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[PMID]:26699683
[Au] Autor:Piper T; Schänzer W; Thevis M
[Ad] Endereço:German Sport University Cologne, Center for Preventive Doping Research-Institute of Biochemistry, Am Sportpark Müngersdorf 6, 50933 Köln, Germany. Electronic address: t.piper@biochem.dshs-koeln.de.
[Ti] Título:Revisiting the metabolism of 19-nortestosterone using isotope ratio and high resolution/high accuracy mass spectrometry.
[So] Source:J Steroid Biochem Mol Biol;162:80-91, 2016 09.
[Is] ISSN:1879-1220
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The synthetic anabolic androgenic steroid 19-nortestosterone is prohibited in sports according to the regulations of the World Anti-Doping Agency (WADA) due to its performance-enhancing effects. Today, doping controls focus predominantly on one main urinary metabolite, 19-norandrosterone glucuronide, which offers the required detection windows for an appropriate retrospectivity of sports drug testing programs. As 19-norandrosterone can also be found in urine at low concentrations originating from in situ demethylation of other abundant steroids or from endogenous production, the exogenous source of 19-norandrosterone needs to be verified, which is commonly accomplished by carbon isotope ratio analyses. The aim of this study was to re-investigate the metabolism of 19-nortestosterone in order to probe for additional diagnostic long-term metabolites, which might support the unambiguous attribution of an endo- or exogenous source of detected 19-nortestosterone metabolites. Employing a recently introduced strategy for metabolite identification, threefold deuterated 19-nortestosterone (16,16,17-(2)H3-NT) was administered to one healthy male volunteer and urine samples were collected for 20 days. Samples were prepared with established methods separating unconjugated, glucuronidated and sulfated steroids, and analytes were further purified by means of high-performance liquid chromatography before trimethylsilylation. Deuterated metabolites were identified using gas chromatograph/thermal conversion/isotope ratio mass spectrometer comprising an additional single quadrupole mass spectrometer. Additional structural information was obtained by gas chromatography/time-of-flight mass spectrometry and liquid chromatography/high resolution mass spectrometry. In general, sulfo-conjugated metabolites were excreted for a longer time period than the corresponding glucuronides. Several unexpected losses of the arguably stable isotope labels were observed and characterized, attributed to metabolic reactions and sample preparation procedures. The detection window of one of the newly detected metabolites was higher than currently used metabolites. The suitability of this metabolite to differentiate between endo- or exogenous sources could however not be verified conclusively.
[Mh] Termos MeSH primário: Anabolizantes/metabolismo
Anabolizantes/urina
Cromatografia Líquida de Alta Pressão/métodos
Estranos/metabolismo
Estranos/urina
Espectrometria de Massas em Tandem/métodos
[Mh] Termos MeSH secundário: Administração Oral
Adulto
Anabolizantes/administração & dosagem
Cromatografia Gasosa/métodos
Doping nos Esportes
Estranos/administração & dosagem
Seres Humanos
Masculino
Substâncias para Melhoria do Desempenho/administração & dosagem
Substâncias para Melhoria do Desempenho/metabolismo
Substâncias para Melhoria do Desempenho/urina
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Anabolic Agents); 0 (Estranes); 0 (Performance-Enhancing Substances); 5W4XKU708V (19-norandrosterone)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151225
[St] Status:MEDLINE


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[PMID]:26480899
[Au] Autor:Palermo A; Alessi B; Botrè F; de la Torre X; Fiacco I; Mazzarino M
[Ad] Endereço:Laboratorio Antidoping, Federazione Medico Sportiva Italiana, Largo Giulio Onesti, 1, 00197, Rome, Italy.
[Ti] Título:In vitro evaluation of the effects of anti-fungals, benzodiazepines and non-steroidal anti-inflammatory drugs on the glucuronidation of 19-norandrosterone: implications on doping control analysis.
[So] Source:Drug Test Anal;8(9):930-9, 2016 Sep.
