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PubMed2002

Effects of androstenedione administration on epitestosterone metabolism in men.

Androstenedione is a steroid hormone sold over-the-counter to individuals who expect that it will enhance strength and athletic performance. Endogenous androstenedione is the immediate precursor of testosterone. To evaluate the metabolism of oral androstenedione, we randomly assigned 37 healthy men to receive 0 (group 1), 100 mg (group 2), or 300 mg (group 3) of androstenedione in a single daily dose for 7 days. Eight-hour urines were collected 1 day before the start of androstenedione, and on days 1 and 7. Using gas chromatography-mass spectrometry, we measured excretion rates of glucuronide-conjugated epitestosterone, its putative precursor (E-precursor), and metabolites (EM-1 and EM-2), and we evaluated possible markers of androstenedione administration. Day 1 and 7 rates were not different: the means were averaged. The means (microg/h) for groups 1, 2, and 3, respectively were, for epitestosterone 2.27, 7.74, and 18.0; for E-precursor, 2.9, 2.0, and 1.5; for EM-1/E-precursor 0.31, 1.25, and 2.88; for EM-2/E-precursor 0.14, 0.15, and 1.15; for testosterone/epitestosterone (T/E) 1.1, 3.5, and 3.2. Epitestosterone, EM-1, and EM-2 excretion was greater in groups 2 and 3 versus group 1 (0.0001 < P < 0.03), as were EM-1/E-precursor, EM-2/E-precursor, and T/E. E-precursor excretion was lower in groups 2 (P = 0.08) and 3 (P = 0.047) versus group 1. Androstenedione increases excretion of epitestosterone and its two metabolites, while decreasing that of its precursor. Elevated ratios of EM-1- and EM-2/E-precursor, and the presence of 6alpha-hydroxyandrostenedione are androstenedione administration markers.

Adult↗

PubMed2003

Epitestosterone.

Epitestosterone has been identified as a natural component of biological fluids of several mammals including man. For a long time it was believed that it is a metabolite without any hormonal activity and without any marked relationship to the hormonal state in health and disease. Neither the biosynthetic pathway nor the site of its formation in man have been unequivocally confirmed to date. It apparently parallels the formation of testosterone (T), but on the other hand its concentration is not influenced by exogenous administration of testosterone. This fact creates the basis of the present doping control of testosterone abuse. In 1989 an observation was presented in a dermatological study that epitestosterone exerts an effect counteracting the action of testosterone on flank organ of Syrian hamster. Further studies showed that a complex action consisting of competitive binding of epitestosterone to androgen receptor, of inhibition of testosterone biosynthesis and its reduction to dihydrotestosterone and of antigonadotropic activity could be demonstrated in rat, mice and human tissues. It can be presumed that epitestosterone as a natural hormone can contribute to the regulation of such androgen dependent events as, e.g. the control of prostate growth or body hair distribution.

Androgen Antagonists↗

PubMed1999

Determination of testosterone:epitestosterone ratio after pentafluorophenyldimethylsilyl-trimethylsilyl derivatisation using gas chromatography-mass spectrometry in equine urine.

A highly specific method is described for measuring the testosterone:epitestosterone ratio in equine urine by gas chromatography-mass spectrometry (GC-MS) with stable isotope internal standards. The procedure was based on Serdolit Pad-1 resin extraction, enzymatic hydrolysis, and chemical derivatisation prior to instrumental analysis. The mixed derivatives, 3-trimethylsilyl-17-pentafluorophenyldimethylsilyl ether (3-TMS-17-flophemesyl) testosterone and epitestosterone, were found to have excellent analytical properties. The specificity of the derivatisation method exploits a unique feature of steroids: the selective exchange of the alcoholic flophemesyl ether for the trimethylsilyl ether. The sensitivity and specificity of the mixed 3-TMS-17-flophemesyl derivatives allow adequate determinations of testosterone and epitestosterone, even in urine from mares, in 5 ml samples. The repeatability of testosterone and epitestosterone was 6.2 and 5.7%, respectively, and their reproducibility was in the range of 6.4-8.7%.

