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1.
Exp Clin Psychopharmacol ; 26(4): 329-334, 2018 08.
Artigo em Inglês | MEDLINE | ID: mdl-29878800

RESUMO

Addiction is characterized as a chronic debilitating disease. One devastating feature of addiction is the susceptibility of relapse (40-60%) after stretches of abstinence. One theory that may account for relapse suggests that drug cues (e.g., paraphernalia) may increase stress hormones, and this may prompt relapse. Repeatedly pairing a neutral cue with a reward is commonly utilized to measure what subjects learn about a cue that is predictive of reward. Research has shown that animals that attend to a cue more than to the reward (sign trackers) may be more vulnerable to drug addiction. Additionally, research has shown that sign tracking is associated with an increase in corticosterone, a primary stress hormone. PT150 is a novel glucocorticoid receptor antagonist that moderates the release of corticosterone. In the current experiment, it was hypothesized that subjects given repeated administration of PT150 would reduce sign tracking compared to subjects given placebo. Time spent (in seconds) near a cue that predicts reward (conditional stimulus) served as a measure of sign tracking, and PT150 or placebo was administered following sign tracking. An independent-samples t test revealed that subjects that received PT150 had reduced time spent near the conditioned stimulus compared to controls. Given the devastating effects of drug addiction, identification of a potential pharmacological intervention in the reduction of relapse would be of great value. Therefore, future research is needed to validate the use of PT150 in reducing behaviors associated with drug addiction. (PsycINFO Database Record


Assuntos
Comportamento Aditivo/tratamento farmacológico , Sinais (Psicologia) , Norpregnanos/farmacologia , Receptores de Glucocorticoides/antagonistas & inibidores , Receptores de Glucocorticoides/fisiologia , Recompensa , Animais , Comportamento Aditivo/psicologia , Condicionamento Clássico/efeitos dos fármacos , Condicionamento Clássico/fisiologia , Coturnix , Masculino , Motivação/efeitos dos fármacos , Motivação/fisiologia , Norpregnanos/química , Norpregnanos/uso terapêutico , Ratos Sprague-Dawley
2.
Gynecol Endocrinol ; 31(5): 414-8, 2015 May.
Artigo em Inglês | MEDLINE | ID: mdl-25856298

RESUMO

The effects of the postmenopausal replacement steroid tibolone and its 3α-, 3ß-OH and Δ-4 tibolone metabolites were evaluated on progesterone receptor-mediated classic decidualization markers insulin-like growth factor binding protein-1 (IGFBP-1) and prolactin expression in human endometrial stromal cells (HESCs). Supernatants of conditioned medium or erxtracted RNA from experimental cell incubations of confluent HESCs were subjected to ELISAs, Western blot analysis and RT/PCR, and results were statisically assesed. Over 21 days, specific ELISAs observed linear increases in secreted IGFBP-1 and prolactin levels elicited by tibolone and its metabolites. Cultured HESCs were refractory to E2 and dexamethasone, whereas tibolone and each metabolite exceeded medroxyprogesterone acetate in significantly elevating IGFBP-1 and prolactin output. Anti-progestins eliminated IGFBP-1 and prolactin induction by tibolone and its metabolites. Immunoblotting and RT/PCR confirmed ELISA results. These observations of IGFBP-1 and prolactin expression: (a) indicate the relevance of cultured HESCs in evaluating the chronic effects of tibolone administration to women; (b) are consistent with PR-mediated endometrial atrophy and protection against endometrial bleeding despite the persistence of circulating ER-binding, but not PR-binding metabolites following tibolone administration to women.