[Is] ISSN:1942-7611
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:We have studied whether the phase II metabolism of 19-norandrosterone, the most representative metabolite of 19-nortestosterone (nandrolone), can be altered in the presence of other drugs that are not presently included on the Prohibited List of the World Anti-Doping Agency. In detail, we have evaluated the effect of non-prohibited drugs belonging to the classes of anti-fungals, benzodiazepines, and non-steroidal anti-inflammatory drugs on the glucuronidation of 19-norandrosterone. In vitro assays based on the use of either pooled human liver microsomes or specific recombinant isoforms of uridine diphosphoglucuronosyl-transferase were designed and performed to monitor the formation of 19-norandrosterone glucuronide from 19-norandrosterone. Determination of 19-norandrosterone (free and conjugated fraction) was performed by gas chromatography - mass spectrometry after sample pretreatment consisting of an enzymatic hydrolysis (performed only for the conjugated fraction), liquid/liquid extraction with tert-butylmethyl ether, and derivatization to form the trimethylsilyl derivative. In parallel, a method based on reversed-phase liquid chromatography coupled to tandem mass spectrometry in positive electrospray ionization with acquisition in selected reaction monitoring mode was also developed to identify the non-prohibited drugs considered in this study. Incubation experiments have preliminarily shown that the glucuronidation of 19-norandrosterone is principally carried out by UGT2B7 (39%) and UGT2B17 (31%). Inhibition studies have shown that the yield of the glucuronidation reaction is reduced in the presence of the anti-fungals itraconazole, ketoconazole, and miconazole, of the benzodiazepine triazolam and of the non-steroidal anti-inflammatory drugs diclofenac and ibuprofen, while no alteration was recorded in the presence of all other compounds considered in this study. Copyright © 2015 John Wiley & Sons, Ltd.
[Mh] Termos MeSH primário: Anti-Inflamatórios não Esteroides/metabolismo
Antifúngicos/metabolismo
Benzodiazepinas/metabolismo
Estranos/metabolismo
Glucuronídeos/metabolismo
[Mh] Termos MeSH secundário: Cromatografia Líquida
Doping nos Esportes
Interações Medicamentosas
Cromatografia Gasosa-Espectrometria de Massas
Glucuronosiltransferase/metabolismo
Seres Humanos
Microssomos Hepáticos/efeitos dos fármacos
Microssomos Hepáticos/metabolismo
Antígenos de Histocompatibilidade Menor/metabolismo
Isoformas de Proteínas/metabolismo
Detecção do Abuso de Substâncias
Espectrometria de Massas em Tandem
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Inflammatory Agents, Non-Steroidal); 0 (Antifungal Agents); 0 (Estranes); 0 (Glucuronides); 0 (Minor Histocompatibility Antigens); 0 (Protein Isoforms); 12794-10-4 (Benzodiazepines); 5W4XKU708V (19-norandrosterone); EC 2.4.1.- (UGT2B7 protein, human); EC 2.4.1.17 (Glucuronosyltransferase); EC 2.4.1.17 (UGT2B17 protein, human)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151021
[St] Status:MEDLINE
[do] DOI:10.1002/dta.1897


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[PMID]:25732071
[Au] Autor:Schneider G; Görbe T; Mernyák E; Wölfling J; Holczbauer T; Czugler M; Sohár P; Minorics R; Zupkó I
[Ad] Endereço:Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary. Electronic address: schneider@chem.u-szeged.hu.
[Ti] Título:Synthesis of novel 17-(5'-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro.
[So] Source:Steroids;98:153-65, 2015 Jun.
[Is] ISSN:1878-5867
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17ß-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.
[Mh] Termos MeSH primário: Antineoplásicos
Cobre/química
Citotoxinas
Estranos
Hidrocarbonetos Iodados
[Mh] Termos MeSH secundário: Antineoplásicos/síntese química
Antineoplásicos/química
Antineoplásicos/farmacologia
Catálise
Citotoxinas/síntese química
Citotoxinas/química
Citotoxinas/farmacologia
Ensaios de Seleção de Medicamentos Antitumorais
Estranos/síntese química
Estranos/química
Estranos/farmacologia
Células HeLa
Seres Humanos
Hidrocarbonetos Iodados/síntese química
Hidrocarbonetos Iodados/química
Hidrocarbonetos Iodados/farmacologia
Células MCF-7
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Cytotoxins); 0 (Estranes); 0 (Hydrocarbons, Iodinated); 789U1901C5 (Copper)
[Em] Mês de entrada:1601
[Cu] Atualização por classe:150429
[Lr] Data última revisão:
150429
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150304
[St] Status:MEDLINE


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[PMID]:24455864
[Au] Autor:Andriushina VA; Iaderets VV; Stytsenko TS; Druzhinina AV; Voishvillo NE
[Ti] Título:[Effect of the steroid molecule structure on the direction of its hydroxylation by the fungus Curvularia lunata].
[So] Source:Prikl Biokhim Mikrobiol;49(4):382-90, 2013 Jul-Aug.