Animals↗

PubMed1996

Plasma and urinary markers of oral testosterone misuse by healthy men in presence of masking epitestosterone administration.

There is a potential need for the official criterion of testosterone abuse in sport (the urinary concentration ratio of testosterone glucuronide/epitestosterone glucuronide, TG/EG > 6) to be backed-up by some complementary markers, more particularly in cases of physiologically high TG/EG and when there is suspicion of joint administration of testosterone and epitestosterone. Testosterone, epitestosterone, their glucuro- and sulfoconjugates, 5-androstene-3 beta, 17 alpha-diol glucuronide and 17-hydroxyprogesterone have been analysed by isotope dilution-gas chromatography-mass spectrometry in plasma and urine of seven subjects supplemented with a single oral dose of undecanoates of testosterone and epitestosterone (respectively 40 mg and 1.5 mg). Adequate plasma criteria for testosterone abuse were the ratios of testosterone glucuronide/17-hydroxyprogesterone and testosterone glucuronide/testosterone which increased significantly above basal values for up to 10 h. The same trend was observed for the ratio of urinary glucuronides of testosterone/5-androstene-3 beta, 17 alpha-diol, while TG/EG was not affected by simultaneous administration of epitestosterone. One subject with low basal TG/EG failed to respond to testosterone administration by any significant increase of analysed parameters.

Adult↗

PubMed1979

Epitestosterone in the plasma of the goat during pregnancy and at parturition.

Epitestosterone, a product of the metabolism of androstenedione by the caprine placenta in vitro, is present in the plasma of the pregnant goat. The maternal concentrations of both epitestosterone and unconjugated oestrogens (mostly oestradiol-17 alpha) in the blood increased before parturition and dropped post partum. Measurement of arteriovenous differences at term indicated that epitestosterone was secreted by the uterus; its production was not dependent on the presence of corpora lutea. It is suggested that the concentration of epitestosterone (+ androstenedione + oestrogens) in maternal plasma may be used as an indicator of placental C-17,20 lyase activity; the slight rise in the concentration of these compounds prepartum suggests a relatively small increase in flow through this enzyme.

Animals↗

PubMed1993

Epitestosterone--a hormone or not.

Epitestosterone is a natural component of biological fluids of several mammals including man. For a long time it has been believed that it is a metabolite without any hormonal activity and without any marked relationship to the hormonal state in health and disease. The biosynthetic pathway as well as the site of its formation in man has not been unequivocally confirmed until now. It apparently parallels the formation of testosterone but, on the other hand, its concentration is not influenced by exogenously administered testosterone. This fact creates the basis of the present doping control of testosterone abuse. In 1989 an observation was presented in a dermatological study that epitestosterone has an effect counteracting the action of testosterone on flank organ of Syrian hamster. Further studies showed that a complex action consisting of competitive binding of epitestosterone to androgen receptor, of inhibition of testosterone biosynthesis and its reduction to dihydrotestosterone and of antigonadotropic activity could be demonstrated in rat, mice and human tissues. It can be presumed that epitestosterone as a natural hormone can contribute to the regulation of androgen dependent events as e.g. to the control of growth of prostate or body hair distribution.

Animals↗

PubMed1996

Antirenotropic action of antiandrogens cyproterone acetate, casodex, flutamide and epitestosterone.

The antirenotropic activities of three antiandrogens which are frequently used in the clinical praxis (cyproterone acetate, flutamide and casodex) and of natural endogenous antiandrogen epitestosterone were compared. The substances were administered in oil intraperitoneally to intact male mice. The weight of kidneys was decreased most effectively by casodex and epitestosterone, though the antiandrogenic activity expressed by the decreased weight of seminal vesicles was confirmed in all preparation tested, except for flutamide. Only epitestosterone significantly reduced the level of plasma testosterone, whereas casodex increased testosterone level in plasma. LH level was decreased by testosterone propionate and epitestosterone significantly, but about 50 percent increase in the mean LH level in casodex treated animals did not reach the statistical significance.

Journal Article↗

PubMed1995

The effect of epitestosterone on spermatogenesis in rats.

