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Allenolic Acid
Allenolic acid, or allenoic acid, is a synthetic, nonsteroidal estrogen discovered in 1947 or 1948 that, although studied clinically, was never marketed. It is an open-ring or seco- analogue of steroidal estrogens like estrone and equilenin. The compound was named after Edgar Allen, one of the pioneers in estrogen research. Although described as an estrogen, allenolic acid probably is totally inactive at the receptor, whereas a derivative, allenestrol (α,α-dimethyl-β-ethylallenolic acid), is reported to be a potent estrogen. Another derivative of allenolic acid (specifically 6-methoxy-allenestrol), methallenestril (brand name Vallestril), is also a potent estrogen and, in contrast to allenolic acid and allenestrol, has been marketed. See also * Bisdehydrodoisynolic acid * Doisynoestrol Doisynoestrol (brand names Fenocyclin, Surestrine, Surestryl; former developmental code name RS-2874), also known as fenocycline, as well as ''cis''-bisdehydrodoisynolic acid 7-methyl eth ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Liv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nonsteroidal
A nonsteroidal compound is a drug that is not a steroid nor a steroid derivative. Nonsteroidal anti-inflammatory drugs (NSAIDs) are distinguished from corticosteroids as a class of anti-inflammatory agents. List of nonsteroidal steroid receptor modulators Examples include the following: * Estrogens: benzestrol, bifluranol, estrobin (DBE), diethylstilbestrol (stilbestrol), dienestrol, erteberel, fosfestrol, hexestrol (dihydroxystilbestrol), methallenestril, methestrol, methestrol dipropionate, paroxypropione, prinaberel, and triphenylethylene, as well as many xenoestrogens * : acolbifene, afimoxifene, arzoxifene, bazedoxifene, broparestrol, chlorotrianisene, clomifene, clomifenoxide, cyclofenil, droloxifene, enclomifene, endoxifen, ethamoxytriphetol, fispemifene, idoxifene, lasofoxifene, levormeloxifene, miproxifene, nafoxidine, nitromifene, ormeloxifene, ospemifene, panomifene, pipendoxifene, raloxifene, tamoxifen, toremifene, trioxifene, zindoxifene, z ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Estrogen
Estrogen or oestrogen 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. Their presence in both vertebrates and insects suggests that estrogenic sex hormones have an ancient evolutionary history. 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 recepto ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Structural Analog
A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced with other atoms, groups, or substructures. A structural analog can be imagined to be formed, at least theoretically, from the other compound. Structural analogs are often isoelectronic. Despite a high chemical similarity, structural analogs are not necessarily functional analogs and can have very different physical, chemical, biochemical, or pharmacological properties. In drug discovery, either a large series of structural analogs of an initial lead compound are created and tested as part of a structure–activity relationship study or a database is screened for structural analogs of a lead compound. Chemical analogues of i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol ( opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholesta ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Estrone
Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estriol. Estrone, as well as the other estrogens, are synthesized from cholesterol and secreted mainly from the gonads, though they can also be formed from adrenal androgens in adipose tissue. Relative to estradiol, both estrone and estriol have far weaker activity as estrogens. Estrone can be converted into estradiol, and serves mainly as a precursor or metabolic intermediate of estradiol. It is both a precursor and metabolite of estradiol. In addition to its role as a natural hormone, estrone has been used as a medication, for instance in menopausal hormone therapy; for information on estrone as a medication, see the estrone (medication) article. Biological activity Estrone is an estrogen, specifically an agonist of the estrogen receptors ERα and ERβ. It is a far less potent estrogen than i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Equilenin
Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares. It is used as one of the components in conjugated estrogens (brand name Premarin). It was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds. Chemistry Synthesis Total synthesis The synthesis developed by the Bachmann group started from Butenand's ketone – the 7-methoxy structural analog of 1,2,3,4-tetrahydrophenanthren-1-one – and which can be readily prepared from 1,6- Cleve's acid. The approach was based on well-established transformations like the Claisen condensation, the Reformatsky reaction, the Arndt–Eistert reaction, and the Dieckmann condensation. Nicolaou described this preparation as ending the era preceding the post-World War II work of Robert Burns Woodward Robert Burns Woodward (April 10, 1917 – July ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Edgar Allen