[Is] ISSN:0555-1099
[Cp] País de publicação:Russia (Federation)
[La] Idioma:rus
[Ab] Resumo:The main and side products of hydroxylation by the C. lunata VKPM F-981 mycelium of fourteen delta(4)-3-ketosteroids of the estrane, androstane, and pregnane series and six of their delta(5)-3beta-hydroxy analogues were identified by H1 PMR spectroscopy and comparison with standard samples. The obtained experimental data are considered in terms of the triangular model of the enzyme-substrate interaction. The dependence of the direction of hydroxylation of steroid molecules and the orientation of hydroxy groups on the structure of the initial substrate was revealed.
[Mh] Termos MeSH primário: Androstanos/metabolismo
Estranos/metabolismo
Proteínas Fúngicas/metabolismo
Cetosteroides/metabolismo
Micélio/metabolismo
Pregnanos/metabolismo
Saccharomycetales/metabolismo
[Mh] Termos MeSH secundário: Cromatografia Líquida
Espectroscopia de Ressonância de Spin Eletrônica
Hidroxilação
Estrutura Molecular
Padrões de Referência
Especificidade por Substrato
[Pt] Tipo de publicação:ENGLISH ABSTRACT; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Androstanes); 0 (Estranes); 0 (Fungal Proteins); 0 (Ketosteroids); 0 (Pregnanes)
[Em] Mês de entrada:1402
[Cu] Atualização por classe:140124
[Lr] Data última revisão:
140124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140125
[St] Status:MEDLINE


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[PMID]:23495256
[Au] Autor:Li J; Li Y; Zhang W; Chen Z; Fan G
[Ad] Endereço:Department of Pharmaceutical Analysis, School of Pharmacy, Second Military Medical University, Shanghai, P.R. China.
[Ti] Título:Glucose-ß-CD interaction assisted ACN field-amplified sample stacking in CZE for determination of trace amlodipine in beagle dog plasma.
[So] Source:J Sep Sci;36(11):1817-25, 2013 Jun.
[Is] ISSN:1615-9314
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:A simple, sensitive and low-cost method using CE coupled with glucose-ß-CD interaction assisted ACN stacking technique has been developed for quantification of trace amlodipine in dog plasma. The plasma samples were extracted with methyl tert-butyl ether. The separation was performed at 25°C in a 31.2 cm × 75 µm fused-silica capillary with an applied voltage of 15 kV. The BGE was composed of 6.25 mM borate/25 mM phosphate (pH 2.5) and 5 mg/mL glucose-ß-CD. The detection wavelength was 200 nm. Because CD could diminish the interaction between drugs and matrix, and derivation groups of CD play an important role in separation performance, the effects of ß-CD, and its derivatives on the separation were studied at several concentrations (0, 2.5, 5.0, 10.0 mg/mL). In this study, organic solvent field-amplified sample stacking technique in combination with glucose-ß-CD enhanced the sensitivity about 60-70 folds and glucose-ß-CD could effectively improve the peak shape. All the validation data, such as accuracy, precision extraction recovery, and stability, were within the required limits. The calibration curve was linear for amlodipine from 1 to 200 ng/mL. The method developed was successfully applied to the pharmacokinetic studies of amlodipine besylate in beagle dogs.
[Mh] Termos MeSH primário: Anlodipino/sangue
Anti-Hipertensivos/sangue
Eletroforese Capilar/métodos
[Mh] Termos MeSH secundário: Animais
Cães
Eletroforese Capilar/instrumentação
Estranos/química
Glucose/química
Nitrilos/química
[Pt] Tipo de publicação:EVALUATION STUDIES; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antihypertensive Agents); 0 (Estranes); 0 (Nitriles); 151774-83-3 (3-hydroxy-5-estrane-17-carbonitrile); 1J444QC288 (Amlodipine); IY9XDZ35W2 (Glucose)
[Em] Mês de entrada:1312
[Cu] Atualização por classe:130605
[Lr] Data última revisão:
130605
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130316
[St] Status:MEDLINE
[do] DOI:10.1002/jssc.201201044


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[PMID]:23378128
[Au] Autor:Matsuda T; Yamashita K; Maeda H; Hashimoto M; Tsukagoshi K
[Ad] Endereço:Department of Chemical Engineering and Materials Science, Doshisha University, Kyotanabe, Japan.
[Ti] Título:Michrochip chromatography using an open-tubular microchannel and a ternary water-ACN-ethyl acetate mixture carrier solution.
[So] Source:J Sep Sci;36(5):965-70, 2013 Mar.
