Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Androstanes”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed1980

The identification and characterization of the C19O3 steroid metabolites of 5 alpha-androstane-3 beta,17 beta-diol produced by the canine prostate: 5 alpha-androstane-3 beta,6 alpha,17 beta-triol and 5 alpha-androstane-3 beta,7 alpha,17 beta-triol.

This study has identified the polar metabolites of 5 alpha-androstane-3 beta-17 beta-diol(3 beta-diol) produced by the canine prostate. The major metabolite is 5 alpha-androstane-3 beta,7 alpha,17 beta-triol(7 alpha-triol) accounting for approximately 80% of the total polar metabolites of 3 beta-diol. The remaining 20% is accounted for exclusively by another triol, 5 alpha-androstane-3 beta,6 alpha,17 beta-triol(6 alpha-triol). This study has also characterized two enzymatic hydroxylase responsible for respective triol formation: 5 alpha-androstane-3 beta,17 beta-diol 6 alpha-hydroxylase(6 alpha-hydroxylase) and 5 alpha-androstane-3 beta,17 beta-diol 7 alpha-hydroxylase(7 alpha-hydroxylase). Both of these irreversible hydroxylases are located in the particulate fraction of the prostate and can utilize either NADH or NADPH as cofactor. Several in vitro steroid inhibitors of these hydroxylases were identified including cholesterol, estradiol and diethylstilbestrol. Neither of the hydroxylases were found to be decreased by castration (3 months) when expressed as activity/DNA. Using a variety of C19 androstane substrates, 6 alpha- and 7 alpha-triol were found to be major components of the total 3 beta-hydroxy-5 alpha-androstane metabolites produced by the canine prostate.

Androstane-3,17-diol↗
PubMed1979

Metabolism of 5 alpha-androstane-3 beta,17 beta-diol to 17 beta-hydroxy-5 alpha-androstan-3-one and 5 alpha-androstan-3 alpha,17 beta-diol in the rat.

Significant metabolism of 5 alpha-androstane-3 beta,17 beta-diol to 17 beta-hydroxy-5 alpha-androstan-3-one was recorded in several tissues and organs from rats and humans. This bioconversion was further investigated in rat testis homogenates. 5 alpha-Androstane-3 beta,17 beta-diol was readily metabolized to 17 beta-hydroxy-5 alpha-androstan-3-one with NAD and/or NADP added as cofactors. When a NADPH generating system was included in the incubation, 5 alpha-androstane-3 beta,17 beta-diol was metabolized to 5 alpha-androstan-3 alpha,17 beta-diol. Only small amounts of 17 beta-hydroxy-5 alpha-androstan-3-one accumulated under the latter condition.

Androstanols↗
PubMed1982

Synthesis and androgen effects of 7 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one, 5 alpha-androstan-3 alpha,7 alpha,17 beta-triol and 5 alpha-androstane-3 beta,7 alpha,17 beta-triol.

The steroids 7 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (7 alpha-hydroxy-Dht), 5 alpha-androstan-3 alpha,7 alpha,17 beta-triol (7 alpha-hydroxy-3 alpha-A'DIOL) and 5 alpha-androstane-3 beta,7 alpha,17 beta-triol (7 alpha-hydroxy-3 beta-A'DIOL) have been synthetized from 7 alpha,17 beta-dihydroxy-4-androsten-3-one (7 alpha-hydroxy-testosterone). The effect of administering 7 alpha-hydroxy-Dht, 7 alpha-hydroxy-3 alpha-A'DIOL or 7 alpha-hydroxy-3 beta-A'DIOL on serum levels of LH, FSH and on ventral prostate and seminal vesicle weight were investigated in gonadectomized adult male rats. Each steroid was administered for seven days in a dose of 300 micrograms per day. No suppression of serum LH or FSH levels was recorded following injections of these 7 alpha-hydroxylated steroids to castrated rats, compared to castrated control rats receiving vehicle only. Administration of 7 alpha-hydroxy-Dht or 7 alpha-hydroxy-3 alpha-A'DIOL to castrated mature rats could maintain ventral prostate and seminal vesicle weights above that of castrated control rats. Administration of 7 alpha-hydroxy-3 beta-A'DIOL to castrated mature rats resulted in ventral prostate weights slightly above castrate control levels, while seminal vesicle weight in such rats were in the same range as castrated control rats. Intraperitoneal administration of testosterone or of 5 alpha-androstane-3 beta,17 beta-diol (3 beta-A'DIOL) to castrated rats maintained activity of the androgen dependent isoenzyme of acid phosphatase in the ventral prostate; 7 alpha-hydroxy-testosterone or 7 alpha-hydroxy-3 beta-A'DIOL showed, however, no effect on this enzymic activity.

