5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity

Publikationen: Beitrag in Buch/Bericht/KonferenzbandKonferenzbeitrag - Aufsatz in KonferenzbandForschung

Standard

5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity. / Müller, Dennis; Opfermann, Georg; Rojas, Sandra; Schlörer, Nils; Pokrywka, Andrzej; Kwiatkowska, Dorota; Diel, Patrick; Schänzer, Wilhelm; Parr, Maria Kristina.

Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante. Hrsg. / Wilhelm Schänzer; Mario Thevis; Hans Geyer; Ute Mareck. Sportverlag Strauß, 2012. S. 197-200 (Recent advances in doping analysis; Band 20).

Publikationen: Beitrag in Buch/Bericht/KonferenzbandKonferenzbeitrag - Aufsatz in KonferenzbandForschung

Harvard

Müller, D, Opfermann, G, Rojas, S, Schlörer, N, Pokrywka, A, Kwiatkowska, D, Diel, P, Schänzer, W & Parr, MK 2012, 5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity. in W Schänzer, M Thevis, H Geyer & U Mareck (Hrsg.), Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante. Recent advances in doping analysis, Bd. 20, Sportverlag Strauß, S. 197-200, Cologne Workshop on Dope Analysis, Köln, Deutschland, 26.02.12.

APA

Müller, D., Opfermann, G., Rojas, S., Schlörer, N., Pokrywka, A., Kwiatkowska, D., Diel, P., Schänzer, W., & Parr, M. K. (2012). 5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity. in W. Schänzer, M. Thevis, H. Geyer, & U. Mareck (Hrsg.), Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante (S. 197-200). (Recent advances in doping analysis; Band 20). Sportverlag Strauß.

Vancouver

Müller D, Opfermann G, Rojas S, Schlörer N, Pokrywka A, Kwiatkowska D et al. 5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity. in Schänzer W, Thevis M, Geyer H, Mareck U, Hrsg., Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante. Sportverlag Strauß. 2012. S. 197-200. (Recent advances in doping analysis).

Bibtex

@inbook{70a47bf268b34c43b485dfc18699aec0,
title = "5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity",
abstract = "5α-Androst-1-ene-3,17-dione (1-AD) is listed on the World Anti-Doping Agency{\textquoteright}s prohibited list as an “exogenous anabolic androgenic steroid”. It could be marketed in dietary supplements. An excretion study was conducted with six male volunteers, to whom were orally administered 50 mg of 1-AD in one-time application. Urine samples were collected for two weeks. The metabolites were measured as TMS-derivatives with GC/MS. The intake was detectable up to eight days based on the main metabolite 3α-hydroxy-5α-androst-1-en-17-one (1-DHA). 1-DHA was synthesized from 5α-androst-2-en-17-one via the 2,3-epoxid as an intermediate and structurally identified with GC/MS and NMR. Other identified metabolites were 17β-hydroxy-5α-androst-1-en-3-one (1-testosterone), 5α-androst-1-ene-3α,17β-diol and 5α-androst-1-ene-3β,17β-diol. Furthermore two additional metabolites, presumably 18-hydroxy-5α-androst-1-ene-3,17-dione and 19-hydroxy-5α-androst-1-ene-3,17-dione, but until now without final confirmation, as well as the parent compound, were detectable in the urine. Ratios in the endogenous urinary steroid profile typically evaluated for doping analysis were also altered. Androsterone/etiocholanolone ratio (AND/ETIO) and 5α-/5β-androstane-3α,17β-diol ratio (Adiol/Bdiol) were increased. But there were no changes in the testosterone/epitestosterone quotient. The parent substance 1-AD, the main metabolite 1-DHA, 1-testosterone and 3β-hydroxy-5α-androst-1-en-17-one (1-DHEA) were also tested in the yeast-androgen-screen, a test system for androgen receptor-mediated gene expression. An androgenic activity could be shown for all. 1-Testosterone was shown to be 10-times more potent than 1-AD and 100-times more potent than the equipotent substances 1-DHA and 1-DHEA. Verf.-Referat",
keywords = "Biochemie, Doping, Dopinganalyse, Dopingnachweis, Epitestosteron, Gaschromatographie, Massenspektrometrie, Metabolit, Screening, Steroid, Testosteron, Untersuchungsmethode, Urin, Urinausscheidung, Urinuntersuchung",
author = "Dennis M{\"u}ller and Georg Opfermann and Sandra Rojas and Nils Schl{\"o}rer and Andrzej Pokrywka and Dorota Kwiatkowska and Patrick Diel and Wilhelm Sch{\"a}nzer and Parr, {Maria Kristina}",
year = "2012",
language = "English",
series = "Recent advances in doping analysis",
publisher = "Sportverlag Strau{\ss}",
pages = "197--200",
editor = "Wilhelm Sch{\"a}nzer and Mario Thevis and Hans Geyer and Ute Mareck",
booktitle = "Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante",
note = "Cologne Workshop on Dope Analysis ; Conference date: 26-02-2012 Through 02-03-2012",

