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Acta Medica Scandinavica Sep 1966
Topics: Androsterone; Carbon Isotopes; Etiocholanolone; Humans; Hyperthyroidism; Hypothyroidism; Myxedema; Radionuclide Imaging
PubMed: 5920076
DOI: 10.1111/j.0954-6820.1966.tb02839.x -
Steroids Sep 1968
Topics: Androsterone; Ascorbic Acid; Chemical Phenomena; Chemistry; Chromatography, Paper; Countercurrent Distribution; Electrophoresis; Sulfates; Sulfur Isotopes
PubMed: 5674523
DOI: 10.1016/0039-128x(68)90024-x -
Steroids May 2011New analogues of androgens that had never been available as approved drugs are marketed as "dietary supplement" recently. They are mainly advertised to promote muscle...
New analogues of androgens that had never been available as approved drugs are marketed as "dietary supplement" recently. They are mainly advertised to promote muscle mass and are considered by the governmental authorities in various countries, as well as by the World Anti-doping Agency for sport, as being pharmacologically and/or chemically related to anabolic steroids. In the present study, we report the detection of a steroid in a product seized by the State Bureau of Criminal Investigation Schleswig-Holstein, Germany. The product "1-Androsterone" of the brand name "Advanced Muscle Science" was labeled to contain 100mg of "1-Androstene-3b-ol,17-one" per capsule. The product was analyzed underivatized and as bis-TMS derivative by GC-MS. The steroid was identified by comparison with chemically synthesized 3β-hydroxy-5α-androst-1-en-17-one, prepared by reduction of 5α-androst-1-ene-3,17-dione with LS-Selectride (Lithium tris-isoamylborohydride), and by nuclear magnetic resonance. Semi-quantitation revealed an amount of 3β-hydroxy-5α-androst-1-en-17-one in the capsules as labeled. Following oral administration to a male volunteer, the main urinary metabolites were monitored. 1-Testosterone (17β-hydroxy-5α-androst-1-en-3-one), 1-androstenedione (5α-androst-1-ene-3,17-dione), 3α-hydroxy-5α-androst-1-en-17-one, 5α-androst-1-ene-3α,17β-diol, and 5α-androst-1-ene-3β,17β-diol were detected besides the parent compound and two more metabolites (up to now not finally identified but most likely C-18 and C-19 hydroxylated 5α-androst-1-ene-3,17-diones). Additionally, common steroids of the urinary steroid profile were altered after the administration of "1-Androsterone". Especially the ratios of androsterone/etiocholanolone and 5α-/5β-androstane-3α,17β-diol and the concentration of 5α-dihydrotestosterone were influenced. 3α-Hydroxy-5α-androst-1-en-17-one appears to be suitable for the long-term detection of the steroid (ab-)use, as this characteristic metabolite was detectable in screening up to nine days after a single administration of one capsule.
Topics: Aged; Anabolic Agents; Androstane-3,17-diol; Androsterone; Dietary Supplements; Dihydrotestosterone; Etiocholanolone; Humans; Male; Substance Abuse Detection; Testosterone
PubMed: 21310167
DOI: 10.1016/j.steroids.2011.02.001 -
Pharmacological Reports : PR 2009It is believed that a deficiency of androgens, including free testosterone, may promote the development of convulsions. The present study revealed differences in the...
It is believed that a deficiency of androgens, including free testosterone, may promote the development of convulsions. The present study revealed differences in the action of androsterone (AND), a major excreted metabolite of testosterone and a neurosteroid, in three commonly used seizure models in mice. AND administered intraperitoneally exhibited dose-dependent protection against tonic-clonic convulsions caused by maximal electroshock (MES) with ED(50) (effective dose(50)) of 227 mg/kg. The compound also inhibited the convulsive action of pentylenetetrazole (PTZ), increasing its CD(50) (convulsive dose(50)) for clonic convulsions from 77.2 (PTZ + saline) to 93.9 (p < 0.05) for PTZ + AND 40 mg/kg and 113.9 mg/kg (p < 0.001) for PTZ + AND 60 mg/kg. In mice pretreated with 60 mg/kg AND, the CD(50) for PTZ-induced tonic convulsions increased from 102 to 127.6 mg/kg (p < 0.01). Surprisingly, doses of 50 and 100 mg/kg AND lowered the CD(50) for kainate (KA)-induced convulsions from 40.8 to 28.7 (p < 0.05) and 25.4 mg/kg (p < 0.001), respectively. In summary, for two of the mouse seizure models, our findings confirmed previous studies that demonstrated protective activity of AND. However, the potentiation of KA-induced convulsions by AND was somewhat unexpected and suggested that AND may also possess proconvulsant activity.
Topics: Androsterone; Animals; Disease Models, Animal; Dose-Response Relationship, Drug; Drug Interactions; Electroshock; Kainic Acid; Male; Mice; Pentylenetetrazole; Seizures
PubMed: 19605957
DOI: 10.1016/s1734-1140(09)70100-8 -
Steroids Jan 2011The synthesis of 7β-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3β-acetoxy-17,17-(ethylenedioxy)-5-androsten...
The synthesis of 7β-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3β-acetoxy-17,17-(ethylenedioxy)-5-androsten (1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7β-hydroxy-epiandrosterone in 63% overall yield.
Topics: Androsterone; Molecular Conformation; Stereoisomerism
PubMed: 20727907
DOI: 10.1016/j.steroids.2010.08.003 -
The Journal of Clinical Endocrinology... May 1993Increased androgen production from the ovary, adrenal or locally in skin has been implicated in the pathogenesis of acne. Recent data have provided evidence that...
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.
Topics: Acne Vulgaris; Adolescent; Adult; Androgens; Androsterone; Female; Humans; Reference Values
PubMed: 8496299
DOI: 10.1210/jcem.76.5.8496299 -
Biochemical Society Transactions Sep 1973
Topics: Androstanes; Androsterone; Animals; Axilla; Dihydrotestosterone; Female; Gerbillinae; Head; Humans; Hydroxysteroids; Male; Rats; Sebaceous Glands; Skin; Stereoisomerism
PubMed: 4802629
DOI: 10.1042/bst0011119 -
Organic Letters Sep 2017A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation...
A robust and scalable route to the taccalonolide skeleton starting from trans-androsterone is presented. The synthesis features a cyclic hydroboration carbonylation reaction, which effectively establishes the trans-hydrindane DE ring junction in a remarkable annulation reaction, as well as a Claisen rearrangement and a catalytic Ullmann-type cyclization. This work is part of a larger effort to uncover new clinical candidates from the taccalonolide class of anticancer agents through advances in chemical synthesis.
Topics: Androsterone; Cyclization; Lactones; Molecular Structure; Stereoisomerism
PubMed: 28849658
DOI: 10.1021/acs.orglett.7b02349 -
Steroids Nov 1977Androsterone (3alpha-hydroxy-5alpha-androstan-17-one), 5alpha-androstane-3alpha, 17beta-diol and 5alpha-androstane-3beta, 17beta-diol were conjugated at C-16 through...
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.
Topics: Androstane-3,17-diol; Androstanes; Androsterone; Animals; Antibody Specificity; Cross Reactions; Female; Molecular Conformation; Ovary; Rabbits; Radioimmunoassay; Rats; Stereoisomerism; Tissue Extracts
PubMed: 611634
DOI: 10.1016/0039-128x(77)90057-5 -
Biochemical Pharmacology Apr 1979
Topics: Androsterone; Animals; Bile; Biotransformation; Glucuronates; Hydrolysis; Male; Rats; Tissue Distribution
PubMed: 444259
DOI: 10.1016/0006-2952(79)90298-3