Unsaturated androstane derivatives which are substituted with two hydroxy groups in any position in the ring system.

Emergent immunoregulatory properties of combined glucocorticoid and anti-glucocorticoid steroids in a model of tuberculosis. (1/29)

In Balb/c mice with pulmonary tuberculosis, there is a switch from a protective Th1-dominated cytokine profile to a non-protective profile with a Th2 component. This switch occurs while the adrenals are undergoing marked hyperplasia. Treatment with the anti-glucocorticoid hormones dehydroepiandrosterone or 3 beta, 17 beta-androstenediol, during the period of adrenal hyperplasia, maintains Th1 dominance and is protective. We investigated the effects of these hormones as therapeutic agents by administering them from day 60, when the switch to the non-protective cytokine profile was already well established. Given at this time (day 60), doses that were protective when given early (from day 0) were rapidly fatal. A physiological dose of the glucocorticoid corticosterone was also rapidly fatal. However when the corticosterone and the anti-glucocorticoid (AED or DHEA) were co-administered, there was protection, with restoration of a Th1-dominated cytokine profile, enhanced DTH responses, and enhanced expression of IL-1 alpha and TNF alpha. Therefore this combination of steroids has an emergent property that is quite unlike that of either type of steroid given alone. It may be possible to exploit the ant-inflammatory properties of glucocorticoids while preserving a Th1 bias, by combining glucocorticoids with DHEA or suitable metabolites.  (+info)

Over-the-counter anabolic steroids 4-androsten-3,17-dione; 4-androsten-3beta,17beta-diol; and 19-nor-4-androsten-3,17-dione: excretion studies in men. (2/29)

Since the appearance of 4-androsten-3,17-dione (I) as a nutritional supplement in early 1997, we have frequently observed a characteristic deterioration of endogenous steroid profiles in athletes' urine in routine anabolic steroid testing in which concentrations of major endogenous urinary steroids and testosterone exceed normal. Human excretion studies are performed with I and newer, over-the-counter "supplements" 4-androsten-3beta,17beta-diol (II) and 19-nor-4-androsten-3,17-dione (III). Endogenous urinary steroids affected by I and II are androsterone, etiocholanolone, their hydroxylated derivatives 5alpha- and 5beta-androstan-3alpha,17beta-diols, testosterone, and epitestosterone. Their concentrations briefly increase by one to two orders of magnitude and return to normal 24 h after oral administration of I and II. The average male may test positive for testosterone because testosterone concentration rises faster than that of epitestosterone, causing the testosterone/epitestosterone (T/E) ratio to rise above the positive cutoff of 6:1. A remarkable distinction in excretion patterns was observed in eastern Asian men, for whom I and II did not affect urinary concentrations of testosterone and did not increase the T/E ratio. First-pass metabolism deactivates most of the orally administered drugs I and II, rapidly converting them into inactive androsterone and etiocholanolone. Drug II is a more effective testosterone booster because of its different metabolic pathway. After the use of III, a precursor of the potent anabolic nandrolone, high concentrations of norandrosterone and noretiocholanolone appear in urine, similar to nandrolone. These are detectable in urine for 7-10 days after a single oral dose of III (50 mg).  (+info)

Regulation and substrate specificity of a steroid sulfate-specific hydroxylase system in female rat liver microsomes. (3/29)

The sulfate-specific hydroxylase system in liver microsomes from rats has been investigated with respect to its substrate specificity. Eighteen different C18, C19, C21, and C27 steroid sulfates and the coresponding free steroids have been incubated with microsomal preparations from male and female rats. The sulfate-specific system was only present in preparations from female rats and primarily catalyzed hydroxylation in position 15beta but also in position 7beta. In contrast to this, male liver microsomes were more efficient than female liver microsomes in hydroxylating free steroids; these were hydroxylated in positions 2alpha,2beta,6alpha,6beta,7alpha,7beta,16alpha, and 18. The sulfate-specific hydroxylase system in female liver microsomes was found to have rigid requirements c concerning the structure of ring D in the substrate molecule; only 17beta-sulfates (C18 and C19 steroids) and 21-sulfates (C21 steroids) were hydroxylated. Less rigid criteria, however, exist concerning the structure of ring A. The following K-m values were determined for microsomal 15beta-hydroxylation: 5alpha-androstane-3alpha,17beta-diol disulfate, 17.2 muM; 5beta-androstane-3alpha,17beta-diol disulfate, 16muM;5alpha-androstane-3alpha,17beta-diol 17-sulfate, 26 muM; and estradiol 17-sulfate, 181 muM. Some of the regulatory mechanism controlling the activity of the sex-specific 15beta-hydroxylase system also have been studied and compared to the mechanism controlling the activities of the less specific 2alpha-, 7alpha-, and 18-hydroxylase systems active on 5alpha-[4-14C]androstane-3alpha,17beta-diol. Biliary drainage did not affect the 15beta-hydroxylase activity, whereas the 2alpha- and 7alpha-hydroxylase activities decreased..  (+info)