The effect of 3-week treatment with increasing doses of endogenous steroid with antiandrogenic properties, epitestosterone (ET), on the spermatogenesis was studied in adult male rats by flow cytometry and correlated with the effect on gonadotropin gene expression and secretion, on testosterone and dihydrotestosterone plasma levels and on the weight of testes and prostates. Epitestosterone was administered to the rats by means of silastic capsules of different lengths filled with the steroid. A decrease of the number of total spermatides in the epitestosterone treated animals was observed. In the group with the lowest dose of ET the number of elongated spermatides was significantly reduced. The number of germ cell types and their relative proportions were correlated with the endocrine parameters reported previously. Significant negative correlation between the pituitary content of LH and total number of germ cells per 1 g of testicular tissue and of the number of spermatides/g and between testosterone level in serum and the number of diploid cells in the animals treated with higher doses of ET was found. In the group with highest ET dose a negative correlation of diploid cells and serum dihydrotestosterone was observed, too. The naturally occurring antiandrogen epitestosterone can be considered as one of the endogenous factors influencing spermatogenesis.

Journal Article↗

PubMed2000

Direct measurement of urinary testosterone and epitestosterone conjugates using high-performance liquid chromatography/tandem mass spectrometry.

Measurement of the ratio of testosterone (T) and epitestosterone (E) in urine has been used as an indication of 'natural' steroid supplementation for a decade. The direct measurement of the glucuronide and sulfate conjugates of testosterone and epitestosterone by high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS/MS) should resolve a number of issues regarding unusual metabolism due to either genetic disposition or attempts to avoid detection of abuse. Determination of nanomoles per liter (0.1 ppb) concentrations of analytes in a complex biological matrix by HPLC/MS/MS is complicated by sample matrix-specific ion suppression during ESI. Deuterated internal standards of all compounds were used to overcome the effects of suppression. Comparison of the HPLC/MS/MS method with a two-part gas chromatographic/mass spectrometric method showed statistical equivalence in urine samples. Analysis of urine samples with elevated T-glucuronide to E-glucuronide ratios did not show that a significant number could be explained by an elevated excretion of epitestosterone sulfate. The HPLC/MS/MS method was also used further to characterize genetic and metabolic factors that give rise to unusual T/E ratios.

Adolescent↗

PubMed2000

Beta-hydroxy beta-methylbutyrate (HMB) supplementation does not influence the urinary testosterone: epitestosterone ratio in healthy males.

Six healthy, recreationally active, males undertook two weeks supplementation with beta-Hydroxy beta-Methylbutyrate (HMB). Supplementation was in capsule form with 3 g consumed each day in three even doses of 1 g at main meals. Mid stream urine samples were collected prior to, as well as, after one and two weeks of supplementation and subsequently analysed for testosterone and epitestosterone. The testosterone: epitestosterone ratio was not affected by 2 weeks of HMB supplementation (mean +/- SD baseline 1.02 +/- 0.68; week one 0.98 +/- 0.61; week two 0.92 +/- 0.62). Our results support the claim that supplementation with HMB at the doses recommended will not influence the urinary testosterone: epitestosterone ratio and thus not breach doping policies of the International Olympic Committee for exogenous testosterone or precursor administration.

Adult↗

PubMed1999

Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse.