Assuntos
Endométrio/efeitos dos fármacos , Moduladores de Receptor Estrogênico/farmacologia , Proteína 1 de Ligação a Fator de Crescimento Semelhante à Insulina/efeitos dos fármacos , Norpregnenos/farmacologia , Prolactina/efeitos dos fármacos , RNA Mensageiro/efeitos dos fármacos , Células Estromais/efeitos dos fármacos , Western Blotting , Anticoncepcionais Femininos/farmacologia , Dexametasona/farmacologia , Endométrio/citologia , Endométrio/metabolismo , Ensaio de Imunoadsorção Enzimática , Estradiol/farmacologia , Estrenos/farmacologia , Estrogênios/farmacologia , Feminino , Furanos/farmacologia , Glucocorticoides/farmacologia , Antagonistas de Hormônios/farmacologia , Humanos , Proteína 1 de Ligação a Fator de Crescimento Semelhante à Insulina/genética , Proteína 1 de Ligação a Fator de Crescimento Semelhante à Insulina/metabolismo , Acetato de Medroxiprogesterona/farmacologia , Mifepristona/farmacologia , Norpregnanos/farmacologia , Prolactina/genética , Prolactina/metabolismo , RNA Mensageiro/metabolismo , Reação em Cadeia da Polimerase em Tempo Real , Células Estromais/metabolismo
3.
Mol Cell Endocrinol ; 382(2): 899-908, 2014 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-24239616

RESUMO

Medroxyprogesterone acetate (MPA) has widely been used in hormone replacement therapy (HRT), and is associated with an increased risk of breast cancer, possibly due to disruption of androgen receptor (AR) signaling. In contrast, the synthetic HRT Tibolone does not increase breast density, and is rapidly metabolized to estrogenic 3α-OH-tibolone and 3ß-OH-tibolone, and a delta-4 isomer (Δ(4)-TIB) that has both androgenic and progestagenic properties. Here, we show that 5α-dihydrotestosterone (DHT) and Δ(4)-TIB, but not MPA, stabilize AR protein levels, initiate specific AR intramolecular interactions critical for AR transcriptional regulation, and increase proliferation of AR positive MDA-MB-453 breast cancer cells. Structural modeling and molecular dynamic simulation indicate that Δ(4)-TIB induces a more stable AR structure than does DHT, and MPA a less stable one. Microarray expression analyses confirms that the molecular actions of Δ(4)-TIB more closely resembles DHT in breast cancer cells than either ligand does to MPA.


Assuntos
Androgênios/farmacologia , Di-Hidrotestosterona/farmacologia , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Proteínas de Neoplasias/genética , Norpregnenos/farmacologia , Receptores Androgênicos/genética , Androgênios/química , Androgênios/metabolismo , Biotransformação , Linhagem Celular Tumoral , Di-Hidrotestosterona/química , Di-Hidrotestosterona/metabolismo , Feminino , Perfilação da Expressão Gênica , Humanos , Acetato de Medroxiprogesterona/química , Acetato de Medroxiprogesterona/farmacologia , Simulação de Dinâmica Molecular , Proteínas de Neoplasias/metabolismo , Norpregnanos/metabolismo , Norpregnenos/química , Norpregnenos/metabolismo , Análise de Sequência com Séries de Oligonucleotídeos , Receptores Androgênicos/metabolismo , Relação Estrutura-Atividade
4.
Menopause ; 17(6): 1122-7, 2010.
Artigo em Inglês | MEDLINE | ID: mdl-20613675

RESUMO

OBJECTIVE: Although the route of estrogen administration is known to be an important determinant of the thrombotic risk among postmenopausal women using hormone therapy, recent data have shown that norpregnane derivatives but not micronized progesterone increase venous thromboembolism risk among transdermal estrogens users. However, the differential effects of progesterone and norpregnanes on hemostasis have not yet been investigated. METHODS: We set up a cross-sectional study among healthy postmenopausal women aged 45 to 70 years. The impact of activated protein C (APC) on endogenous thrombin potential was investigated in the plasma samples of 108 women who did not use any hormone therapy (n = 40) or who were treated with transdermal estrogens combined with micronized progesterone (n = 30) or norpregnane derivatives (n = 38). RESULTS: After exclusion of women with factor V Leiden and/or G20210A prothrombin gene mutations, there was no significant change in APC sensitivity among women who used transdermal estrogens combined with micronized progesterone compared with nonusers. Women using transdermal estrogens combined with norpregnanes were less sensitive to APC than were nonusers (P = 0.003) or users of transdermal estrogens combined with micronized progesterone (P = 0.004). In addition, prothrombin fragment 1 + 2 concentration was higher in users of transdermal estrogens plus norpregnanes than in nonusers (P = 0.004). Other hemostatic parameters did not vary significantly across the different subgroups. CONCLUSIONS: Transdermal estrogens combined with norpregnanes may induce APC resistance and activate blood coagulation. These results provide a biological support to epidemiological data regarding the potential thrombogenic effects of norpregnanes. However, these findings need to be confirmed in a randomized trial.