Androstane-3,17-diol↗
PubMed1982

C-19-steroid 7 alpha-hydroxylation by rat testes. Isolation and identification of: 7 alpha, 17 beta-dihydroxy-5 alpha-androstan-3-one, 5 alpha-androstan-3 alpha, 7 alpha, 17 beta-triol and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol.

From incubations of testosterone with rat testicular homogenates in the presence of a NADPH-generating system, the following 7 alpha-hydroxylated metabolites could be isolated and identified: 7 alpha, 17 beta-dihydroxy-4-androsten-3-one (7 alpha-hydroxy-testosterone), 7 alpha-17 beta-dihydroxy-5 alpha-androstan-3-one (7 alpha-hydroxy-Dht), 5 alpha-androstan-3 alpha, 7 alpha, 17 beta-triol (7 alpha-hydroxy-3 alpha-A'DIOL) and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol (7 alpha-hydroxy-3 beta-A'DIOL). To our knowledge this is the first demonstration of the formation of 5 alpha-reduced-7 alpha-hydroxylated metabolites of testosterone in the male gonad. These 5 alpha-reduced-7 alpha-hydroxylated metabolites could also be isolated after incubations of 5 alpha-androstane-3 alpha, 17 beta-diol (3 alpha-A'DIOL) with testicular homogenates in the presence of A NADPH-generating system. Measured as the sum of 7 alpha-hydroxy-testosterone, 7 alpha-hydroxy-Dht. 7 alpha-hydroxy-3 alpha-A'DIOL and 7 alpha-hydroxy-3 beta-A'DIOL formed using testosterone as substrate, total 7 alpha-hydroxylase activity was six times higher in testes of mature rats than in testes from animals 23 days old. With 3 alpha-A'DIOL as substrate total 7 alpha-hydroxylase in the mature testis was about three times greater than in the sexually immature testis.

Androstane-3,17-diol↗
PubMed1975

Simultaneous determination of testosterone, 5alpha-androstan-17beta-ol-3-one, 5alpha-androstane-3alpha,17beta-diol and 5alpha-androstane-3beta,17beta-diol in plasma of adult male rabbits by radioimmunoassay(1).

A simultaneous radioimmunoassay procedure for plasma testosterone (T), 5alpha-androstan-17beta-ol-3-one (DHT), 5alpha-androstane-3alpha,17beta-diol (3alphaol), and 5alpha-androstan-3beta,17beta-diol (3betaol) is described in this report. Peripheral plasma concentrations of T, DHT, 3alphaol, and 3betaol were 1.16 +/- 0.26, 0.49 +/- 0.15, 0.17 +/- 0.03, and 0.24 +/- 0.04 ng/ml, respectively, in adult male rabbits. In contrast, T, DHT, 3alphaol, and 3betaol peripheral plasma concentrations in dexamethasone-treated castrate rabbits were 0.07 +/- 0.01, 0.02 +/- 0.01, 0.07 +/- 0.01, and 0.05 +/- 0.01 ng/ml, respectively. These results represent the first simultaneous measurement of T, DHT, 3alphaol, and 3betaol in peripheral plasma of any male vertebrate. Moreover, we suggest that DHT, 3alphaol, and 3betaol represent the unidentified immunoreactive material found in peripheral plasma of male rabbits by Falvo and Nalbandov (1).

Androstane-3,17-diol↗
PubMed1979

Pituitary metabolism of 5alpha-androstane-3beta-17beta-diol: intense and rapid conversion into 5alpha-androstane-3beta,6alpha,17beta-triol and 5alpha-androstane-3beta,7alpha, 17beta-triol.