OBJECTIVE: The ratio of urinary testosterone (T) to epitestosterone (EpiT) is used to detect T abuse in sport. Also, plasma or urinary concentrations of EpiT have been measured to assess testicular steroidogenesis during hormonal male contraception. Further investigations are required to evaluate the relative contributions of the testis and adrenal to EpiT production. To this purpose, we have compared basal urinary EpiT glucuronide and plasma EpiT and the response to synthetic adrenocorticotrophic hormone (ACTH) stimulation between eugonadal and hypogonadal men. DESIGN AND SUBJECTS: The basal urinary excretion rate of EpiT glucuronide was determined in 34 eugonadal men. Six men, clinically diagnosed as hypogonadal, and 6 out of the 34 eugonadal men previously described, received an intramuscular injection of synthetic ACTH depot (1 mg) at 0800 h on two consecutive days. Blood samples were collected prior to and then at 1.5, 8, 24, 25.5, 32 and 48 h with respect to the first administration (0 h). 24-h urine specimens were collected from 0800 h on days 1 and 2 (baseline) and 3 and 4 (stimulation). MEASUREMENTS: Plasma EpiT, T and cortisol were measured by RIA and urinary EpiT and T, following glucuronide hydrolysis, by gas chromatography-mass spectrometry (extract combines aglycones with a minor amount of urinary free steroids). RESULTS: Basal excretion rates of EpiT glucuronide in eugonadal men (range: 62-751 nmol/24 h) were considerably greater than in hypogonadal men (range: 3-34 nmol/24 h). Mean basal plasma EpiT in eugonadal men (1.32 +/- 0.08 nmol/l) were greater than in hypogonadal men (0.68 +/- 0.04 nmol/l). In each group, synthetic ACTH stimulation increased plasma cortisol 4-fold. In eugonadal men, plasma and urinary EpiT were unchanged whereas plasma and urinary T glucuronide decreased in response to ACTH. In hypogonadal patients, ACTH increased plasma and urinary EpiT while plasma T remained unchanged. CONCLUSION: The testes are the major source of epitestosterone, the adrenal contribution being relatively modest. Following adrenal stimulation, urinary epitestosterone glucuronide increases considerably in hypogonadal men but this increase is masked in eugonadal men because testicular production is probably suppressed by the ACTH-induced rise in cortisol. Activation of the adrenal cortex results in no change or only a small decrease in the urinary T/EpiT ratio in eugonadal men.

Adrenal Glands↗

PubMed1997

Inhibition of rat renal and testicular 11 beta-hydroxysteroid dehydrogenase by some antihypertensive drugs, diuretics, and epitestosterone.

With regard to previous finding of an inhibitory activity of furosemide on 11 beta-hydroxysteroid dehydrogenase, 16 other commonly used diuretics have been tested as to their ability to inhibit rat renal, and in four instances also testicular 11 beta-hydroxysteroid dehydrogenase, using glycerrhetinic acid as a standard. In addition, epitestosterone has been tested as well, with respect to its recently demonstrated inhibitory activity on several other enzymes of androgen biosynthesis. Besides corticosterone, 11 beta-hydroxy-4-androstene-3,17-dione has been used as a substrate. Of all drugs studied, quinapril, dihydralazin, trandolapril, metipamid, methyldopa, betaxolol only appeared to be weak inhibitors of 11 beta-hydroxysteroid dehydrogenase, with an inhibitory activity 10-28% of that of glycyrrhetinic acid. Using corticosterone as a substrate, epitestosterone displayed a weak inhibitory activity with Ki 850, 1200 nmol/l and Vmax 2420, 3900 nmol/l.min for renal and testicular enzyme, respectively. In contrast to kidneys, the testicular 11 beta-hydroxysteroid dehydrogenase accepted also 11 beta-hydroxy-4-androstene-3,17-dione as a substrate, which could be inhibited by epitestosterone (Ki 1490 nmol/l, Vmax 1150 nmol/l.min). The results represent further evidence for different substrate specificity of renal and testicular 11 beta-hydroxysteroid dehydrogenase.

11-beta-Hydroxysteroid Dehydrogenases↗

PubMed2001

Antiandrogenic activity of epitestosterone in male mice in vivo.

Steroidal antiandrogen epitestosterone was administered to intact male mice and its effect on seminal vesicles, kidney, femoral bones and circulating calcium, phosphate, testosterone and LH were compared with controls and castrated animals. Epitestosterone was previously reported as an inhibitor the binding of androgens to their receptors, an inhibitor of the formation of dihydrotestosterone from testosterone and a modulator of estradiol-estrone conversion. In the present study it is demonstrated that it decreased the weight of kidney, seminal vesicles and bone density, ash weight and calcium and phosphate content of femoral bone tissue significantly, although not to the values as low as those seen in castrated animals. Thus in mice epitestosterone effects could be classified as antiandrogenic.

