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testosterone |
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CHEBI:17347 |
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An androstanoid having 17β-hydroxy and 3-oxo groups, together with unsaturation at C-4‒C-5.. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:45798, CHEBI:9461, CHEBI:15214, CHEBI:26883
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ZINC000013508431 |
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Molfile
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SDF
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js
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Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss.
Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness.
Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone.
In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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Read full article at Wikipedia
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InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 |
MUMGGOZAMZWBJJ-DYKIIFRCSA-N |
[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H] |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
Changes in the Metabolic Elimination Profile of Testosterone Following Exposure of the Crustacean Daphnia magna to TributyltinGerald A. LeBlanc and James B. McLachlanEcotoxicology and Environmental Safety 45, 296-303 (2000)
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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View more via ChEBI Ontology
17β-hydroxyandrost-4-en-3-one
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testosterona
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ChemIDplus
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testosterone
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ChemIDplus
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testosteronum
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ChemIDplus
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17beta-hydroxy-4-androsten-3-one
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ChEBI
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17beta-Hydroxy-4-androsten-3-one
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KEGG COMPOUND
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4-androsten-17β-ol-3-one
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NIST Chemistry WebBook
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Androderm
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ChemIDplus
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Testosteron
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ChemIDplus
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Testosterone
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KEGG COMPOUND
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TESTOSTERONE
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PDBeChem
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testosterone
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UniProt
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2607
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DrugCentral
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C00003675
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KNApSAcK
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C00535
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KEGG COMPOUND
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D00075
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KEGG DRUG
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DB00624
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DrugBank
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HMDB0000234
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HMDB
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LMST02020002
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LIPID MAPS
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TES
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PDBeChem
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Testosterone
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Wikipedia
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View more database links |
1915399
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Reaxys Registry Number
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Reaxys
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3653705
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Beilstein Registry Number
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Beilstein
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538843
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Gmelin Registry Number
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Gmelin
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58-22-0
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CAS Registry Number
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ChemIDplus
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58-22-0
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CAS Registry Number
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NIST Chemistry WebBook
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Hadeed NN, Thanoon IA, Al-Mukhtar SB (2014) Total testosterone levels and the effect of sildenafil on type 2 diabetics with erectile dysfunction. Oman medical journal 29, 46-50 [PubMed:24498482] [show Abstract]
ObjectivesHypotestosteronemia has been reported in approximately half of type 2 diabetic men in general. This study aims to assess serum total testosterone levels in type 2 diabetics with erectile dysfunction and to correlate the degree of improvement between sildenafil citrate and testosterone levels.MethodsA cross sectional and prospective comparative interventional study was conducted at the Diabetic Clinic of Assalam Teaching Hospital in Mosul, during the period from January 1, 2009 through to December 31, 2011. The study enrolled 120 type 2 diabetic males with erectile dysfunction who were analyzed with regard to age, duration of diabetes, duration and severity of erectile dysfunction, serum total testosteron levels and the degree of response to sildenafil citrate in terms of testosterone levels. The data were statistically analyzed using the independent two-sample Student t test, χ (2) test and Pearson correlation test. A p-value of <0.05 was considered statistically significant.ResultsThirty six percent of type 2 diabetic males with erectile dysfunction were found to have low serum testosterone levels. The hypotestosteronemic and normotestosteronemic subgroups were not significantly different in terms of mean age, duration of diabetes, reduction of libido, and reduction in erectile function. The rate and the degree of improvement of erection by sildenafil in the normo-and-hypotestosteronemic respondents were not significantly different, but the degree of improvement by sildenafil was significantly correlated to testosterone levels among the hypotestosteronemic group.ConclusionHypotestosteronemia was found in 36% of type 2 diabetic males with erectile dysfunction. The degree of improvement of erectile dysfunction by sildenafil was directly proportional to the serum testosterone levels among the hypotestosteronemic group. Therapeutic supplement with testosterone preparation in the hypotestosteronemic diabetics with erectile dysfunction may improve their response to sildenafil. | Howell S, Shalet S (2001) Testosterone deficiency and replacement. Hormone research 56 Suppl 1, 86-92 [PubMed:11786693] [show Abstract] In the human male, testosterone is the major circulating androgen. More than 95% of circulating testosterone is secreted by the testis with a production rate of 6-7 mg/day. The clinical effects of androgens are numerous, and testosterone deficiency is associated with a number of clinical abnormalities. Overt hypogonadism results in reductions in bone mineral density, alterations in body composition and effects on mood, aggressive behaviour, cognitive function, sexual function and several factors important for cardiovascular risk. Androgen replacement in this context is clearly beneficial, and numerous studies have demonstrated improvements in bone and muscle mass, reductions in body fat, and positive effects on quality of life following treatment. The benefits of therapy in men with milder degrees of hypogonadism, and elderly men with "physiological" testosterone deficiency, are less clear-cut, and the appropriate biochemical cut-off below which replacement should be offered has not been clearly defined. Several options are available for androgen replacement in adult men. Oral testosterone, intramuscular injections, subcutaneous implants and transdermal therapy have all been used. Each mode of delivery has advantages and drawbacks and the choice between them will often depend on patient reference. Recent advances include the development of longer-acting intramuscular preparations, which offer more stable androgen levels with fairly infrequent injections, and testosterone gel which appears to provide transdermal replacement without a high incidence of skin reactions. This article will examine the evidence concerning the impact of male hypogonadism and the response to androgen therapy. The question of who to treat will be addressed with particular reference to mild hypogonadism and hypogonadism in the elderly. Finally, an overview of the different modes of replacement therapy will be presented. | Ball WJ, Kasturi R, Dey P, Tabet M, O'Donnell S, Hudson D, Fishwild D (1999) Isolation and characterization of human monoclonal antibodies to digoxin. Journal of immunology (Baltimore, Md. : 1950) 163, 2291-2298 [PubMed:10438974] [show Abstract] Fab preparations of sheep polyclonal anti-digoxin Abs have proven useful for reversal of the toxic effects of digoxin overdoses in patients. Unfortunately, the use of foreign species proteins in humans is limited because of the potential for immunological responses that include hypersensitivity reactions and acute anaphylaxis. Immunization of recently developed transgenic mice, whose endogenous micro heavy and kappa light chain Ig genes are inactivated and which carry human Ig gene segments, with a digoxin-protein conjugate has enabled us to generate and isolate eight hybridoma cell lines secreting human sequence anti-digoxin mAbs. Six of the mAbs have been partially characterized and shown to have high specificity and low nanomolar affinities for digoxin. In addition, detailed competition binding studies performed with three of these mAbs have shown them to have distinct differences in their digoxin binding, and that all three structural moieties of the drug, the primary digitoxose sugar, steroid, and five-member unsaturated lactone ring, contribute to Ab recognition. | McGAVACK TH (1947) Hormones and the aging process; testosterone. New York medicine 3, 15-18 [PubMed:18900503] |
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