[Is] ISSN:1615-9314
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:A capillary chromatography system has been developed using a ternary mixed-solvents solution, i.e. water-hydrophilic/hydrophobic organic solvent mixture as a carrier solution. Here, we tried to carry out the chromatographic system on a microchip incorporating the open-tubular microchannels. A model analyte solution of isoluminol isothiocyanate (ILITC) and ILITC-labeled biomolecule was injected to the double T-junction part on the microchip. The analyte solution was delivered in the separation microchannel (40 µm deep, 100 µm wide, and 22 cm long) with the ternary water-ACN-ethyl acetate mixture carrier solution (3:8:4 volume ratio, the organic solvent rich or 15:3:2 volume ratio, the water-rich). The analyte, free-ILITC and labeled BSA mixture, was separated through the microchannel, where the carrier solvents were radially distributed in the separation channel generating inner and outer phases. The outer phase acts as a pseudo-stationary phase under laminar flow conditions in the system. The ILITC and the labeled BSA were eluted and detected with chemiluminescence reaction.
[Mh] Termos MeSH primário: Cromatografia/instrumentação
Proteínas/química
[Mh] Termos MeSH secundário: Acetatos/química
Cromatografia/métodos
Estranos/química
Dispositivos Lab-On-A-Chip
Medições Luminescentes
Nitrilos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Acetates); 0 (Estranes); 0 (Nitriles); 0 (Proteins); 151774-83-3 (3-hydroxy-5-estrane-17-carbonitrile); 76845O8NMZ (ethyl acetate)
[Em] Mês de entrada:1308
[Cu] Atualização por classe:130313
[Lr] Data última revisão:
130313
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130205
[St] Status:MEDLINE
[do] DOI:10.1002/jssc.201200928


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[PMID]:21843695
[Au] Autor:Friedman J; Cremer M; Jelani QU; Huang X; Jian J; Shah S; Katz SD
[Ad] Endereço:Department of Medicine, New York University Langone Medical Center, New York, NY 10016, USA.
[Ti] Título:Oral contraceptive use, iron stores and vascular endothelial function in healthy women.
[So] Source:Contraception;84(3):285-90, 2011 Sep.
[Is] ISSN:1879-0518
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Increased iron stores are associated with greater cardiovascular risk in postmenopausal women. Oral contraceptive pill (OCP) use decreases the volume of menstrual blood loss and increases iron stores, but the link between OCP use, iron stores and cardiovascular risk in premenopausal women has not been characterized. STUDY DESIGN: We conducted a cross-sectional study of 23 healthy OCP users to determine the association between type and duration of OCP exposure, iron stores, and vascular endothelial function [flow-mediated dilation (FMD) in the brachial artery]. RESULTS: Median duration of OCP use was 45 months. FMD in the brachial artery was significantly associated with progestin type used (estranes/gonanes vs. drospirenone) and duration of OCP use (both p<.05) but not iron stores. In multivariate analysis, progestin type was the only independent predictor of FMD. CONCLUSIONS: Use of OCP containing drospirenone was independently associated with greater FMD in the brachial artery and, thus, a potentially more favorable cardiovascular risk profile, when compared with use of OCP containing estranes/gonanes.
[Mh] Termos MeSH primário: Doenças Cardiovasculares/sangue
Doenças Cardiovasculares/induzido quimicamente
Anticoncepcionais Orais/administração & dosagem
Anticoncepcionais Orais/efeitos adversos
Endotélio Vascular/efeitos dos fármacos
Ferro/sangue
[Mh] Termos MeSH secundário: Adulto
Androstenos/administração & dosagem
Androstenos/efeitos adversos
Velocidade do Fluxo Sanguíneo/efeitos dos fármacos
Artéria Braquial/diagnóstico por imagem
Artéria Braquial/efeitos dos fármacos
Doenças Cardiovasculares/patologia
Estudos Transversais
Estranos/administração & dosagem
Estranos/efeitos adversos
Feminino
Ferritinas/sangue
Gonanos/administração & dosagem
Gonanos/efeitos adversos
Seres Humanos
Modelos Lineares
Ultrassonografia
Vasodilatação/efeitos dos fármacos
Adulto Jovem
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Androstenes); 0 (Contraceptives, Oral); 0 (Estranes); 0 (Gonanes); 9007-73-2 (Ferritins); E1UOL152H7 (Iron); N295J34A25 (drospirenone)
[Em] Mês de entrada:1202
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110817
[St] Status:MEDLINE
[do] DOI:10.1016/j.contraception.2011.01.012


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[PMID]:21668005
[Au] Autor:Horváth A; Szájli Á; Kiss R; Kóti J; Mahó S; Skoda-Földes R
[Ad] Endereço:Department of Organic Chemistry, Institute of Chemistry, University of Pannonia, Post Office Box 158, H-8201 Veszprém, Hungary.