}

RIS

TY - CHAP

T1 - 5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity

AU - Müller, Dennis

AU - Opfermann, Georg

AU - Rojas, Sandra

AU - Schlörer, Nils

AU - Pokrywka, Andrzej

AU - Kwiatkowska, Dorota

AU - Diel, Patrick

AU - Schänzer, Wilhelm

AU - Parr, Maria Kristina

N1 - Conference code: 30

PY - 2012

Y1 - 2012

N2 - 5α-Androst-1-ene-3,17-dione (1-AD) is listed on the World Anti-Doping Agency’s prohibited list as an “exogenous anabolic androgenic steroid”. It could be marketed in dietary supplements. An excretion study was conducted with six male volunteers, to whom were orally administered 50 mg of 1-AD in one-time application. Urine samples were collected for two weeks. The metabolites were measured as TMS-derivatives with GC/MS. The intake was detectable up to eight days based on the main metabolite 3α-hydroxy-5α-androst-1-en-17-one (1-DHA). 1-DHA was synthesized from 5α-androst-2-en-17-one via the 2,3-epoxid as an intermediate and structurally identified with GC/MS and NMR. Other identified metabolites were 17β-hydroxy-5α-androst-1-en-3-one (1-testosterone), 5α-androst-1-ene-3α,17β-diol and 5α-androst-1-ene-3β,17β-diol. Furthermore two additional metabolites, presumably 18-hydroxy-5α-androst-1-ene-3,17-dione and 19-hydroxy-5α-androst-1-ene-3,17-dione, but until now without final confirmation, as well as the parent compound, were detectable in the urine. Ratios in the endogenous urinary steroid profile typically evaluated for doping analysis were also altered. Androsterone/etiocholanolone ratio (AND/ETIO) and 5α-/5β-androstane-3α,17β-diol ratio (Adiol/Bdiol) were increased. But there were no changes in the testosterone/epitestosterone quotient. The parent substance 1-AD, the main metabolite 1-DHA, 1-testosterone and 3β-hydroxy-5α-androst-1-en-17-one (1-DHEA) were also tested in the yeast-androgen-screen, a test system for androgen receptor-mediated gene expression. An androgenic activity could be shown for all. 1-Testosterone was shown to be 10-times more potent than 1-AD and 100-times more potent than the equipotent substances 1-DHA and 1-DHEA. Verf.-Referat

AB - 5α-Androst-1-ene-3,17-dione (1-AD) is listed on the World Anti-Doping Agency’s prohibited list as an “exogenous anabolic androgenic steroid”. It could be marketed in dietary supplements. An excretion study was conducted with six male volunteers, to whom were orally administered 50 mg of 1-AD in one-time application. Urine samples were collected for two weeks. The metabolites were measured as TMS-derivatives with GC/MS. The intake was detectable up to eight days based on the main metabolite 3α-hydroxy-5α-androst-1-en-17-one (1-DHA). 1-DHA was synthesized from 5α-androst-2-en-17-one via the 2,3-epoxid as an intermediate and structurally identified with GC/MS and NMR. Other identified metabolites were 17β-hydroxy-5α-androst-1-en-3-one (1-testosterone), 5α-androst-1-ene-3α,17β-diol and 5α-androst-1-ene-3β,17β-diol. Furthermore two additional metabolites, presumably 18-hydroxy-5α-androst-1-ene-3,17-dione and 19-hydroxy-5α-androst-1-ene-3,17-dione, but until now without final confirmation, as well as the parent compound, were detectable in the urine. Ratios in the endogenous urinary steroid profile typically evaluated for doping analysis were also altered. Androsterone/etiocholanolone ratio (AND/ETIO) and 5α-/5β-androstane-3α,17β-diol ratio (Adiol/Bdiol) were increased. But there were no changes in the testosterone/epitestosterone quotient. The parent substance 1-AD, the main metabolite 1-DHA, 1-testosterone and 3β-hydroxy-5α-androst-1-en-17-one (1-DHEA) were also tested in the yeast-androgen-screen, a test system for androgen receptor-mediated gene expression. An androgenic activity could be shown for all. 1-Testosterone was shown to be 10-times more potent than 1-AD and 100-times more potent than the equipotent substances 1-DHA and 1-DHEA. Verf.-Referat

KW - Biochemie

KW - Doping

KW - Dopinganalyse

KW - Dopingnachweis

KW - Epitestosteron

KW - Gaschromatographie

KW - Massenspektrometrie

KW - Metabolit

KW - Screening

KW - Steroid

KW - Testosteron

KW - Untersuchungsmethode

KW - Urin

KW - Urinausscheidung

KW - Urinuntersuchung

M3 - Conference contribution - Article for conference

T3 - Recent advances in doping analysis

SP - 197

EP - 200

BT - Recent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante

A2 - Schänzer, Wilhelm

A2 - Thevis, Mario

A2 - Geyer, Hans

A2 - Mareck, Ute

PB - Sportverlag Strauß

T2 - Cologne Workshop on Dope Analysis

Y2 - 26 February 2012 through 2 March 2012

ER -

ID: 185800