Assuntos
Resistência à Proteína C Ativada/etiologia , Terapia de Reposição de Estrogênios/efeitos adversos , Estrogênios/administração & dosagem , Hemostasia/efeitos dos fármacos , Norpregnanos/administração & dosagem , Pós-Menopausa/sangue , Progestinas/administração & dosagem , Resistência à Proteína C Ativada/sangue , Administração Cutânea , Idoso , Estudos Transversais , Quimioterapia Combinada , Estrogênios/efeitos adversos , Feminino , Humanos , Modelos Lineares , Pessoa de Meia-Idade , Norpregnanos/efeitos adversos , Fragmentos de Peptídeos/sangue , Fragmentos de Peptídeos/efeitos dos fármacos , Progestinas/efeitos adversos , Protrombina/efeitos dos fármacos , Trombina/biossíntese , Trombina/efeitos dos fármacos
5.
J Steroid Biochem Mol Biol ; 116(1-2): 8-14, 2009 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-19464167

RESUMO

This work was undertaken (i) to study deeply the estrogen, androgen and progestative activities of tibolone and its metabolites (ii) to determine whether tibolone and its metabolites present glucocorticoid or mineralocorticoid activity. For this purpose, we used human cell lines bearing a luciferase gene with a responsive element under the control of human estrogen receptor alpha (ERalpha) or estrogen receptor beta (ERbeta) or androgen receptor (AR) or chimeric Gal4 fusion with progesterone receptor (PR), glucocorticoid receptor (GR) or mineralocorticoid receptor (MR). The major tibolone metabolites, the two hydroxymetabolites, bind and activate ER with a preference for ERalpha. Tibolone and the Delta(4)-tibolone are agonists for AR and PR and surprisingly 3alpha- and 3beta-OH-tibolone are antagonists for them. Moreover we showed for the first time that tibolone and its primary metabolites are GR and MR antagonists with a stronger affinity for MR than for GR. In conclusion, tibolone by these actions on different receptors and by this capacity to transform in different metabolites, has more complex effects than initially supposed.


Assuntos
Moduladores de Receptor Estrogênico/farmacologia , Norpregnenos/farmacologia , Receptores de Esteroides/metabolismo , Androgênios , Linhagem Celular , Moduladores de Receptor Estrogênico/metabolismo , Receptor alfa de Estrogênio/genética , Receptor alfa de Estrogênio/metabolismo , Receptor beta de Estrogênio/genética , Receptor beta de Estrogênio/metabolismo , Genes Reporter , Humanos , Luciferases/genética , Luciferases/metabolismo , Norpregnanos/metabolismo , Norpregnenos/metabolismo , Receptores Androgênicos/metabolismo , Receptores de Progesterona/agonistas , Receptores de Progesterona/metabolismo , Receptores de Esteroides/genética
6.
Acta Crystallogr C ; 65(Pt 5): o214-6, 2009 May.
Artigo em Inglês | MEDLINE | ID: mdl-19407419

RESUMO

In the title compound, C(23)H(34)O(4), which is an intermediate in the synthesis of pregnane derivatives with a modified skeleton that show potent abortion-inducing activity, the conformation of ring B is close to half-chair due to the presence of both the C=C double bond and the axial 5beta-methyl group. Rings A and C have conformations close to chair, while ring D has a twisted conformation around the bridgehead C-C bond. Molecules are hydrogen bonded via the hydroxyl and acetoxy groups into infinite chains. Quantum-mechanical ab initio Roothan Hartree-Fock calculations show that crystal packing might be responsible for the low values of the angles between rings A and B, and between ring A and rings C and D, as well as for a different steric position of the methyl ketone side chain compared to the geometry of the free molecule.