In the male rat pituitary, 5alpha-androstane-3beta, 17beta-diol (3beta-diol) is extensively metabolized into polar steroids. They were identified as 5alpha-androstane-3beta, 6alpha-17beta-triol (6alpha-triol) and 5alpha-androstane-3beta, 7alpha, 17beta-triol (7alpha-triol). 6-alpha-Triol represents 53% and 7alpha-Triol 28% of the total 3beta-diol metabolites. The remaining percentage is related to 6beta and 7beta isomers. The biological role of triols is still unknown.

Androstane-3,17-diol↗
PubMed1975

Formation and secretion of 5alpha-androstan-17beta-ol-3-one, 5alpha-androstan-3alpha,17beta-diol and 5alpha-androstan-3beta,17beta-diol by the perfused rabbit testis epididymis.

Rabbit testes epididymides were perfused in vitro at 36.5 C with an artificial medium containing bovine red blooc cells. Three major testosterone metabolites were formed and subsequently elaborated into the venous effluent of testes epididymibdes when testosterone-1,2,6,7-3-H was infused into the artery of the perfused organ. In contrast, testosterone-1,2,6,7-1-H remained unchanged when incubated in the artificial medium under similar conditions. Elution volume from a Sephadex LH-20 column, development in three ascending paper chromatographic (APC) systems, acetylation and development in a fourth APC system followed by gas liquid chromatography (GLC) of the acetylated products tentatively identified the radioactive-metabolites as 5alpha-androstan-17beta-ol-3-one (DHT), 5alpha-androstan-3alpha,17beta-diol (3alphaol) and 5alpha-androstan-3beta,17beta-diol (3beta-ol). The identity of these 5alpha-reduced testosterone metabolites was confirmed by crystallization to constant specific activity in the presence of authentic carrier steroid. These results suggest that DHT and androstanediols formed by perfused rabbit testes epididymides subsequently escape into the venous effluent.

Androstanes↗
PubMed1979

Age-related changes in conversion of 5 alpha-androstan-17 beta-ol-3-one to 5 alpha-androstane-3 alpha,17 beta-diol and 5 alpha-androstane-3 beta,17 beta-diol by rat testicular cells in vitro.

Conversion of labelled 5 alpha-androstane-17 beta-ol-3-one (DHT) by isolated testicular cells from rats of different ages was examined under saturating substrate conditions in vitro (5--10 micrograms DHT/ml in a 24 h incubation). Two detectable metabolites of DHT were produced by testicular cells in vitro. 5 alpha-androstane-3 alpha, 17 beta-diol (3 alpha-diol) and 5 alpha-androstane-3 beta, 17 beta-diol (3 beta-diol). Production of these diols during a 24 h period was linear, and the amounts formed were directly related to the cell number. The amount of 3 alpha- and 3 beta-diols formed by testicular cells of rats of different ages increased from Day 10 to Day 25, then declined. Testicular cells from rats 10 to 20 days of age converted DHT mainly to 3 alpha-diol, but thereafter 3 beta-diol was the predominant testicular metabolite of DHT.

Aging↗
PubMed1979

Metabolism and binding in vitro of 5 alpha-androstane-3 beta, 17 beta-diol and of 5 alpha-androstane-3 alpha, 17 beta-diol in cell fractions of rat ventral prostate and liver.

