable information for the development of targeted therapies and the elucidation of metabolic pathways.
Used in Mass Spectrometry:
In analytical chemistry, 4-Androsten-17α-ol-3-one-2,2,4,6,6-d5 is employed as an internal standard in mass spectrometry for the quantification and identification of steroid hormones and their metabolites. The presence of deuterium atoms in the compound provides a distinct mass signature, allowing for accurate measurement and comparison of the target analytes in complex biological samples.
Used in Sports Doping Control:
4-Androsten-17α-ol-3-one-2,2,4,6,6-d5 is also used in the field of sports anti-doping as a reference compound for the detection and quantification of anabolic steroids in athletes' urine samples. The isotopically labeled nature of the compound helps to distinguish between endogenous and exogenous sources of steroids, aiding in the identification of doping violations and ensuring fair competition in sports.

Upstream product

• 79037-28-8 [1α,2α-2H2]androst-4-ene-3,17-dione 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 4273-45-4 [1α,2,2,4,6,6,16,16-2H8]androst-4-ene-3,17-dione 
• 58-22-0 testosterone 

Downstream Products

• 638163-38-9 [1α,16,16,17α-2H4]androst-4-en-6β,17β-diol-3-one 
• 638163-36-7 [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one 

Relevant academic research and scientific papers

SYNTHESIS OF 5-EPITESTOSTERONE

Isotopically pure d5-epitestosterone has been synthesized for the first time.This polydeuterated 17α-hydroxyandrosterone was prepared by H/D exchange reaction with MeOD-D2O under basic conditions.Its characteristics are described in detail, including its enolization into a d4-heterodienic silyl ether derivative upon silylation.Keywords: 5-17α-Hydroxyandrost-4-en-3-one, d5-epitestosterone, deuteration, labeling, synthesis, dienolsilyl ether

Synthesis of stable isotope labelled internal standards for drug-drug interaction (DDI) studies

The syntheses of stable isotope labelled internal standards of important CYP-isoform selective probes, like testosterone 1, diclofenac 3, midazolam 5, and dextromethorphan 7, as well as their corresponding hydroxylated metabolites 6β-hydroxytestosterone 2

Syntheses of stable isotope-labeled 6β-hydroxycortisol, 6β-hydroxycortisone, and 6β-hydroxytestosterone

A method is described for the preparation of two types of multi-labeled 6β-hydroxycortisol containing either five deuterium atoms at C-19 methyl and C-1 methylene or four 13C atoms at C-1, C-2, C-4, and C-19 in addition to the five deuterium atoms for use as analytical internal standards for gas chromatography-mass spectrometry (GC-MS). BMD derivatives of [1,1,19,19,19-2H5]cortisone and [1,2,4,19- 13C4,1,1,19,19,19-2H5]cortisone (cortisone-2H5-BMD and cortisone-13C 4,2H5-BMD) were first synthesized via indan synthon method starting from optical active 11-oxoindanylpropionic acid and labeled isopropenyl anion ([1,1,3,3,3-2H5]- or [1,3- 13C2,1,1,3,3,3-2H5]isopropenyl anion). The labeled isopropenyl anion was prepared from commercially available [1,1,1,3,3,3-2H6]- or [1,3-13C 2,1,1,1,3,3,3-2H6]acetone. Ultraviolet (UV) irradiated autoxidation at C-6 position of 3-ethyl-3,5-dienol ether derivatives of the labeled cortisone-BMDs gave 6β-hydroxy-[1,1,19,19,19- 2H5]cortisone-BMD and 6β-hydroxy-[1,2,4,19- 13C4,1,1,19,19,19-2H5]cortisone-BMD, respectively, as a mixture of 6β- and 6α-epimers in a ratio of 4:1. Separation of 6β- and 6α-epimers by thin-layer chromatography (TLC) and subsequent hydrolysis of the BMD group at C-17 gave pure labeled 6β-hydroxycortisone. After protecting the keto group at C-3 of the labeled 6β-hydroxycortisone-BMD as semicarbazone, reduction of 11-keto group with NaBH4 and subsequent removal of the C-3 and C-17 protecting groups gave 6β-hydroxy-[1,1,19,19,19-2H5]cortisol (6β-hydroxycortisol-2H5) and 6β -hydroxy-[1,2,4,19-13C4,1,1,19,19,19-2H 5]cortisol (6β-hydroxycortisol-13C4, 2H5), respectively, as a mixture of 6β- and 6α-epimers (6β:6α=4.4:1). The isotopic compositions of 6β-hydroxycortisol-2H5 and 6β -hydroxycortisol-13C4,2H5 were 90.9 and 92.1 at.%, respectively. Furthermore, 6β-hydroxy-[1α ,16,16,17α-2H4]testosterone was synthesized by the UV irradiated autoxidation at C-6 position of 3-ethyl-3,5-dienol ether derivative of deuterium-labeled testosterone ([1α,16,16,17α- 2H4]testosterone) obtained by using catalytic deuteration and hydrogen-deuterium exchange reactions.