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19-noretiocholanolone
19-Noretiocholanolone, also known as 5β-estran-3α-ol-17-one, is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone, an anabolic-androgenic steroid (AAS). Traces of 19-noretiocholanolone may be naturally present in human urine. Consumption of boar meat, liver, kidneys and heart have been found to increase urinary 19-noretiocholanolone output. See also * Etiocholanolone Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of ... * 19-Norandrosterone * 5α-Dihydronandrolone * 5α-Dihydronorethisterone References {{DEFAULTSORT:Noretiocholanolone, 19- 5α-Reduced steroid metabolites Secondary a ...
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Nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat. Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and decreased sexual desire due to its ability to suppress endogenous testosterone synthesis while not being a sufficient androgen itself. They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Nandrolone has strong anabolic effects and weak androgenic effects, which giv ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which are both p ...
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Bolandione
Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor (chemistry), precursor of the anabolic-androgenic steroid (AAS) nandrolone (19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Controlled Substances Act#Schedule III controlled substances, Schedule III drug. It is also banned from use in many sports, including the Olympic Games, under the World Anti-Doping Code. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen receptor dependent reporter gene expression is 10 times lower as compared to dihydrotestosterone (DHT). Scientific studies have shown that oral administration of bolandione is "a very ineffective strategy for stimulating skeletal muscle mass increases but may be associated with side effects". ''In vivo'' experim ...
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5α-reductase
5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes of 5α-reductase encoded by the genes SRD5A1, SRD5A2, and SRD5A3. 5α-Reductases catalyze the following generalized chemical reaction: :a 3-oxo-5α-steroid + acceptor a 3-oxo-Δ4-steroid + reduced acceptor Where a 3-oxo-5α-steroid and acceptor are substrates, and a corresponding 3-oxo-Δ4-steroid and the reduced acceptor are products. An instance of this generalized reaction that 5α-reductase type 2 catalyzes is: :dihydrotestosterone + NADP+ \rightleftharpoons testosterone + NADPH + H+ where dihydrotestosterone is the 3-oxo-5α-steroid, NADP+ is the acceptor and testosterone is the 3-oxo-Δ4-steroid and NADPH the reduced acceptor. Production and activity The enzyme is produced in many tissues in both males and females, in the r ...
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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 activities include scientific research, education, development of anti-doping capacities, and monitoring of the World Anti-Doping Code, whose provisions are enforced by the UNESCO International Convention Against Doping in Sport. The aims of the Council of Europe Anti-Doping Convention and the United States Anti-Doping Agency are also closely aligned with those of WADA. History The World Anti-Doping Agency is a foundation created through a collective initiative led by the International Olympic Committee (IOC). It was set up on 10 November 1999 in Lausanne, Switzerland, as a result of what was called the "Declaration of Lausanne", to promote, coordinate and monitor the fight against drugs in sports. Since 2002, the organization's head ...
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Anabolic-androgenic Steroid
Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone (medication), testosterone as well as synthetic androgens that are structurally related and have similar effects to testosterone. They increase protein within cell (biology), cells, especially in skeletal muscles, and also have varying degrees of virilization, virilizing effects, including induction of the development and maintenance of male, masculine secondary sexual characteristics such as the growth of facial hair, facial and body hair. The word ''anabolic'', referring to anabolism, comes from the Greek ἀναβολή ''anabole'', "that which is thrown up, mound". Androgens or AAS are one of three types of sex hormone agonists, the others being estrogen (medication), estrogens like estradiol (medication), estradiol and progestogens like progesterone (medication), progesterone. AAS were synthesized in the 1930s, and are ...
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Urine
Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excretion, excreted from the body through the urethra. Cell (biology), Cellular metabolism generates many by-products that are rich in nitrogen and must be clearance (medicine), cleared from the Circulatory system, bloodstream, such as urea, uric acid, and creatinine. These by-products are expelled from the body during urination, which is the primary method for excreting water-soluble chemicals from the body. A urinalysis can detect nitrogenous wastes of the mammalian body. Urine plays an important role in the earth's nitrogen cycle. In balanced ecosystems, urine fertilizes the soil and thus helps plants to grow. Therefore, Reuse of excreta, urine can be used as a fertilizer. Some animals use it to territory (animal)#Scent marking, mark their territories. Historically, aged or fermented urine (kn ...
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Etiocholanolone
Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the immune system. Etiocholanolone 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 etiocholanolone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. Etiocholanolone has been studied as a pyrogenic steroid in the so-called steroid fever (or etiocholanolone fever), a condiditon similar to familial mediterranean fever (FMF). Etiocholanolone (like pregnano ...
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5α-Dihydronandrolone
5α-Dihydronandrolone (also known as 5α-DHN, dihydronandrolone, DHN, 5α-dihydro-19-nortestosterone, or 5α-estran-17β-ol-3-one) is a naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of nandrolone (19-nortestosterone). It is a major metabolite of nandrolone and is formed from it by the actions of the enzyme 5α-reductase analogously to the formation of dihydrotestosterone (DHT) from testosterone. When testosterone is 5α-reduced into DHT, which is a much more potent AAS in comparison, its effects are potentiated on a local level. The tissues in which this occurs (i.e., the tissues that express 5α-reductase) are referred to as "androgenic" tissues and include the skin, hair follicles, and prostate gland, among others. The conversion of testosterone into DHT is an important factor in the etiology of a variety of androgen-dependent conditions, including acne, excessive facial/body hair growth, scalp hair loss, prostate enlargement, and prostat ...
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5α-Dihydronorethisterone
5α-Dihydronorethisterone (5α-DHNET, dihydronorethisterone, 17α-ethynyl-5α-dihydro-19-nortestosterone, or 17α-ethynyl-5α-estran-17β-ol-3-one) is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues. Unlike norethisterone which is purely progestogenic, 5α-DHNET has been found to possess both progestogenic and marked antiprogestogenic activity, showing a profile of progestogenic activity like that of a selective progesterone receptor modulator (SPRM). Moreover, the affinity of 5α-DHNET for the progesterone receptor (PR) is greatly reduced relative to that of norethisterone at only 25% of that of progesterone (versus 150% for norethisterone). 5α-DHNET shows higher affinity for the androgen receptor (AR) compared to norethisterone with approximately 27% of the affinity of the potent androgen ...
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