Assuntos
Abortivos Esteroides/química , Cristalografia por Raios X , Norpregnanos/química , Pregnanos/química , Abortivos Esteroides/síntese química , Feminino , Humanos , Ligação de Hidrogênio , Conformação Molecular , Norpregnanos/síntese química , Gravidez , Pregnanos/síntese química , Teoria Quântica
8.
Menopause ; 15(2): 386-7, 2008.
Artigo em Inglês | MEDLINE | ID: mdl-18000470

RESUMO

In an earlier study, we focused on the vasoactive effect of 3alpha-OH-tibolone on spontaneously constricted isolatedfemale rat gracilis muscle arterioles. Vasodilator effects (from 10 to 10 M) of 3alpha-OH-tibolone were similar to those of 17beta-estradiol. It was reported that 3beta-OH-tibolone like estradiol altered GABAB activation in neurons through a membrane estrogen receptor, whereas the 3alpha-OH metabolite did not. We therefore hypothesized that the 3beta-OH metabolite may also have a vasodilating effect in our isolated arteriole model. The results indicate that 3beta-OH-tibolone induces a vasodilator effect in small arterioles that is comparable with that of 3alpha-OH-tibolone at the same concentration. This is intriguing because the binding affinity of 3alpha-OH-tibolone to the estrogen receptor is almost twice that of 3beta-OH-tibolone. Other mechanisms may play a role.


Assuntos
Arteríolas/efeitos dos fármacos , Endotélio Vascular/efeitos dos fármacos , Moduladores de Receptor Estrogênico/farmacologia , Norpregnanos/farmacologia , Norpregnenos/farmacologia , Vasodilatação/efeitos dos fármacos , Animais , Relação Dose-Resposta a Droga , Feminino , Músculo Esquelético/irrigação sanguínea , Ratos , Ratos Wistar
10.
Nat Prod Res ; 20(12): 1074-81, 2006 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-17201044

RESUMO

The microbial transformation of levonorgestrel (1) by Cunningham elegans resulted in the formation of five hydroxylated metabolites, 13-ethyl-10beta, 17beta-dihydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one(2), 13-ethyl-6beta,17beta-dihydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one (3) 13-ethyl 6beta, 10beta, 17beta-trihydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one (4) 13-ethyl-15alpha-17beta-dihydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one (5) and 13-ethyl-11alpha, 17beta-dihydroxy-18,19-dinor-17alpha-pregn-4en-20-yn-3-one. The fermentation of one with Rhizopus stolonifer, Fusarium lini and Curvularia lunata afforded compound 2 as a major metabolise. These metabolites were structurally characterized on the basis of spectroScopic techniques. Metabolite 6 was identified as a new compound. Compounds 2 2 ad 5 displayed inhibitory activity against the acetylcholinesterase ( AChE, EC. 3.1.1.7) with IC50 values of 79.2 and 24.5 microM, respectively. The metabolites 2 and 5 also showed inhibitory activity against the butyryLcholinesterase ( BChE, E.C 3.1.1.8) with IC50 values ranging between 9.4 and 309.8 microM.


Assuntos
Inibidores da Colinesterase/metabolismo , Cunninghamella/metabolismo , Levanogestrel/química , Levanogestrel/metabolismo , Norpregnanos/química , Norpregnanos/metabolismo , Butirilcolinesterase/metabolismo , Fermentação , Hidroxilação , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Análise Espectral
11.
Fresenius J Anal Chem ; 368(4): 384-8, 2000 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-11227508

RESUMO

delta4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi* electronic transition (270-350 nm). With hydroxylamine hydrochloride, delta4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of delta4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, testosterone phenylpropionate, nortestosterone phenylpropionate) varies linearly with the concentration in the interval 6 x 10(-6)-3 x 10(-3) mol/L. The method can be well applied to determination of delta4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10% impurity can be measured.