Rat ventral prostate and liver were investigated for the binding in vitro to particulate fractions and for the metabolism of 5 alpha-androstane-3 beta, 17 beta-diol. Comparative investigations were carried out on the metabolism of 5 alpha-androstane-3 alpha, 17 beta-diol. Preparations of the liver were investigated in order to establish the organ specificity of the method. In the prostate, the bulk of the metabolites of 5 alpha-androstane-3 beta, 17 beta-diol was present as steroids of high polarity. Of the less polar metabolites, 17 beta-hydroxy-5 alpha-androstan-3-one, 3 beta-hydroxy-5 alpha-androstan, 17-one and 5 alpha-androstane-3 alpha, 17 beta-diol were detectable. The binding of a 5 alpha-androstane-3 beta, 17 beta-diol to mitochondria and microsomes was unspecific. In the liver, among the less polar metabolites, 3 beta-hydroxy-5 alpha-androstan-17-one was the main metabolite, and the binding was unspecific. The main metabolite in the prostate homogenate of 5 alpha-androstane-3 alpha, 17 beta-diol was 17 beta-hydroxy-5 alpha-androstan-3-one. The portion of highly polar steroids was very low. The portion of unmetabolized hormone was distributed almost equally among the different cell preparations except the nuclei, in which 17 beta-hydroxy-5 alpha-androstan-3-one was higher and 5 alpha-androstane-3 alpha, 17 beta-diol was lower than in the remaining cell fractions.

Androstane-3,17-diol↗
PubMed1975

Some factors affecting testosterone, dihydrotestosterone, 5 alpha-androstan-3 alpha,17 beta-diol and 5 alpha-androstan-3 beta,17 beta-diol secretion by invitro perfused rabbit testes.

Intra-arterial infusion of testosterone-3H gave rise to tritiated dihydrotestosterone, 5 alpha-androstan-3 alpha,17 beta-diol and 5 alpha-androstan-3beta,17 beta-diol in spermatic venous effluent of the perfused rabbit testis-epididymis. Mass spectrometric measurements confirmed that these four androgens were present in spermatic venous effluent of the perfused rabbit testis-epididymis. Gas liquid chromatographic measurement showed that testosterone, dihydrotestosterone, 5 alpha-androstan-3 alpha,17 beta-diol and 5 alpha-androstan-3 beta,17 beta-diol were secreted in similar amounts by the in vitro perfused and in situ rabbit testis-epididymis results obtained by perfusing the testis minus the epididymis suggested that the bulk of these androgens originate from the catabolism of testosterone within the testis rather than the epididymis. Suprisingly, germinal epithelium destruction by heat failed to alter the testosterone, dihydrotestosterone and 5 alpha-androstan-3 alpha,17 beta-diol secretion by the in vitro perfused rabbit testis. In contrast, the secretion of 5 alpha-androstan-3 beta,17 beta-diol was significantly (P less than 0.05) reduced in the same cryptorchid compared to control testes.

Androstane-3,17-diol↗
PubMed1982

In vitro metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol by the rat intestine.

The metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol by the 800 g supernatant fraction by different parts of the gastrointestinal tract from male rats was investigated. This metabolism tended to be higher in immature than in mature animals. Administration of dexamethasone or long-acting ACTH to immature and mature rats increased testosterone metabolism to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol by ileum tissue. No such effect could be observed following administration of progesterone, estradiol, prolactin, LH or FSH in mature animals. Development of the gastrointestinal tract from the immature to the mature stage was associated with augmented metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol in the ileum.

Adrenocorticotropic Hormone↗
PubMed1983

Metabolism in vitro of testosterone (T) to 17 beta-hydroxy-5 alpha-androstane-3-one (DHT) and 5 alpha-androstane-3 alpha,17 beta-diol (3 alpha) by the 800 g supernatant fraction of ileum from rats.

The 800 g supernatant fraction of ileum from rats was incubated with testosterone and production of 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha,17 beta-diol measured. No difference in this production could be determined between ileum from mature female and mature male animals. Ileum from immature rats staying with their mothers from day 12 to day 21 showed increased 5 alpha-reduction of testosterone on days 15, 17 and 21. Ileal metabolism to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha,17 beta-diol was increased in immature animals on day 25 of extrauterine life when consuming rat chow and water ad libitum from day 21. This increase could not be demonstrated on day 28. Immature and mature animals treated either with long-acting ACTH or dexamethasone showed increased ileal conversion of testosterone to the two 5 alpha-reduced metabolites determined. Ileum from mature male rats injected, subcutaneously, with arabinosylcytosine every 8th h for 2 days exhibited increased metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha,17 beta-diol from the 1st to the 6th day after the last injection of arabinosylcytosine. Different aspects of intestinal metabolism of testosterone are discussed.

