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PubMed1983

Progesterone, androstenedione, testosterone, 5 alpha-dihydrotestosterone and androsterone concentrations in specific regions of the human brain.

The concentrations of progesterone, androstenedione, testosterone, 5 alpha-dihydrotestosterone and androsterone were determined in tissue samples from the human hypothalamus, anterior pituitary, pineal, amygdala and parietal cortex, taken at autopsy from male (n = 4) and female cadavers (n = 4) of various ages. The measurements were performed using radioimmunoassays for the individual steroids after the chromatographic purification of solvent extracts of tissue samples on Lipidex-5000TM. Preliminary qualitative analyses of the chromatographic profiles of various steroids by radioimmunoassay demonstrated the presence of these steroids in various regions of the brain, but an immunoreactive peak corresponding to 17-hydroxyprogesterone was not found. The concentrations (ng/g tissue wet wt.) of all steroids measured were either very low or below the limit of detection in brain tissues taken from male and female infants. In the adult brain, there was no difference in the distribution of steroids between the various regions studied. There was no sex difference in the brain tissue steroid concentrations, with the exception of testosterone which was clearly much higher in brain tissues from men as compared to women. Although testosterone was undetectable in most samples taken from adult women. 5 alpha-dihydrotestosterone could be measured in almost all samples, which suggests that this is the most important androgen in the human brain. When brain tissue steroid levels are compared with serum concentrations, it can be postulated that a state of equilibrium exists between the fraction of serum steroids which are not bound to high-affinity binding proteins and the amount of steroids in brain tissues.

17-alpha-Hydroxyprogesterone↗
PubMed1975

Androsterone. The structure by force-field calculations.

The structure of androsterone was calculated by the force-field (molecular mechanics) method. Plots of the calculated structure are compared with those of the X-ray structure, and found to have all of the atoms in the same positions to within 0.1 A. The regular Dreiding model structure differs substantially from these calculated and experimental structures, atomic positions being up to 0.9 A removed from where they should be.

Androsterone↗
PubMed1977

Radioimmunoassays for androsterone, 5alpha-androstane-3alpha, 17beta-diol and 5alpha-androstane-3beta, 17beta-diol.

Androsterone (3alpha-hydroxy-5alpha-androstan-17-one), 5alpha-androstane-3alpha, 17beta-diol and 5alpha-androstane-3beta, 17beta-diol were conjugated at C-16 through sulfur to bovine and human serum albumin. Rabbits injected with these conjugates produced antibodies suitable for radioimmunoassays of these hormone metabolites. Samples were purified on Sephadex LH-20 columns. Levels of these steroids were measured in a rat blood serum pool and in ovarian tissue extract pools.

Androstane-3,17-diol↗
PubMed1978

Disulphates of 16-oxygenated ketonic C19 steroids as biliary metabolities of androsterone sulphate in female rats.

The chemical synthesis of 16beta-hydroxyandrosterone was described preparatory to studies of the disulphates of the 16-oxygenated ketonic C19 steroids present in the bile of female rats dosed with [3H]androsterone sulphate. The biliary metabolites were separated by chromatography on Sephadex LH-20 to afford monosulphate and diconjugate fractions. After solvolysis of the diconjugate fraction, the liberated steroids were separated by partition chromatography on Celite 545 and analyzed by gas chromatography-mass spectometry. In addition to 3alpha, 17beta-dihydroxy-5alpha-androstan-16-one isolated previously, 16beta-hydroxyandrosterone was identified as a disulphate.

Androsterone↗
PubMed2005

3Beta-alkyl-androsterones as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: inhibitory potency in intact cells, selectivity towards isoforms 1, 2, 5 and 7, binding affinity for steroid receptors, and proliferative/antiproliferative activities on AR+ and ER+ cell lines.

