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List Of Androstanes
This is a list of androstanes, or androstane derivatives. Androstanes * Androstanol ** 3α,5α-Androstanol (5α-androstan-3α-ol) – an endogenous CAR antagonist ** 3α,5β-Androstanol (5α-androstan-3β-ol) – an endogenous CAR antagonist ** 5α,17-Androstanol (5α-androstan-17-ol) – an endogenous CAR antagonist * Androstanone ** 5α-Androstanone (5α-androstan-3-one) * Androstanediol ** 3α-Androstanediol (5α-androstane-3α,17β-diol) – an endogenous androgen, estrogen, and neurosteroid ** 3β-Androstanediol (5α-androstane-3β,17β-diol) – an endogenous estrogen * Androstanedione ** 5α-Androstanedione (5α-androstane-3,17-dione) ** 5β-Androstanedione (5β-androstane-3,17-dione) * Androstanolone ** Dihydrotestosterone (5α-androstan-17β-ol-3-one) – an endogenous androgen ** 5β-Dihydrotestosterone (5β-androstan-17β-ol-3-one) ** Androsterone (5α-androstan-3α-ol-17-one) – an endogenous androgen and neurosteroid ** Epiandrosterone (5α-androstan-3β-ol-17- ...
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Androstane
Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology 5α-Androstane is reported to be effective as an androgen, in spite of having no oxygen containing functional groups. See also * Estrane and pregnane * List of androstanes This is a list of androstanes, or androstane derivatives. Androstanes * Androstanol ** 3α,5α-Androstanol (5α-androstan-3α-ol) – an endogenous CAR antagonist ** 3α,5β-Androstanol (5α-androstan-3β-ol) – an endogenous CAR antagonist ... * C19H32 References {{Androgen receptor modulators Androgens and anabolic steroids Androstanes ...
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Androsterone
Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right. Androsterone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABAA receptor, and possesses anticonvulsant effects. The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The ...
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5-Androstenedione
5-Androstenedione, also known as androst-5-ene-3,17-dione, is a prohormone of testosterone. The World Anti-Doping Agency prohibits its use in athletes. In the United States, it is a controlled substance. 5-Androstenedione is structurally similar to 4-androstenedione, with the exception of the position of a carbon-carbon double bond. 4-Androstenedione is naturally produced in the body by the adrenal glands and gonads. In addition to testosterone, it is also a precursor of estrone and estradiol. 5-Androstenedione is on the World Anti-Doping Agency The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key ...'s list of prohibited substances, and is therefore banned from use in most major sports. References External links 5-Androstenedione Androgens and anabolic steroids Androstanes ...
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4-Androstenedione
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol). Biological function Androstenedione is a precursor of testosterone and other androgens, as well as of estrogens like estrone, in the body. In addition to functioning as an endogenous prohormone, androstenedione also has weak androgenic activity in its own right. Androstenedione has been found to possess some estrogenic activity, similarly to other DHEA metabolites. However, in contrast to androstenediol, its affinity for the estrogen receptors is very low, with less than 0.01% of the affinity of estradiol for both the ERα and ERβ. Adrenarche In children aged 6 to 8 years old, there is a rise in androstenedione secretion along with DHEA during a ...
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Androstenedione
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol). Biological function Androstenedione is a precursor of testosterone and other androgens, as well as of estrogens like estrone, in the body. In addition to functioning as an endogenous prohormone, androstenedione also has weak androgenic activity in its own right. Androstenedione has been found to possess some estrogenic activity, similarly to other DHEA metabolites. However, in contrast to androstenediol, its affinity for the estrogen receptors is very low, with less than 0.01% of the affinity of estradiol for both the ERα and ERβ. Adrenarche In children aged 6 to 8 years old, there is a rise in androstenedione secretion along with DHEA during adr ...
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5-Androstenediol
Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione). Biological activity Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, DHEA. It is less androgenic than the related compound, Δ4-androstenediol, and has been found to stimulate the immune system. When administered to rats, androstenediol, ''in vivo'', has approximately 1.4% of the androgenicity of DHEA, 0.54% of the androgenicity of androstenedione, and 0.21% of the androgenicity of testosterone. Androstenediol possesses potent estrogenic activity, similarly to DHEA and 3β-androstanediol. It has approximately 6% and 17% of the affinity of estradiol at the ERα and ERβ, respectively. Although and ...
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Androstenediol
Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione). Biological activity Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, DHEA. It is less androgenic than the related compound, Δ4-androstenediol, and has been found to stimulate the immune system. When administered to rats, androstenediol, ''in vivo'', has approximately 1.4% of the androgenicity of DHEA, 0.54% of the androgenicity of androstenedione, and 0.21% of the androgenicity of testosterone. Androstenediol possesses potent estrogenic activity, similarly to DHEA and 3β-androstanediol. It has approximately 6% and 17% of the affinity of estradiol at the ERα and ERβ, respectively. Although and ...
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Androstenone
Androstenone (5α-androst-16-en-3-one) is a 16-androstene class steroidal pheromone. It is found in boar's saliva, celery cytoplasm, and truffle fungus. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when inhaled by a female pig that is in heat, results in the female assuming the mating stance. Androstenone is the active ingredient in 'Boarmate', a commercial product made by DuPont sold to pig farmers to test sows for timing of artificial insemination. Biosynthesis Androstenone is synthesized from androstadienone by 5α-reductase, and can be converted into 3α-androstenol or 3β-androstenol by 3-ketosteroid reductase. Properties Depending upon the subject, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell. There are two different genotypes that allow an individual to smell androstenone. The first genotype, which consists of two ful ...
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Androstenol
Androstenol, also known as 5α-androst-16-en-3α-ol (shortened to 3α,5α-androstenol or 3α-androstenol), is a 16-androstene class steroidal pheromone and neurosteroid in humans and other mammals, notably pigs. It possesses a characteristic musk-like odor. Androstenol, or a derivative, is found in black truffles. This was offered as an explanation for how pigs locate them deep in the ground: Androstenol is produced in the saliva of male pigs. However, experiments in France using pigs to scent truffles, truffle scent extract, and purified androstenol showed that pigs responded to the first two (actually trying to eat dirt containing the truffle extract), but ignored the androstenol. A positional isomer of androstenol, 3β-androstenol (5α-androst-16-en-3β-ol), is also endogenous to humans (as well as to pigs), behaving as a pheromone and contributing to axillary odor. Biosynthesis In humans and boars, androstenol is biosynthesized in the testes. Pregnenolone is metabolized int ...
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