Edgar Allen (May 2, 1892 – February 3, 1943) was an American anatomist and physiologist. He is known for the discovery of estrogen and his role in creating the field of endocrinology. Born on Cañon (Canyon) City, Colorado, Allen was educated at Brown University. After serving in World War I he took a position at Washington University in St. Louis until, in 1923, he was appointed to the chair of anatomy at the University of Missouri in Columbia, Missouri. Ten years later he was appointed to the chair at Yale University. At Missouri, he began his studies of sex hormones. While it was commonly believed at the time that the female reproductive cycle was controlled by substance in the '' corpus luteum'', Allen sought the answer in the follicles surrounding the ovum, leading to his discovery of estrogen, though it was identified six years later by Adolf Butenandt in 1929. Allen died of a heart attack in 1943 while on duty with the United States Coast Guard. References Fur ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Allenestrol
Allenestrol, or allenoestrol, also known as α,α-dimethyl-β-ethylallenolic acid or as methallenestrilphenol, is a synthetic, nonsteroidal estrogen and a derivative of allenolic acid that was never marketed. A methyl ether of allenestrol, methallenestril (methallenestrol), is also an estrogen, but, in contrast to allenestrol, has been marketed. See also * Carbestrol * Bisdehydrodoisynolic acid * Doisynolic acid Doisynolic acid is a synthetic, nonsteroidal, orally active estrogen that was never marketed. The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high ... * Doisynoestrol * Fenestrel References Carboxylic acids Naphthalenes Synthetic estrogens {{genito-urinary-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methoxy
In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as an electron-donating group, but as an electron-withdrawing group if at the ''meta'' position. At the ''ortho'' position, steric effects are likely to cause a significant alteration in the Hammett equation prediction which otherwise follows the same trend as that of the ''para'' position. Occurrence The simplest of methoxy compounds are methanol and dimethyl ether. Other methoxy ethers include anisole and vanillin. Many alkoxides contain methoxy groups, e.g. tetramethyl orthosilicate and titanium methoxide. Such compounds are often classified as methoxides. Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl. Biosynthesis In nature, methoxy groups are found on nucl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methallenestril
Methallenestril () (brand names Cur-men, Ercostrol, Geklimon, Novestrine, Vallestril), also known as methallenoestril () and as methallenestrol, as well as Horeau's acid, is a synthetic nonsteroidal estrogen and a derivative of allenolic acid and allenestrol (specifically, a methyl ether of it) that was formerly used to treat menstrual issues but is now no longer marketed. It is a seco- analogue of bisdehydrodoisynolic acid, and although methallenestril is potently estrogenic in rats, in humans it is only weakly so in comparison. Vallestril was a brand of methallenestril issued by G. D. Searle & Company in the 1950s. Methallenestril is taken by mouth. By the oral route, a dose of 25 mg methallenestril is approximately equivalent to 1 mg diethylstilbestrol, 4 mg dienestrol, 20 mg hexestrol, 25 mg estrone, 2.5 mg conjugated estrogens, and 0.05 mg ethinylestradiol. See also * Carbestrol * Fenestrel * Doisynoestrol * Doisynolic acid Doisynol ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bisdehydrodoisynolic Acid
Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ((Z)-BDDA), is a synthetic, nonsteroidal estrogen related to doisynolic acid that was never marketed. It is one of the most potent estrogens known, although it has more recently been characterized as a selective estrogen receptor modulator (SERM). BDDA and other doisynolic acid derivatives display relatively low affinity accompanied by disproportionately high estrogenic potency ''in vivo'', which was eventually determined to be due to transformation into metabolites with greater estrogenic activity. The drug was discovered in 1947 as a degradation product of the reaction of equilenin or dihydroequilenin with potassium hydroxide. It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue of estrone. These compounds, along with diethylstilbestrol, can be considered to be open-ring analogues of estradiol. The methyl ether of BDDA, doisynoestrol, is also an estrogen, and in contrast to BDDA, has been market ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
