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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 an ...
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Ethinylandrostenediol
Ethinylandrostenediol (developmental code name SKF-2856), also known as 17α-ethynyl-5-androstenediol, is a synthetic estrogen, progestogen, and androgen which was never marketed. It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol. Ethinylandrostenediol was first synthesized in the late 1930s and along with its close analogue ethisterone (17α-ethynyltestosterone) was one of the first progestins (synthetic progestogens) to be developed. Ethinylandrostenediol is orally active similarly to ethisterone and shows about half its progestogenic potency. Ethinylandrostenediol was an intermediate in the initial synthesis of ethisterone. Ethinylandrostenediol shows tissue selectivity in its estrogenic effects in animals and doesn't seem to have estrogenic effects in the uterus. The androgenic activity of ethinylandrostenediol is weak. An ester of ethinylandrostenediol, ethandrostate (17α-ethynyl-5-androstenediol 3β-cyclohexylpropionate), h ...
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Methandriol
Methandriol (brand names Anabol, Crestabolic, Cytobolin, Diandren, Durabolic, Madiol, Mestenediol, Methabolic, Methydiol, Sterabolic, Stenediol), also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable (as methandriol dipropionate, methandriol propionate, or methandriol bisenanthoyl acetate) formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol. Medical uses Methandriol has been used in the treatment of breast cancer in women. It has been reported to be almost as virilizing as comparable doses of testosterone propionate and methyltestosterone in women. Available forms Methandriol (brand name Androteston M, Notandron, Protandren) was previously marketed as 25 mL and 50 mg/mL aqueous suspensions for use by intramuscular injection. Chemistry Methandriol, also known as 17α-methyl-5-androste ...
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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). 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 adre ...
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Anabolic Steroid
Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolism, Anabolic Steroid, steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance. Health risks can be produced by long-term use or excessive doses of AAS. These effects include harmful changes in cholesterol levels (increased low-density lipoprotein and decreased high-density lipoprotein), acne, high blood pressure, hepatotoxicity, liver damage (mainly with most oral AAS), and left ventricular hypertrophy. These risks are further increased when athletes take steroids alongside other drugs, causing significantly more damage to their bodies. The effect of anabolic steroids on the heart can cause myocardial infarction and strokes. Conditions pertaining to hormonal imbalances such as gynecomas ...
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Dehydroepiandrosterone
Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors. In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone. Biological function As an androgen DHEA and other adrenal androgens such as androstenedione, although relatively weak androgens, are responsible for the androgenic effects of adrenarche, such as early pubic and axillary hair growth, adult-type body odor, increased ...
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Steroid
A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signal transduction, signaling molecules. Examples include the lipid cholesterol, sex hormones estradiol and testosterone, anabolic steroids, and the anti-inflammatory corticosteroid drug dexamethasone. Hundreds of steroids are found in Fungus, fungi, plants, and animals. All steroids are manufactured in cells from a sterols, sterol: Cholesterol, cholesterol (animals), lanosterol (opisthokonts), or cycloartenol (plants). All three of these molecules are produced via Cyclic compound, cyclization of the triterpene squalene. Structure The steroid nucleus (parent structure, core structure) is called gonane (cyclopentanoperhydrophenanthrene). It is typically composed of seventeen carbon atoms, bonded in fou ...
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Androgen
An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes the embryological development of the primary male sex organs, and the development of male secondary sex characteristics at puberty. Androgens are synthesized in the testes, the ovaries, and the adrenal glands. Androgens increase in both males and females during puberty. The major androgen in males is testosterone. Dihydrotestosterone (DHT) and androstenedione are of equal importance in male development. DHT ''in utero'' causes differentiation of the penis, scrotum and prostate. In adulthood, DHT contributes to balding, prostate growth, and sebaceous gland activity. Although androgens are commonly thought of only as male Sex steroids, sex hormones, females also have them, but at lower levels: they function in libido and sexual arousal. An ...
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Estrogen
Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal activity: estrone (E1), estradiol (E2), and estriol (E3). Estradiol, an estrane, is the most potent and prevalent. Another estrogen called estetrol (E4) is produced only during pregnancy. Estrogens are synthesized in all vertebrates and some insects. Quantitatively, estrogens circulate at lower levels than androgens in both men and women. While estrogen levels are significantly lower in males than in females, estrogens nevertheless have important physiological roles in males. Like all steroid hormones, estrogens readily diffuse across the cell membrane. Once inside the cell, they bind to and activate estrogen receptors (ERs) which in turn modulate the expression of many ...
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Androgen
An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes the embryological development of the primary male sex organs, and the development of male secondary sex characteristics at puberty. Androgens are synthesized in the testes, the ovaries, and the adrenal glands. Androgens increase in both males and females during puberty. The major androgen in males is testosterone. Dihydrotestosterone (DHT) and androstenedione are of equal importance in male development. DHT ''in utero'' causes differentiation of the penis, scrotum and prostate. In adulthood, DHT contributes to balding, prostate growth, and sebaceous gland activity. Although androgens are commonly thought of only as male Sex steroids, sex hormones, females also have them, but at lower levels: they function in libido and sexual arousal. An ...
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Estradiol
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy. It also has important effects in many other tissues including bone, fat, skin, liver, and the brain. Though estradiol levels in males are much lower than in females, estradiol has important roles in males as well. Apart from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species. Estradiol is produced within the follicles of the ovaries and in oth ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets). The term ''natural product'' has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized meta ...
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