Type 3 17beta-hydroxysteroid dehydrogenase (17beta-HSD) is involved in the biosynthesis of the potent androgen testosterone (T), which plays an important role in androgen-sensitive diseases. In an attempt to design compounds to lower the level of T, we designed androsterone (ADT) derivatives substituted at the position 3beta as inhibitors of type 3 17beta-HSD, and then selected the eight most potent ones (compounds 1-8) for additional studies. In an intact cell assay, they inhibited efficiently the conversion of natural substrate 4-androstene-3,17-dione into T, although they were less active in intact cells (IC50 approximately 1 microM) than in homogenated cells (IC50=57-100 nM). A study of the inhibitory potency with four other 17beta-HSDs revealed they were selective, since they do not inhibit reductive types 1, 5 and 7, nor oxidative type 2. Interestingly, they did not show any binding affinity for steroid receptors (androgen, estrogen, glucocorticoid and progestin). Only two inhibitors, 3beta-phenyl-ADT (5) and 3beta-phenylmethyl-ADT (6) showed some proliferative activities on an AR+ cell line and on an ER+ cell line, but their effects were not mediated through the androgen or estrogen receptors. This study identified selective inhibitors of type 3 17beta-HSD acting through a mixed-type inhibition, and devoid of non-suitable androgenic and estrogenic proliferative activities. The more potent inhibitors were 3beta-hexyl-ADT (2), 3beta-cyclohexylethyl-ADT (4) and 3beta-phenylethyl-ADT (7).

17-Hydroxysteroid Dehydrogenases↗
PubMed2003

A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.

A facile six-step synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide (1) starting from epiandrosterone (2) in 63% yield is described and compared with several alternative synthetic pathways. Compound 1 can be used as an internal standard in screening procedures for anabolic steroids to monitor the hydrolysis step of the steroid glucuronides prior to gas chromatography-mass spectrometry (GC-MS) analysis. Thus, a time consuming solid-phase extraction step to remove possible hydrolysis inhibitors can be omitted.

Anabolic Agents↗
PubMed2000

Androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase.

Androsterone derivatives substituted at position 3 were synthesized starting from dihydrotestosterone in a short sequence of reactions. They proved to be potent inhibitors (IC50 = 57-147 nM) of type 3 17beta-hydroxysteroid dehydrogenase, a key enzyme of steroidogenesis, which catalyzes the transformation of androstenedione to steroid active androgen testosterone.

17-Hydroxysteroid Dehydrogenases↗
PubMed1965

Dehydrogenation of androsterone by purified 3-alpha-hydroxy steroid-dependent nicotinamide-adenine dinucleotide (phosphate)-transhydrogenating enzyme of rat liver.

1. An enzyme from rat liver, catalysing 3alpha-hydroxy steroid-dependent NAD(P) transhydrogenation and NAD-linked and NADP-linked dehydrogenation of 3alpha-hydroxy steroids, has been purified 100-fold by chromatography on DEAE-cellulose and calcium phosphate gel. 2. No separation of these activities into different protein fractions has been achieved. 3. The properties of the enzyme in catalysing NAD-linked and NADP-linked dehydrogenation have been compared, with androsterone as substrate. Differences were found in pH optima, affinity for coenzyme and steroid, equilibrium constants and effects of salts. 4. NAD-linked dehydrogenation is inhibited by NADPH(2) but is protected from this inhibition by chloride, which alone is itself an inhibitor. 5. The relevance of these findings to the problem of the number of enzymes involved in catalysis of 3alpha-hydroxy steroid-dependent transhydrogenation is discussed.

Androsterone↗
PubMed1982

Classification and genetic expression of Wistar rats with high and low hepatic microsomal UDP-glucuronosyltransferase activity towards androsterone.

Male and female Wistar rats with high and low hepatic microsomal UDP-glucuronosyltransferase activity towards androsterone were classified by partial hepatectomy. The breeding experiments between the classified high-activity and low-activity rats show that the genetic expression of the high transferase activity is inherited in an autosomal dominant fashion.

Androsterone↗
PubMed1984

Plasma dehydroepiandrosterone, dehydroepiandrosterone sulphate and androsterone sulphate levels and their interaction with plasma proteins in rheumatoid arthritis.

