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17β-hydroxy-5α-androstan-3-one |
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CHEBI:16330 |
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17beta-hydroxy-5alpha-androstan-3-one |
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A 17β-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with α-configuration at position 5. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:793, CHEBI:11342, CHEBI:41876, CHEBI:11341, CHEBI:19175
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ChemicalBook:CB9181225, eMolecules:477779, ZINC000003814360 |
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Molfile
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SDF
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more structures >>
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Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.
The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver, and brain. This enzyme mediates reduction of the C4-5 double bond of testosterone. DHT may also be synthesized from progesterone and 17α-hydroxyprogesterone via the androgen backdoor pathway in the absence of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor (AR).
In addition to its role as a natural hormone, DHT has been used as a medication, for instance in the treatment of low testosterone levels in men; for information on DHT as a medication, see the androstanolone article. |
Read full article at Wikipedia
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InChI=1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 |
NVKAWKQGWWIWPM-ABEVXSGRSA-N |
[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2 |
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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-hydroxy-5α-androstan-3-one
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androstanolona
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ChemIDplus
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androstanolone
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WHO MedNet
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androstanolone
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ChemIDplus
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androstanolonum
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ChemIDplus
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17beta-hydroxy-5alpha-androstan-3-one
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ChEBI
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17beta-Hydroxy-5alpha-androstan-3-one
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KEGG COMPOUND
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17β-hydroxy-5α-androstan-3-one
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UniProt
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17beta-hydroxyandrostan-3-one
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ChEBI
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17beta-Hydroxyandrostan-3-one
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KEGG COMPOUND
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17beta-Hydroxyandrostan-3-one
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KEGG COMPOUND
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4,5α-dihydrotestosterone
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ChEBI
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5α-DHT
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ChEBI
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5alpha-dihydrotestosterone
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ChEBI
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5alpha-Dihydrotestosterone
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KEGG COMPOUND
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Androstanolone
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KEGG COMPOUND
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DHT
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PDBeChem
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Dihydrotestosteron
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ChEBI
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DIHYDROTESTOSTERONE
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PDBeChem
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dihydrotestostérone
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ChEBI
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Stanolone
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NIST Chemistry WebBook
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521-18-6
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CAS Registry Number
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KEGG COMPOUND
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521-18-6
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CAS Registry Number
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NIST Chemistry WebBook
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521-18-6
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CAS Registry Number
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ChemIDplus
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Sakhri S, Gooren LJ (2007) Safety aspects of androgen treatment with 5alpha-dihydrotestosterone. Andrologia 39, 216-222 [PubMed:18076420] [show Abstract] 5alpha-Dihydrotestosterone (DHT), the most powerful naturally occurring androgen, is commercially available since 1982 as a gel. In view of its considerably higher biopotency (three to six times) than of testosterone, side effects, particularly on the main target organ of androgens, the prostate, are anticipated. In fact, DHT appears to be a prostate-sparing androgen for two reasons. Unlike testosterone, it does not undergo any further amplification in biopotency through 5alpha reduction in the prostate. Secondly, it is likely to lead to less aromatisation of testosterone to oestradiol in the prostate, thus reducing local oestradiol concentrations. Oestrogens have been implicated in the aetiology of benign prostate hyperplasia and prostate cancer. However, aromatisation of testosterone has appeared to be essential for the maintenance of bone mineral density. Administration of DHT reduces circulating oestradiol levels, but the levels remain above the levels critical for the antiresorptive effect of oestrogens on bone. Effects of DHT on erythropoiesis and on lipids are very similar to those of testosterone. Safety concerns regarding androgen treatment with DHT are similar to those of treatment with testosterone, while the effects of DHT on the prostate are likely to be less biopotent. | Putnam SK, Sato S, Riolo JV, Hull EM (2005) Effects of testosterone metabolites on copulation, medial preoptic dopamine, and NOS-immunoreactivity in castrated male rats. Hormones and behavior 47, 513-522 [PubMed:15811352] [show Abstract] The medial preoptic area (MPOA) is an important integrative site for male sexual behavior. Dopamine (DA) is released in the MPOA of male rats shortly before and during copulation. In a previous study, we identified 17beta-estradiol (E(2)) as the metabolite of testosterone (T) that maintains MPOA basal extracellular DA levels. However, the presence of dihydrotestosterone (DHT), an androgenic metabolite of T, is required for the female-induced increase in MPOA DA observed during copulation. Recently, we reported that assays of MPOA tissue DA content showed that castrates actually had more stored DA than did gonadally intact males. Therefore, the reduction in extracellular levels in castrates was not due to decreased availability of DA; most likely it was due to decreased release. Furthermore, T upregulates neuronal nitric oxide synthase (nNOS) in the MPOA. NO has been implicated in the regulation of DA release in the MPOA. It is not known, however, which metabolite(s) of T regulate(s) tissue stores of DA and/or nNOS in the MPOA of male rats. The present experiments were designed to test the following: (1) whether E(2), DHT, or the combination of the two influences MPOA DA tissue levels, an indication of stored DA, in male rat castrates; and (2) whether E(2), DHT, or the combination of the two influences NOS-ir in the MPOA of castrated male rats. The results indicate that E(2) up-regulates nNOS-ir in the MPOA and maintains tissue content of DA at levels similar to those in T-treated rats. DHT did not influence nNOS-ir, while attenuating the effect of castration on tissue DA content. | Edinger KL, Lee B, Frye CA (2004) Mnemonic effects of testosterone and its 5alpha-reduced metabolites in the conditioned fear and inhibitory avoidance tasks. Pharmacology, biochemistry, and behavior 78, 559-568 [PubMed:15251265] [show Abstract] Experiments were conducted to examine whether performance in hippocampally-mediated learning tasks is influenced by testosterone (T) and/or its 5alpha-reduced metabolites, dihydrotestosterone (DHT) and 3alpha-androstanediol (3alpha-diol). Performance in the conditioned fear and inhibitory avoidance tasks were examined in intact and gonadectomized (GDX), androgen-replaced rats. In Experiment 1, the behavior of intact and GDX rats in the conditioned fear paradigm were compared. GDX rats spent more time freezing, an index of increased learning, in the context, hippocampally-mediated task, but not in the cued, amygdala-mediated task. In Experiment 2, GDX rats were administered T, DHT, 3alpha-diol, estrogen (E2), or vehicle 1 mg/kg sc after training in the conditioned fear paradigm. T-, 3alpha-diol-, or E2-, compared with vehicle-administered rats, spent significantly more time freezing in the contextual, but not the cued, condition. In Experiment 3, intact compared with GDX rats had significantly longer crossover latencies, indicating better performance, in the inhibitory avoidance task. In Experiment 4, T, DHT, 3alpha-diol, or vehicle 1 mg/kg sc was administered to GDX rats immediately following training in the inhibitory avoidance task. Rats administered T, DHT, or 3alpha-diol had significantly longer crossover latencies compared with vehicle controls. In Experiment 5, androgen levels in the hippocampus were elevated 1 h following administration, when androgen exposure is essential for consolidation. These data indicate that androgens effects to enhance learning may be mediated in part by actions of 5alpha-reduced metabolites in the hippocampus. |
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