Assuntos
Cetosteroides/análise , Oximas/análise , Oximas/síntese química , Dicroísmo Circular , Contaminação de Medicamentos , Hormônios Esteroides Gonadais/análise , Hormônios Esteroides Gonadais/química , Hormônios Esteroides Gonadais/normas , Cetosteroides/química , Cetosteroides/normas , Norpregnanos/análise , Norpregnanos/química , Norpregnanos/normas , Oximas/química , Testosterona/análise , Testosterona/química , Testosterona/normas
12.
J Nat Prod ; 62(2): 318-20, 1999 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-10075773

RESUMO

Two new norpregnane glycosides, 19-norpregna-1,3,5(10), 20-tetraen-3-O-alpha-fucopyranoside (3) and 19-norpregna-1,3,5(10), 20-tetraen-3-O-beta-arabinopyranoside (4), were isolated from the soft coral Scleronephthya pallida, along with two known steroids, pregna-1,20-dien-3-one (1) and 19-norpregna-1,3,5(10), 20-tetraen-3-ol (2). 19-Norpregna-1,3,5(10), 20-tetraen-3-O-alpha-fucopyranoside (3) exhibits moderate antimalarial and cytotoxic activities. The chemical structures of 1-4 were elucidated from spectroscopic data.


Assuntos
Antimaláricos/isolamento & purificação , Cnidários/química , Glicosídeos/isolamento & purificação , Norpregnanos/isolamento & purificação , Animais , Antimaláricos/química , Antimaláricos/farmacologia , Sequência de Carboidratos , Glicosídeos/química , Glicosídeos/farmacologia , Norpregnanos/química , Norpregnanos/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Análise Espectral
13.
J Steroid Biochem Mol Biol ; 55(1): 77-84, 1995 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-7577723

RESUMO

Estrogen receptors of human endometrial cancer Ishikawa cells were found to be present in moderate amounts (160-200 fmol/mg protein), and to specifically bind moxestrol (R2858) with a very high affinity characterized by a Kd around 60 pM, when measured under equilibrium conditions. The binding specificity respected a decreasing order as follows: estradiol (E2: 100%) > 4-hydroxy-tamoxifen (4OHTAM: 52.7%) > estriol (E3: 5.7%) > estrone (E1: 2.1%) > TAM (0.2%). The induction of alkaline phosphatase activity (APase) used as an estrogen-specific response, confirmed the intrinsic estrogenicity of progestins derived from 19-nor-testosterone (19NT): norethindrone (NOR), norethynodrel and levonorgestrel, at concentrations ranging from 10(-8) to 10(-6) M. The effect of NOR was partially blocked by the antiestrogen 4OHTAM, which was also partially agonistic in this model, but neither by the antiprogestin mifepristone (RU486) nor by the aromatase inhibitor aminoglutethimide. A simulatory effect was also detected at 10(-7) or 10(-6) M with ethindrone, the testosterone- (T) derived progestin homologous to NOR, and with both androgenic parent-compounds, i.e. T and 19NT themselves. In contrast, progesterone (P) derivatives like medroxyprogesterone acetate (MPA) and chlormadinone acetate (CMA) remained totally inactive, as well as 19-nor-progesterone (19NP) itself or its progestagenic derivatives: ORG 2058 and nomegestrol acetate (NOM). Structure-activity relationships deduced from these studies suggest that it is not the absence of the 19-methyl group which can account for the estrogenic potential of the so-called "19-norprogestins", but rather their steroid structure derived from T in a broad sense (including the 19NT derivatives), as opposed to the non-estrogenic therapeutic progestins derived from P like MPA or CMA, or from 19NP like NOM.