Female patients with rheumatoid arthritis (RA) in Steinbrocker's II and III rating scale have been examined. They were without steroid treatment at least six months before observation. Plasma protein picture showed hypoalbuminaemia and hyperglobulinaemia. There was no difference relative to controls either in the total (free + protein bound) plasma dehydroepiandrosterone (D) level, or in its distribution with plasma proteins. In the age group of 18 to 45 years, a statistically significant decrease have been observed in the total plasma dehydroepiandrosterone sulphate (DS) level without any change in its distribution in protein binding. Furthermore, low androsterone sulphate (AS) levels were found irrespective of the age of patients. The results gave further information on the pathomechanism resulting in an abnormal androgen hormone pattern of blood and a low metabolite excretion, observed previously in patients with RA:.

Adolescent↗
PubMed2002

Androsterone derivatives substituted at position 16: chemical synthesis, inhibition of type 3 17beta-hydroxysteroid dehydrogenase, binding affinity for steroid receptors and proliferative/antiproliferative activity on Shionogi (AR+) cells.

A series of androsterone (ADT) derivatives substituted at position 16 were efficiently synthesized in short reaction sequences; the ether analogues were also synthesized in the case of the methyl and allyl derivatives. The aim of this study was to develop inhibitors of the steroidogenic enzyme type 3 17beta-hydroxysteroid dehydrogenase and then evaluate their ability to inhibit this activity in transfected HEK-293 cells. For each compound we measured the percentage of inhibition of the transformation of 4-androstene-3,17-dione, the natural substrate of this steroidogenic enzyme, into the active androgen testosterone. The synthesized compounds proved to be weak inhibitors of this enzyme, but interestingly, these ADT derivatives do not bind to androgen, estrogen, glucocorticoid, and progestin receptors, suggesting no unsuitable receptor-mediated effects. One exception, 16alpha-(3'-bromopropyl)-5alpha-androstane-3alpha,17beta-diol, the only compound bearing a hydroxy group at position 17beta instead of a ketone, showed a strong binding affinity for the androgen receptor (70% at 1 microM) and also exhibited an antiproliferative activity on Shionogi (AR+) cells (86% at 1 microM), which was comparable to that of hydroxyflutamide, a pure antiandrogen (100% at 1 microM).

17-Hydroxysteroid Dehydrogenases↗
PubMed1991

Isolation, sequence, and developmental expression of rat UGT2B2: the gene encoding a constitutive UDP glucuronosyltransferase that metabolizes etiocholanolone and androsterone.

The UDP glucuronosyltransferase gene UGT2B2 is constitutively expressed in rat liver, and the enzyme has been shown to conjugate glucuronic acid with various endogenous steroids, especially etiocholanolone and androsterone. We have cloned and sequenced much of the UGT2B2 gene and 5'-flanking (247 bp) and 3'-flanking (734 bp) regions. The gene contains six exons spanning about 15.3 kb. Translation begins at nucleotide 36 of exon 1 and terminates with 280 coding nucleotides into exon 6, encoding a protein of 530 amino acids (calculated Mr of the unmodified chain = 60,913). We have determined that the UGT2B2 full-length cDNA is 1,974 bp. Northern hybridization revealed that the hepatic UGT2B2 transcript is detectable 4 days before birth, becomes markedly elevated in the neonate, and is even further increased at 3 and 12 weeks of age in the liver of both male and female rats.

Amino Acid Sequence↗
PubMed1994

Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion.