Metabolism of [4-14C] testosterone in the rat uterus in vitro. (4/29)

In view of the uterine action of androgens we have investigated in vitro the metabolism of [4-14C]-testosterone in uterine tissue of ovariectomized rats. After purification of the extracts on Amberlite XAD-2 the metabolites have been isolated by gel. Five metabolites were isolated and identified during these incubation studies: 4-androstene 3,17-dione, 17beta-hydroxy-5alpha-androstan-3-one, 5 alpha-androstane-3alpha17beta-diol, 4-androstene-3 beta, 17beta-diol and 4-androstene-3alpha, 17beta-diol. Furthermore, two polar C19O3-metabolites and one isopolar to 5 alpha-androstane-3, 17-dione have also been detected. The metabolites were characterized by radioactive gas chromatogrphy, and determination of the relative specific activity in the eluates of Sephadex column chromatography. The identification of allylic alcohols was complemented by their oxidation to 4-androstene-3,17-dione. The present data show that activity of 17beta,3alpha- and 3beta-hydroxysteroid-oxidoreductase and 5alpha-ring-reductase are involved in the metabolism of testosterone in vitro in the rat uterus. The very low 5 alpha-reductase activity under the experimental conditions used in this work explains the formation of allylalcohols as the principal metabolites of testosterone in the rat uterus.  (+info)

Changes with age in the occurrence of C19 steroids in the testis and submaxillary gland of the boar. (5/29)

After extraction from the testes of boars of different ages, C19 steroids including 16-androstenes were determined by gas-liquid chromatography. Similarly, 16-androstenes were determined in the submaxillary glands of these boars. A high concentration of testosterone was found in the testes of 84-day-old fetuses, and this might be significant in the differentiation of male behaviour. The amount of testosterone exceeded that of androstenedione during postnatal development, and dehydroepiandrosterone and 5-androstenediol as free and sulphates were found in high concentrations particularly in postpubertal boars, suggesting that the 5-ene pathway for the synthesis of testosterone might be important. There was a change in the predominance of individual 16-androstenes in the testis during development, which closely paralleled the sequence for the biosynthesis of these compounds proposed from previous studies in vitro. Whereas the amount of 5alpha-androst-16-en-3beta-ol exceeded that of 5alpha-androst-16-en-3alpha-ol in post-pubertal testes, 5alpha-androst-16-en-3alpha-ol was predominant in the submaxillary glands at all ages. The high concentration of 16-androstenes found in the mature boar, are discussed in relation to their release as pheromones and as factors responsible for taint in boar meat.  (+info)

The occurrence of C19 steroids in testicular tissue and submaxillary glands of intersex pigs in relation to morphological characteristics. (6/29)

Five true hermaphrodite pigs and two male pseudohermaphrodite pigs were studied. A 38XX sex chromosome constitution was found in peripheral leucocytes of three true hermaphrodites and in one male pseudohermaphrodite; XX/XY mixoploidy was present in the leucocytes of the remaining male pseudohermaphrodite. The occurrence of C19 steroids, including 16-androstenes, in the testicular tissue and submaxillary gland of intersex pigs was of a similar pattern to that found previously in mature boars, and masculinization of the genital tract was related to the amount of testicular tissue present. It is postulated that in the absence of germ cells in the testicular tissue of intersex pigs the Sertoli cells may be involved in the metabolism of dehydroepiandrosterone to 5-androstenediol, a possible testosterone precursor in the pig. The high levels of 16-androstenes found in the submaxillary gland of intersex pigs indicates that these steroids are responsible for 'boar taint' in these animals. In contrast to the boar, no consistent relationship was found between the occurrence of C19 steroids and the degree of masculinization of the submaxillary gland; it is postulated that the predominantly female genetic constitution may have affected the response of the salivary gland to androgen.  (+info)

Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. (7/29)

Nandrolone is one of the synthetic anabolic steroids banned in sports and has been a popular substance abused by athletes in recent years. One of its major metabolites, 19-norandrosterone (19-NA), has been used as a determinant for drug violations in sports. Current reports regarding nandrolone-positive cases have been related to intake of some nandrolone-free nutritional supplements. The aim of this study was to learn whether if a nutritional supplement sold by over-the-counter (OTC) nutritional stores could yield the same metabolic products as that of nandrolone. If so, what is (are) the substance(s) that contributed to the nandrolone metabolites? To determine the content of an OTC nutritional supplement, a tablet was dissolved in methanol, followed by N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA)-trimethyliodosilane (TMIS) derivatization prior to gas chromatography-mass spectrometry (GC-MS) analysis. The collected urine samples underwent extraction, enzymatic hydrolysis, and derivatization before the analyses of GC-MS. The results showed that seven anabolic steroids were found as contaminants in the nutritional supplement, in addition to six that were listed in the ingredients by the manufacturer. We confirmed previous reports that administration of the OTC supplement could produce a positive urine test for nandrolone metabolites. Furthermore, the results from excretion studies showed that 19-NA and 19-noretiocholanolone (19-NE) were present in urine after consuming the nutritional supplement, nandrolone, 19-nor-4-androsten-3,17-dione, 19-nor-4-androsten-3beta,17beta-diol, and 19-nor-5-androsten-3beta,17beta-diol. The 19-NA concentrations in urine were generally higher than that of 19-NE (19-NA/19-NE ratio > 1.0) especially during the early stage of excretion, that is, before 6 h post-administration. After this period of time, the concentrations of 19-NA and 19-NE fluctuated and might even have reversed (19-NA/19-NE ratio < 1.0) in their ratio, that is, higher yield in 19-NE than that in 19-NA. On the basis of this study, we postulate that some doping violations of nandrolone could be attributed by indiscriminate administration of the OTC nutritional supplements that contained 19-norsteroids.  (+info)

Unintentional doping through the use of contaminated nutritional supplements. (8/29)

OBJECTIVE: To determine whether the intake of contaminated nutritional supplements could cause an athlete to fail a dope test. DESIGN: A contaminated nutritional supplement was used, identified in an ongoing study screening over-the-counter nutritional supplements. One capsule of the supplement, containing small amounts of 19-nor-4-androstenedione and 4-androsten-3,17-dione, not listed on the label, was administered to 5 healthy male volunteers. Fractional urine collection was done at prescribed intervals. Outcome measures. The samples were analysed using gas chromatography/mass spectrometry (GC/MS). Samples containing 19-norandrosterone, the main metabolite of 19-nor-4-androstenedione, were quantified using GC/MS. RESULTS: All the volunteers had urinary concentrations of 19-norandrosterone above the World Anti-Doping Agency threshold of 2 ng/ml from 2 hours post administration. In 2 volunteers 19-norandrosterone above the threshold value could still be detected beyond 36 hours post administration. The highest concentration of 19-norandrosterone found in a sample was 54.6 ng/ml at 8 hours post administration. CONCLUSION: The results of this study showed that the intake of microgram amounts of a prohibited substance in a nutritional supplement could cause an athlete to fail a dope test.  (+info)

Androstenediols are endogenous steroid hormones that are produced in the body from dehydroepiandrosterone (DHEA) and DHEA sulfate (DHEAS), which are secreted by the adrenal glands. There are two major types of androstenediols: 5-androstenediol and 4-androstenediol. These hormones can be further metabolized into testosterone and estrogens, making them important intermediates in steroid hormone synthesis.

5-androstenediol is a weak androgen that can be converted to testosterone in peripheral tissues, while 4-androstenediol has little known biological activity. Both of these compounds have been studied for their potential role in various physiological processes, including sexual differentiation, bone metabolism, and aging. However, more research is needed to fully understand their functions and clinical significance.

