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1-testosterone

A 3-oxo Delta(4)-steroid that is estr-4-ene substituted by a beta-hydroxy group at position 17 and an alpha-methyl group at position 2." []

Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Etiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001, 13795320, 11161304, 2026727). Etiocholanedione has been found to be a metabolite of Corynebacterium (PMID: 11161304).

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.

Normethandrolone is a steroid. It has a role as an estrogen.

Testosterone is the primary male sex hormone and anabolic steroid from the androstane class of steroids. It is the most important androgen in potency and quantity for vertebrates. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. In addition, testosterone is involved in health and well-being, and the prevention of osteoporosis. Testosterone exerts its action through binding to and activation of the androgen receptor. In mammals, testosterone is metabolized mainly in the liver. Approximately 50% of testosterone is metabolized via conjugation into testosterone glucuronide and to a lesser extent testosterone sulfate by glucuronosyltransferases and sulfotransferases. An additional 40% of testosterone is metabolized in equal proportions into the 17-ketosteroids androsterone and etiocholanolone via the combined actions of 5alpha- and 5beta-reductases, 3alpha-hydroxysteroid dehydrogenase, and 17beta-HSD. Like other steroid hormones, testosterone is derived from cholesterol. The first step in the biosynthesis of testosterone involves the oxidative cleavage of the side-chain of cholesterol by the cholesterol side-chain cleavage enzyme (P450scc, CYP11A1) to give pregnenolone. In the next step, two additional carbon atoms are removed by the CYP17A1 (17alpha-hydroxylase/17,20-lyase) enzyme to yield a variety of C19 steroids. In addition, the 3beta-hydroxyl group is oxidized by 3beta-hydroxysteroid dehydrogenase to produce androstenedione. In the final and rate limiting step, the C17 keto group androstenedione is reduced by 17beta-hydroxysteroid hydrogenase to yield testosterone. Testosterone is synthesized and released by the Leydig cells in the testes that lie between the tubules and comprise less than 5% of the total testicular volume. Testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some testosterone binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. The largest amounts of testosterone (>95%) are produced by the testes in men, while the adrenal glands account for most of the remainder. Testosterone is also synthesized in far smaller total quantities in women by the adrenal glands, thecal cells of the ovaries, and, during pregnancy, by the placenta. Testosterone levels fall by about 1% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450, 17875487).

Epitestosterone, or isotestosterone, also known as 17alpha-testosterone or as androst-4-en-17alpha-ol-3-one belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. Epitestosterone is an endogenous steroid and a C-17 epimer of the androgen sex hormone testosterone. It is a weak competitive antagonist of the androgen receptor (AR) and a potent 5alpha-reductase inhibitor. Structurally, epitestosterone differs from testosterone only in the configuration at the hydroxy-bearing carbon, C17. Epitestosterone is believed to form in a similar way to testosterone with 50% of epitestosterone production in human males taking place in the testis. Epitestosterone levels are typically highest in young males; however, by adulthood, most healthy males exhibit a testosterone to epitestosterone ratio (T/E ratio) of about 1:1 (PMID: 11901061). A study of Australian athletes found that the mean T/E ratio in the study was 1.15:1. Another study found that the max T/E ratio for the 95th percentile of athletes was 3.71:1, and the max T/E ratio for the 99th percentile was 5.25:1. Epitestosterone has not been shown to enhance athletic performance, although administration of epistestosterone can be used to mask a high level of testosterone if the standard T/E ratio test is used. As such, epitestosterone is banned by many sporting authorities as a masking agent for testosterone. Interestingly, small amounts of ethanol can elevate T/E values, with women being more susceptible (PMID: 28671321).

Dehydroandrosterone is a normal human androgen. It has been found dehydroandrosterone and other androgens excretion is affected by seasonal rhythms changes. In a study of patients with peptic ulcer in the stage of remission, their androgen levels were higher both in summer and winter, but in the spring their levels are higher in normal subjects. There is a high correlation between Dehydroandrosterone excretion and testosterone; this ratio is also used as an aid for a better discrimination between physiologically high and pharmacologically high ratios of testosterone in sports. (PMID: 3157236, 9001956, 10774538).

4-Dihydroboldenone is a metabolite of boldenone. Boldenone is an androgenic anabolic steroid (AAS) intensively used for growth-promoting purposes in animals destined for meat production and as a performance enhancer in athletics. Therefore, its use is officially banned in both humans and in animals intended for human consumption. Because most anabolic steroids are completely metabolized and usually no parent steroid is excreted, metabolite identification is crucial to detect the illegal use of anabolic steroids either in humans or in livestock. Androgenic anabolic steroids are defined as natural, synthetic, or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic, and neuroendocrine systems, the AAS has been extensively used in sports activities (PMID: 2663904, 16195040, 16292586, 1663826, 16799097, 16888758, 16923823, 9249887).

alpha-Amylcinnamyl isovalerate is a flavouring ingredien

17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one is a 3-hydroxy steroid. It has a role as an androgen. 17-Hydroxyandrost-4-en-3-one is a natural product found in Punica granatum with data available. An ester of TESTOSTERONE with a propionate substitution at the 17-beta position.

Trestolone (7α-methyl-19-nortestosterone) is a synthetic androgen developed by the Population Council as a potential candidate drug for use in hormonal male contraceptive methods. In males, regular administration of sufficient quantities of trestolone induces a state of temporary infertility.