OBJECTIVE: Recent evidence suggests that androstanediol glucuronide (AG), a metabolite of dihydrotestosterone (DHT) formed in skin, is frequently elevated in hirsute women, presumably reflecting enhanced 5 alpha-reductase activity. An alternative method of demonstrating 5 alpha-reductase activity is the androsterone (A)/aetiocholanolone (E) ratio in urine. A and E are the 5 alpha- and 5 beta-reduced metabolites, respectively, of androstenedione, which is the principal metabolite of dehydroepiandrosterone (D). Although serum AG and the urinary A/E ratio have both been considered valid methods for assessing 5 alpha-reductase activity, the two have not been previously compared in hirsute women. The present study was undertaken to assess 5 alpha-reductase activity in hirsute patients as determined by these two different methods. PATIENTS AND MEASUREMENTS: We surveyed 47 untreated women (ages 17-33) with various degrees of hirsutism. Serum testosterone, bioavailable testosterone, dehydroepiandrosterone sulphate, and AG were determined. Additionally, A, E and D were measured in 24-hour collections of urine. RESULTS: For the 47 women, 37 had elevated blood levels of AG (17.4 +/- 2.2, mean +/- SEM; normal < 8 nmol/l), but only 18 of these had an increased urinary A/E ratio (> 1.5). All but one of the remainder had elevated urinary and/or serum androgen levels. Overall, no significant correlation between AG and A/E was observed. There was a highly significant correlation between AG in serum and A in urine (r = 0.82, P < 0.001). AG was also positively related to dehydroepiandrosterone sulphate (r = 0.64; P < 0.005), bioavailable testosterone (r = 0.6; P < 0.001), aetiocholanolone (r = 0.58; P < 0.001) and total testosterone (r = 0.52; P < 0.01). In contrast, A/E was not significantly related to androgen production. CONCLUSIONS: There is a poor correlation between AG and the A/E ratio in hirsute women. Although AG may be raised by increased 5 alpha-reductase activity, it is probably also affected by the presence of elevated androgens regardless of 5 alpha-reductase activity.

3-Oxo-5-alpha-Steroid 4-Dehydrogenase↗
PubMed2005

Anticonvulsant activity of androsterone and etiocholanolone.

PURPOSE: Men with epilepsy often have sexual or reproductive abnormalities that are attributed to alterations in androgen levels, including subnormal free testosterone. Levels of the major metabolites of testosterone-androsterone (5alpha-androstan-3alpha-ol-17-one; 5alpha,3alpha-A), a neurosteroid that acts as a positive allosteric modulator of GABA(A) receptors, and its 5beta-epimer etiocholanolone (5beta-androstan-3alpha-ol-17-one; 5beta,3alpha-A)-also may be reduced in epilepsy. 5alpha,3alpha-A has been found in adult brain, and both metabolites, which also can be derived from androstenedione, are present in substantial quantities in serum along with their glucuronide and sulfate conjugates. This study sought to determine whether these endogenous steroid metabolites can protect against seizures. METHODS: The anticonvulsant activity of 5alpha,3alpha-A and 5beta,3alpha-A was investigated in electrical and chemoconvulsant seizure models in mice. The steroids also were examined for activity against extracellularly recorded epileptiform discharges in the CA3 region of the rat hippocampal slice induced by perfusion with 55 microM 4-aminopyridine (4-AP). RESULTS: Intraperitoneal injection of 5alpha,3alpha-A-protected mice in a dose-dependent fashion from seizures in the following models (ED50, dose in mg/kg protecting 50% of animals): 6-Hz electrical stimulation (29.1), pentylenetetrazol (43.5), pilocarpine (105), 4-AP (215), and maximal electroshock (224). 5beta,3alpha-A also was active in the 6-Hz and pentylenetetrazol models, but was less potent (ED50 values, 76.9 and 139 mg/kg, respectively), whereas epiandrosterone (5alpha,3beta-A) was inactive (ED50, <or=300 mg/kg). 5alpha,3alpha-A (10-100 microM) also inhibited epileptiform discharges in a concentration-dependent fashion in the in vitro slice model, whereas 5beta,3alpha-A was active but of lower potency, and 5alpha,3beta-A was inactive. CONCLUSIONS: 5alpha,3alpha-A and 5beta,3alpha-A have anticonvulsant properties. Although of low potency, the steroids are present in high abundance and could represent endogenous modulators of seizure susceptibility.