It's worth noting that androstenediols are also sometimes referred to as "prohormones" because they can be converted into active steroid hormones in the body. Some athletes and bodybuilders have used synthetic forms of these compounds as performance-enhancing drugs, although their use is banned by many sports organizations due to concerns about potential health risks and unfair advantages in competition.

... androstenediols MeSH D04.808.054.079.429.154.050 - androstenediol MeSH D04.808.054.079.429.154.349 - fluoxymesterone MeSH ...
Androstenediols [D04.210.500.054.079.429.154]. *Fluoxymesterone [D04.210.500.054.079.429.154.349]. *Steroids, Fluorinated [ ...
... androstenediols MeSH D04.808.054.079.429.154.050 - androstenediol MeSH D04.808.054.079.429.154.349 - fluoxymesterone MeSH ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
Aged, Androgens, Androstenediols, Androstenedione, Case-Control Studies, Dehydroepiandrosterone Sulfate, Dihydrotestosterone, ...
A potent androgenic steroid and major product secreted by the LEYDIG CELLS of the TESTIS. Its production is stimulated by LUTEINIZING HORMONE from the PITUITARY GLAND. In turn, testosterone exerts feedback control of the pituitary LH and FSH secretion. Depending on the tissues, testosterone can be further converted to DIHYDROTESTOSTERONE or ESTRADIOL ...
Androstenediols [D04.210.500.054.079.429.154] * Cyanoketone [D04.210.500.054.079.429.320] * Dehydroepiandrosterone [D04.210. ...
Tags: *Androstenediols/adverse effects, *Androstenedione/adverse effects, *Dehydroepiandrosterone/adverse effects, *Doping in ...
Androstenediols / adverse effects * Androstenediols / pharmacology* * Androstenedione / adverse effects * Androstenedione / ...
Androstenediols / adverse effects Actions. * Search in PubMed * Search in MeSH * Add to Search ...
Androstenediols,N0000008015, Ethylene Glycols,N0000008014, Androstanols,N0000008013, Androstadienes,N0000008012, Ethylamines, ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
Androstenediols Preferred Term Term UI T002198. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1975). ... Androstenediols [D04.210.500.054.079.429.154] * Androstenediol [D04.210.500.054.079.429.154.050] * Fluoxymesterone [D04.210. ... Androstenediols Preferred Concept UI. M0001112. Registry Number. 0. Scope Note. Unsaturated androstane derivatives which are ... Androstenediols. Tree Number(s). D04.210.500.054.079.429.154. Unique ID. D000734. RDF Unique Identifier. http://id.nlm.nih.gov/ ...
Androstenediols Preferred Term Term UI T002198. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1975). ... Androstenediols [D04.210.500.054.079.429.154] * Androstenediol [D04.210.500.054.079.429.154.050] * Fluoxymesterone [D04.210. ... Androstenediols Preferred Concept UI. M0001112. Registry Number. 0. Scope Note. Unsaturated androstane derivatives which are ... Androstenediols. Tree Number(s). D04.210.500.054.079.429.154. Unique ID. D000734. RDF Unique Identifier. http://id.nlm.nih.gov/ ...
Androstenediols (1975). Public MeSH Note:. 2004; see ANDROST-5-ENE-3 BETA,17 BETA-DIOL 1998-2003, see 5-ANDROSTENE-3,17-DIOL ... 1991-1997, see ANDROSTENEDIOLS 1976-1990. History Note:. 2004 (1976); use 5-ANDROSTENE-3,17-DIOL 1991-1997, use ANDROSTENEDIOLS ...
Androstenediols. Unsaturated androstane derivatives which are substituted with two hydroxy groups in any position in the ring ... Androstenediol D4.808.54.79.429.154.50 D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429 ... Androstenediol D4.808.54.79.429.154.50 D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
D4.210.500.54.79.429.154.50 Androstenediols D4.808.54.79.429.154 D4.210.500.54.79.429.154 Androstenedione D4.808.54.79.329 ...
Androstenediols Androstenedione Androstenes Androstenols Androsterone Anecdotes Anecdotes as Topic Anelloviridae Anemarrhena ...

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