Assuntos
Endométrio/efeitos dos fármacos , Estrogênios/farmacologia , Norpregnanos/farmacologia , Progesterona/análogos & derivados , Progestinas/farmacologia , Testosterona/análogos & derivados , Adenocarcinoma , Fosfatase Alcalina/biossíntese , Aminoglutetimida/farmacologia , Inibidores da Aromatase , Ligação Competitiva , Citosol/metabolismo , Neoplasias do Endométrio , Endométrio/citologia , Endométrio/metabolismo , Indução Enzimática , Inibidores Enzimáticos/farmacologia , Congêneres do Estradiol/metabolismo , Estrogênios/metabolismo , Etinilestradiol/análogos & derivados , Etinilestradiol/metabolismo , Feminino , Humanos , Nandrolona/análogos & derivados , Nandrolona/farmacologia , Norprogesteronas/farmacologia , Pregnanos/farmacologia , Receptores Estrogênicos/metabolismo , Tamoxifeno/farmacologia , Células Tumorais Cultivadas
15.
Fortschr Med ; 95(29): 1827-32, 1977 Aug 04.
Artigo em Alemão | MEDLINE | ID: mdl-885464

RESUMO

The contraceptive effect of continuous treatment with low dose progestogens (minipill) has been attributed mainly to alterations of the cervical mucus and the endometrium. This study was undertaken to investigate the effect of low dose progestogens on hypothalamic-pituitary-ovarian function. Plasma concentrations of follicle stimulating hormone (FSH), luteininzing hormone (LH), estradiol-17 beta (E-2) and Progesterone were measured daily during apparently ovulatory menstrual cycles and during treatment cycles with different low dose progestogens. From the results obtained it was concluded that the minipill has a clear-cut effect on the LH/FSH peak at midcycle and on corpus luteum function. A cyclic secretion of E-2 is maintained in the majority of cases. In a few treatment cycles however, follicular maturation was suppressed as indicated by low E-2 concentrations. It was concluded that the minipill exerts a profound effect at the central and ovarian level which contributes to its satisfactory contraceptive efficacy.


Assuntos
Sistema Hipotálamo-Hipofisário/efeitos dos fármacos , Norpregnanos/farmacologia , Ovário/efeitos dos fármacos , Adulto , Feminino , Humanos , Linestrenol/farmacologia , Noretindrona/farmacologia , Norgestrel/farmacologia
18.
Acta Endocrinol (Copenh) ; 78(4): 791-800, 1975 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-1173966

RESUMO

Some aspects of the metabolism of lynestrenol acetate, an orally active contraceptive compound, were studied in female rats. Lynestrenol acetate is stable in gastric and intestinal juice in vitro. After intravenous administration of lynestrenol acetate and lynestrenol with a -14C label in the nucleus approximately 40% of the administered radioactivity was excreted in the bile within 90 min. After administration of lynestrenol acetate labelled in the ester group, 6% of the radioactivity was found in the bile. This means that the greater part of the lynestrenol acetate had lost its acetate group during the process of metabolism. There was an important difference between the autoradiograms of the thin layer patterns of post-hydrolysis extracts after administration of [4-14C]lynestrenol acetate and those after administration of [1'-14C]lynestrenol acetate and [4-14C]lynestrenol: the major metabolite of [4-14C]lynestrenol acetate did not appear on the autoradiograms of [1'--14C]lynestrenol acetate and [4-14C]lynestrenol. This indicates that lynestrenol acetate was altered in the nucleus in the presence of the acetate group. The acetate group itself was removed, either when the alterations took place, or after it had been completed. The results of IR, NMR and mass spectrometry analysis indicate the introduction of a 15alpha hydroxyl group. Results of gas-liquid chromatography and thin layer chromatography indicate that a second important metabolic is 19-nor-17alpha-pregn-20-yne-3alpha, 17beta-diol. The main conclusions are: 1. A part of the lynestrenol acetate is metabolized and excreted in the bile, the acetate group still being present. 2. Lynestrenol acetate is to some extent metabolized via another pathway than lynestrenol. This indicates that esterification of a steroid can lead to deviation from the metabolic pathway of the free original steroid.


Assuntos
Bile/metabolismo , Linestrenol/metabolismo , Acetatos/administração & dosagem , Acetatos/sangue , Animais , Feminino , Hidrólise , Hidroxiesteroides/biossíntese , Linestrenol/administração & dosagem , Linestrenol/sangue , Espectrometria de Massas , Norpregnanos/biossíntese , Ratos
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