4-Aminopyridine↗
PubMed1973

Androsterone-etiocholanolone ratios in male homosexuals.

Analyses of 24-hour specimens of urine from healthy adult males for androsterone and etiocholanolone produced values which, when calculated as discriminant scores, discriminated between heterosexual and exclusively homosexual individuals. This confirms a previous study.No significant differences were found between heterosexuals and homosexuals in parental ages, secondary sex characteristics, genitalia, anthropometry, 17-ketosteroids, and 17-ketogenic steroids.A significant difference was found between the heterosexual group and homosexual group in the number of homosexual relatives in the immediate and extended families.

17-Ketosteroids↗
PubMed1978

Opiate-like naloxone-reversible effects of androsterone sulfate in rats.

Androsterone sulfate (5alpha-androstan-3alpha-ol-17-one, 3-sodium sulfate) administered to freely moving rats via cerebroventricular cannulae induced analgesia, wet-dog shakes, body jerks, rigidity, Straub tail, hypermotility, excessive grooming, hyperreactivity to stimuli, aggression, escape behavior, EEG spiking, and behavioral and EEG seizures. These responses resemble those produced by certain opiate drugs and by beta-endorphin, an endogenous peptide; they appear during the 5-min infusion period, persist in some cases for several hours, and are diminished by pretreatment with the narcotic antagonist naloxone. These findings indicate that steroid hormones can act upon at least some of the same central pathways influenced by recognized opiate compounds.

Androsterone↗
PubMed1993

Origin and significance of plasma androsterone glucuronide levels: a parameter of adrenal androgen secretion and hepatic 5 alpha-reductase activity.

To evaluate the reliability of plasma androsterone glucuronide (ADTG) as a parameter of androgenicity at the target tissue level, we studied the origin of ADTG in women, by measuring the plasma conversion rate of different possible precursors as well as by measuring ADTG levels in ovariectomized women and women with Addison's disease. In women, ADTG levels reflect essentially adrenal androgen secretion, dehydroepiandrosterone sulfate (DHEAS) being the major precursor, accounting for 70%-80% of ADTG levels. As estimated from the ADTG/DHEAS ratio in hirsute women (increased peripheral 5 alpha-reductase) and hyperthyroid women (increased hepatic 5 alpha-reductase), it appears that hepatic 5 alpha-reductase is a major determinant of the conversion of precursors to plasma ADTG. In men, plasma testosterone and DHEAS appear to contribute to a comparable extent to plasma ADTG levels, as suggested by data obtained in orchidectomized men and men with Addison's disease. In accordance with the role of DHEAS as a precursor, plasma levels of ADTG decrease significantly with age in both men and women. Our data do not support the concept that plasma ADTG levels reflect primarily peripheral androgen formation.

Addison Disease↗
PubMed1993

Evidence for increased androsterone metabolism in some normoandrogenic women with acne.

Increased androgen production from the ovary, adrenal or locally in skin has been implicated in the pathogenesis of acne. Recent data have provided evidence that androsterone (Ao) metabolism is exaggerated in acne and serum metabolites of Ao differentiate between acne and hirsutism in hyperandrogenic women. Here we have extended these studies to normoandrogenic women who have moderate to severe acne. We measured serum ovarian and adrenal androgens as well as the glucuronide and sulfate metabolites of Ao and 3 alpha-androstanediol which reflect, in part, peripheral androgen action. In a group of 15 well-selected normoandrogenic patients with acne, both serum Ao glucuronide (G) and Ao were elevated (P < 0.01; P < 0.05). The ratios of Ao G to androgen precursors of both ovarian and adrenal origin were elevated as was the ratio of Ao G/Ao (P < 0.05). These data suggest that increased Ao metabolism is a specific abnormality found in both normoandrogenic and hyperandrogenic women with acne. Our findings also provide a rationale for antiandrogen therapy at least in some normoandrogenic women with acne.

Acne Vulgaris↗