[Ti] Título:Ionic liquid-promoted Wagner-Meerwein rearrangement of 16α,17α-epoxyandrostanes and 16α,17α-epoxyestranes.
[So] Source:J Org Chem;76(15):6048-56, 2011 Aug 05.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Ionic liquids 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim](+)[PF(6)](-)) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim](+)[BF(4)](-)) were found to promote an unusual Wagner-Meerwein rearrangement of steroidal 16α,17α-epoxides leading to unnatural 13-epi-18-nor-16-one derivatives as the main products. These compounds were isolated in good to excellent yields. 16α-Hydroxy-Δ(13)-18-norsteroids, the results of the usual rearrangement, were obtained as minor components of the reaction mixtures. The ionic liquid [bmim](+)[PF(6)](-) was shown to induce C-ring aromatization of 16α,17α-epoxyestranes due to the formation of HF, the hydrolysis product of [PF(6)](-). Increasing amounts of HF and [PO(2)F(2)](-) were detected by (19)F and (31)P NMR when the ionic liquid was reused. The structures of the steroidal products, 16-oxo-18-nor-13α-steroid derivatives, 16α-hydroxy-Δ(13)-18-norsteroids, and C-aromatic compounds were determined by two-dimensional NMR techniques and high-resolution mass spectrometry (HRMS). The ionic liquids were recirculated efficiently.
[Mh] Termos MeSH primário: Androstanóis/química
Estranos/química
Imidazóis/química
Líquidos Iônicos/química
[Mh] Termos MeSH secundário: Estrutura Molecular
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (1-butyl-3-methylimidazolium hexafluorophosphate); 0 (1-butyl-3-methylimidazolium tetrafluoroborate); 0 (Androstanols); 0 (Estranes); 0 (Imidazoles); 0 (Ionic Liquids)
[Em] Mês de entrada:1201
[Cu] Atualização por classe:110729
[Lr] Data última revisão:
110729
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110615
[St] Status:MEDLINE
[do] DOI:10.1021/jo2006285


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[PMID]:21621615
[Au] Autor:Dervilly-Pinel G; Rambaud L; Sitthisack P; Monteau F; Hewitt SA; Kennedy DG; Le Bizec B
[Ad] Endereço:École nationale vétérinaire, agroalimentaire et de l'alimentation Nantes-Atlantique, Laboratoire d'Étude des Résidus et Contaminants dans les Aliments (LABERCA), Atlanpole - La Chantrerie, Nantes, France. gaud.pinel@oniris-nantes.fr
[Ti] Título:5α-Estrane-3ß,17ß-diol and 5ß-estrane-3α,17ß-diol: definitive screening biomarkers to sign nandrolone abuse in cattle?
[So] Source:J Steroid Biochem Mol Biol;126(3-5):65-71, 2011 Sep.
[Is] ISSN:1879-1220
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:17ß-Nandrolone (17ß-NT) is one of the most frequently misused anabolic steroids in meat producing animals. As a result of its extensive metabolism combined with the possibility of interferences with other endogenous compounds, detection of its illegal use often turns out to be a difficult issue. In recent years, proving the illegal administration of 17ß-NT became even more challenging since the presence of endogenous presence of 17ß-NT or some of its metabolite in different species was demonstrated. In bovines, 17α-NT can occur naturally in the urine of pregnant cows and recent findings reported that both forms can be detected in injured animals. Because efficient control must both take into account metabolic patterns and associated kinetics of elimination, the purpose of the present study was to investigate further some estranediols (5α-estrane-3ß,17ß-diol (abb), 5ß-estrane-3α,17ß-diol (bab), 5α-estrane-3ß,17α-diol (aba), 5α-estrane-3α,17ß-diol (aab) and 5ß-estrane-3α,17α-diol (baa)) as particular metabolites of 17ß-NT on a large number of injured (n=65) or pregnant (n=40) bovines. Whereas the metabolites abb, bab, aba and baa have previously been detected in urine up to several days after 17ß-NT administration, the present study showed that some of the isomers abb (5α-estrane-3ß,17ß-diol) and bab (5ß-estrane-3α,17ß-diol) could not be detected in injured or pregnant animals, even at very low levels. This result may open a new way for the screening of anabolic steroid administration considering these 2 estranediols as biomarkers to indicate nandrolone abuse in cattle.