Androgen Antagonists↗

PubMed1991

Observations on the biological activity of epitestosterone.

Epitestosterone, a 17 alpha-epimer of testosterone is a normal constituent of body fluids in many species including man. It has long been believed that it is devoid of any biological significance. However, it is now demonstrated that in in vivo experiments on castrated male mice it counteracts the action of testosterone on androgen-dependent organs. In vitro experiments show that on the overall antiandrogenicity of epitestosterone participate true antiandrogenic action due to the binding to androgen receptors, strong 5 alpha-reductase inhibiting activity as well as a weak antigonadotropic activity. Epitestosterone is devoid of any embryotoxicity as checked by chick embryo-toxicity screening test.

5-alpha Reductase Inhibitors↗

PubMed1989

[Does epitestosterone function as an endogenous antiandrogen?].

The action of the endogenous steroid epitestosterone administered to castrated male mice substituted with testosterone propionate is manifested by reduced weight increments and a reduced relative weight of their seminal vesicles and kidneys. Epitestosterone in vitro displaces androgens from their bond with receptors in cytosol from rat prostates and markedly inhibits the testosterone transformation to the more effective androgen dihydrotestosterone. Epitestosterone can be thus defined as a true endogenous antiandrogen; to its action at the receptor level a potent inhibitory effect on 5 alpha-reductase must be added.

Androgen Antagonists↗

PubMed1979

Urinary testosterone and epitestosterone excretions in women with idiopathic hirsutism.

Urinary testosterone and epitestosterone were determined in 90 normal healthy women and in 90 women with idiopathic hirsutism, both groups aged between 16 and 46 years. Testosterone and epitestosterone excretion values were above the normal range in 27 of the 90 hirsute women (30%), and these 27 women had much more prominent hair growth than the others. When these results were statistically analysed according to the age groups or for all ages as a whole, they were found to be highly significant (P less than 0.0005). Therefore, it is concluded that the estimation of urinary testosterone and epitestosterone could be meaningfully applied to study the androgen status of hirsute women.

Adolescent↗

PubMed1981

[Age-dependent changes in epitestosterone urinary excretion in man].

Previous studies carried out by the Authors had shown an increased urinary excretion of epitestosterone, a poorly active androgen mostly believed to be of adrenal origin, after HCG administration to presenescent and aging subjects. Purpose of this study was to ascertain whether or not this held in the young too. Testosterone excretion sharply decreased after the age of 60 (P less than 0,001); 17 KS on the other hand, decreased progressively in such a way that the aging group showed significantly lower (p less than 0,05) excretion rates than the only young-adult group. ET excretion decreased steadily but not significantly with age. ET showed a very good correlation to T (p less than 0,01) both under basal and poststimulatory conditions in each of the three age groups. ET percent increase showed a good correlation (p less than 0,01) to T percent increase only in young-adult and presenescent people, not in the elderly. Poor was the correlation between ET percent increase and 17 KS percent increase. Thus ET excretion pattern showed to be somewhat different from that of T and very different from that of 17 KS. As a conclusion (a) epitestosterone excretion rate seems to decrease steadily but not significantly with age; (b) epitestosterone probably is not mainly secreted by the adrenal gland. A major source may be the testis, but liver, prostate and blood red cells metabolism are not definitely ruled out.

17-Ketosteroids↗

PubMed1989

Epitestosterone--an endogenous antiandrogen?

Epitestosterone (17 alpha-hydroxy-4-androsten-3-one), a normal constituent of human plasma and urine, prevents the testosterone induced changes in body weight and in organ weights of seminal vesicles and kidney of castrated male mice. It competes with methyltrienolone in the binding to rat prostate cytosol (Ki = 29.8 nmol.l-1. It inhibits also the activity of 5 alpha-reductase from rat prostate pellet (Ki = 1.2 mumols.l-1). Epitestosterone can be considered as a weak antiandrogen in the term of displacement of androgen from receptor binding and as an efficient inhibitor of 5 alpha-reductase.

Animals↗