Androstane-3,17-diol↗
PubMed1984

Metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol in alveolar macrophages from rat lung.

5 alpha-Reduction of testosterone was observed in lung cells obtained by bronchoalveolar lavage (greater than 95% macrophages) from the rats. This activity was inhibited by progesterone and corticosterone. Production of 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol from testosterone was higher in rat pulmonary alveolar macrophages than by the 800 g supernatant fraction of whole lung homogenate from the same animals. Alveolar macrophages from rats treated with the 5 alpha-reductase inhibitor 17 beta-N,N-diethylcarbamoyl-4-aza-4-methyl-5 alpha-androstane-3-one (5 mg/100 g b.w., s.c.) showed decreased metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol 4 h after treatment. This metabolism was also decreased in alveolar macrophages from rats exposed to potassium dichromate by intratracheal instillation. When bovine alveolar macrophages were incubated with potassium dichromate, 5 alpha-reduction of testosterone decreased significantly. The function of steroid 5 alpha-reduction in alveolar macrophages is currently not known.

Androstane-3,17-diol↗
PubMed1981

Unconjugated 5 alpha-androstan-3 alpha, 17 beta-diol and 5 alpha-androstane-3 beta, 17 beta-diol in human plasma as measured by radioimmunoassay without chromatography.

A radioimmunoassay (RIA) without chromatography for the determination of 5 alpha-androstan-3 alpha, 17 beta-diol and of 5 alpha-androstane-3 beta, 17 beta-diol in human plasma by using highly specific antisera against the 15 beta-carboxyethylmercapto-bovine serum albumin conjugates is described. It could be shown that the 13% cross reaction of the 5 alpha-androstane-3 beta, 17 beta-diol antiserum with pure androst-5-ene-3 beta, 17 beta-diol was negligibly low in plasma extracts. Sensitivity, accuracy, precision, and linearity revealed results which comply with the requisites of a reliable RIA. The plasma levels obtained were as follows (mean +/- SD): 5 alpha-androstan-3 alpha, 17 beta-diol: Normal males (N = 27) 0.86 +/- 0.22 nmol/l; normal females (N = 10) 0.31 +/- 0.07 nmol/l; hirsute females (N = 25) 0.60 +/- 0.24 nmol/l; 5 alpha-androstane-3 beta, 17 beta-diol: Normal males 1.47 +/- 0.43 nmol/l; normal females 0.49 +/- 0.10 nmol/l; hirsute females 0.91 +/- 0.32 nmol/l.

Androstane-3,17-diol↗
PubMed1977

Synthesis of new steroid haptens for radioimmunoassay. Part III. 15beta-Carboxyethylmercaptosteroid-bovine serum albumin conjugates. Specific antisera for radioimmunoassay of 5alpha-dihydrotestosterone, 5alpha-androstane-3beta, 17beta-diol and 5alpha-androstane-3alpha, 17beta-diol.

The syntheses of 15beta-carboxyethylmercapto-5alpha-dihydrotestosterone, 15beta-carbosyethylmercapto-5alpha-androstane-3beta, 17beta-diol and 15beta-carboxyethylmercapto-5alpha-androstane-3alpha, 17beta-diol and the preparation of their bovine serum albumin (BSA) conjugates are described. These conjugates were employed for the generation of specific antisera suitable for radioimmunoassay (RIA) of 5alpha-dihydrotestosterone (5alpha-DHT), 5alpha-androstane-3beta, 17beta-diol (3beta-diol) and 5alpha-androstane-3alpha, 17beta-diol (3alpha-diol).

Androstane-3,17-diol↗
PubMed1979

[Evidence of 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol and of 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol in the anterior pituitary of the prepuberal male rate].

Incubation of 3H-5 alpha-androstane-3 beta, 17 beta-diol with anterior pituitaries from immature male Rats led to the major production of polar radio-metabolites. Of these, 53 and 27% were identified with 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol, respectively. The formation of these trihydroxysteroids may be involved in the intracellular regulation of 5 alpha-androstane-3 beta, 17 beta-diol levels.

Androstane-3,17-diol↗