[Mh] Termos MeSH primário: Biomarcadores/análise
Estranos/análise
Nandrolona
Prenhez
Detecção do Abuso de Substâncias/métodos
Transtornos Relacionados ao Uso de Substâncias/diagnóstico
[Mh] Termos MeSH secundário: Anabolizantes/metabolismo
Anabolizantes/farmacologia
Animais
Biomarcadores/sangue
Bovinos
Doenças dos Bovinos/sangue
Doenças dos Bovinos/diagnóstico
Doenças dos Bovinos/metabolismo
Estranos/sangue
Feminino
Cromatografia Gasosa-Espectrometria de Massas
Isomerismo
Nandrolona/metabolismo
Nandrolona/farmacologia
Gravidez/sangue
Gravidez/metabolismo
Prenhez/sangue
Prenhez/metabolismo
Transtornos Relacionados ao Uso de Substâncias/sangue
Transtornos Relacionados ao Uso de Substâncias/metabolismo
Ferimentos e Lesões/sangue
Ferimentos e Lesões/metabolismo
Ferimentos e Lesões/veterinária
[Pt] Tipo de publicação:EVALUATION STUDIES; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anabolic Agents); 0 (Biomarkers); 0 (Estranes); 517-01-1 (estrane-3,17-diol); 6PG9VR430D (Nandrolone)
[Em] Mês de entrada:1109
[Cu] Atualização por classe:151119
[Lr] Data última revisão:
151119
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110531
[St] Status:MEDLINE
[do] DOI:10.1016/j.jsbmb.2011.05.005


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[PMID]:21236283
[Au] Autor:de la Torre X; Colamonici C; Curcio D; Molaioni F; Pizzardi M; Botrè F
[Ad] Endereço:Laboratorio Antidoping, Federazione Medico Sportiva Italiana, Largo Giulio Onesti 1, 00197 Rome, Italy. xavier.delatorre@gmail.com
[Ti] Título:A simplified procedure for GC/C/IRMS analysis of underivatized 19-norandrosterone in urine following HPLC purification.
[So] Source:Steroids;76(5):471-7, 2011 Apr.
[Is] ISSN:1878-5867
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Nandrolone and/or its precursors are included in the World Anti-doping Agency (WADA) list of forbidden substances and methods and as such their use is banned in sport. 19-Norandrosterone (19-NA) the main metabolite of these compounds can also be produced endogenously. The need to establish the origin of 19-NA in human urine samples obliges the antidoping laboratories to use isotope ratio mass spectrometry (IRMS) coupled to gas chromatography (GC/C/IRMS). In this work a simple liquid chromatographic method without any additional derivatization step is proposed, allowing to drastically simplify the urine pretreatment procedure, leading to extracts free of interferences permitting precise and accurate IRMS analysis. The purity of the extracts was verified by parallel analysis by gas chromatography coupled to mass spectrometry with GC conditions identical to those of the GC/C/IRMS assay. The method has been validated according to ISO17025 requirements (within assay precision of ±0.3‰ and between assay precision of ±0.4‰). The method has been tested with samples obtained after the administration of synthetic 19-norandrostenediol and samples collected during pregnancy where 19-NA is known to be produced endogenously. Twelve drugs and synthetic standards able to produce through metabolism 19-NA have shown to present δ(13)C values around -29‰ being quite homogeneous (-28.8±1.5; mean±standard deviation) while endogenously produced 19-NA has shown values comparable to other endogenous produced steroids in the range -21 to -24‰ as already reported. The efficacy of the method was tested on real samples from routine antidoping analyses.
[Mh] Termos MeSH primário: Estranos/urina
Cromatografia Gasosa-Espectrometria de Massas/métodos
Detecção do Abuso de Substâncias/métodos
[Mh] Termos MeSH secundário: Cromatografia Líquida de Alta Pressão
Doping nos Esportes/prevenção & controle
Estranos/isolamento & purificação
Feminino
Seres Humanos
Masculino
Nandrolona/análogos & derivados
Gravidez
Reprodutibilidade dos Testes
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; VALIDATION STUDIES
[Nm] Nome de substância:
0 (Estranes); 5W4XKU708V (19-norandrosterone); 6PG9VR430D (Nandrolone)
[Em] Mês de entrada:1107
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110118
[St] Status:MEDLINE
[do] DOI:10.1016/j.steroids.2011.01.001



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