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Triparanol
Triparanol (, ; brand name and development code MER/29, as well as many other brand names) was the first synthetic cholesterol-lowering drug. It was patented in 1959 and introduced in the United States in 1960. The developmental code name of triparanol, MER/29, became so well known that it became the registered trade name of the drug. It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching, peeling, and "fish-scale" texture), and accelerated atherosclerosis. It is now considered to be obsolete. The drug acts by inhibiting 24-dehydrocholesterol reductase, which catalyzes the final step of cholesterol biosynthesis, the conversion of desmosterol into cholesterol. Although effective in reducing cholesterol levels, this results in tissue accumulation of desmosterol, which in turn is responsible for the side effects of triparanol. Unlike statins, triparanol d ...
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Cataracts
A cataract is a cloudy area in the lens of the eye that leads to a decrease in vision. Cataracts often develop slowly and can affect one or both eyes. Symptoms may include faded colors, blurry or double vision, halos around light, trouble with bright lights, and trouble seeing at night. This may result in trouble driving, reading, or recognizing faces. Poor vision caused by cataracts may also result in an increased risk of falling and depression. Cataracts cause 51% of all cases of blindness and 33% of visual impairment worldwide. Cataracts are most commonly due to aging but may also occur due to trauma or radiation exposure, be present from birth, or occur following eye surgery for other problems. Risk factors include diabetes, longstanding use of corticosteroid medication, smoking tobacco, prolonged exposure to sunlight, and alcohol. The underlying mechanism involves accumulation of clumps of protein or yellow-brown pigment in the lens that reduces transmission of ...
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Desmosterol
Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. 24-dehydrocholesterol reductase catalyses the reduction of desmosterol to cholesterol. It is accumulated in desmosterolosis. In 2014, it was named the Molecule of the Year 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (ISMCBBPR). See also * Triparanol Triparanol (, ; brand name and development code MER/29, as well as many other brand names) was the first synthetic cholesterol-lowering drug. It was patented in 1959 and introduced in the United States in 1960. The developmental code name of trip ... References Cholestanes {{steroid-stub ...
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Withdrawn Drug
Drugs or medicines may be withdrawn from commercial markets because of risks to patients, but also because of commercial reasons (e.g. lack of demand and relatively high production costs). Where risks or harms is the reason for withdrawal, this will usually have been prompted by unexpected adverse effects that were not detected during Phase III clinical trials, i.e. they were only made apparent from postmarketing surveillance data collected from the wider community over longer periods of time. This list is not limited to drugs that were ever approved by the FDA. Some of them (lumiracoxib, rimonabant, tolrestat, ximelagatran and ximelidine, for example) were approved to be marketed in Europe but had not yet been approved for marketing in the US, when side effects became clear and their developers pulled them from the market. Some drugs in this list (e.g. LSD) were never approved for marketing in the US or Europe. Significant withdrawals Withdrawn clinical trial drugs *RG7795, i ...
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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. Livin ...
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Ethamoxytriphetol
Ethamoxytriphetol (developmental code name MER-25) is a synthetic nonsteroidal antiestrogen that was studied clinically in the late 1950s and early 1960s but was never marketed. MER-25 was first reported in 1958, and was the first antiestrogen to be discovered. It has been described as "essentially devoid of estrogenic activity" and as having "very low estrogenic activity in all species tested". However, some estrogenic effects in the uterus have been observed, so it is not a pure antiestrogen (that is, a silent antagonist of the estrogen receptor (ER)) but is, instead, technically a selective estrogen receptor modulator (SERM). For all intents and purposes, it is a nearly pure antiestrogen, however. MER-25 produces antifertility effects in animals, and garnered interest as a potential hormonal contraceptive. However, clinical development was discontinued due to its low potency and the incidence of unacceptable central nervous system side effects, including hallucinations ...
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Antiestrogen
Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like estradiol from mediating their biological effects in the body. They act by blocking the estrogen receptor (ER) and/or inhibiting or suppressing estrogen production., Antiestrogens are one of three types of sex hormone antagonists, the others being antiandrogens and antiprogestogens. Antiestrogens are commonly used to stop steroid hormones, estrogen, from binding to the estrogen receptors leading to the decrease of estrogen levels. Decreased levels of estrogen can lead to complications in sexual development. Antiandrogens are sex hormone antagonists which are able to lower the production and the effects that testosterone can have on female bodies. Types and examples Antiestrogens include selective estrogen receptor modulators (SERMs) like tamoxifen, clomifene, and raloxifene, the ER silent antagonist and selective estrogen receptor degrader (SERD) ...
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Triphenylethylene
Triphenylethylene (TPE) is a simple aromatic hydrocarbon that possesses weak estrogenic activity. Its estrogenic effects were discovered in 1937. TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens. TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands. It includes the estrogens chlorotrianisene, desmethylchlorotrianisene, estrobin (DBE), M2613, triphenylbromoethylene, triphenylchloroethylene, triphenyliodoethylene, triphenylmethylethylene; the selective estrogen receptor modulators (SERMs) afimoxifene, brilanestrant, broparestrol, clomifene, clomifenoxide, droloxifene, endoxifen, etacstil, fispemifene, idoxifene, miproxifene, miproxifene phosphate, nafoxidine, ospemifene, panomifene, and toremifene. The antiestrogen ethamoxytriphetol (MER-25) is also closely related, but is technically not a derivative of TPE and is instead ...
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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, ...
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Chlorotrianisene
Chlorotrianisene (CTA), also known as tri-''p''-anisylchloroethylene (TACE) and sold under the brand name Tace among others, is a nonsteroidal estrogen related to diethylstilbestrol (DES) which was previously used in the treatment of menopausal symptoms and estrogen deficiency in women and prostate cancer in men, among other indications, but has since been discontinued and is now no longer available. It is taken by mouth. CTA is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. It is a high- efficacy partial estrogen and shows some properties of a selective estrogen receptor modulator, with predominantly estrogenic activity but also some antiestrogenic activity. CTA itself is inactive and is a prodrug in the body. CTA was introduced for medical use in 1952. It has been marketed in the United States and Europe. However, it has since been discontinued and is no longer available in any country. Medical uses CTA has been us ...
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Triphenylethanol
Triphenylethanol, or 1,1,2-triphenylethanol, is an organic compound with a condensed structural formula of , and is related to triphenylethylene, from which it can be prepared by hydration. It is the structural analog of two drugs, the never-marketed antiestrogen ethamoxytriphetol (MER-25) and the withdrawn lipid-lowering agent triparanol, as both contain the 1,1,2-triphenylethanol moiety within their structure. There are three isomeric compounds with a "triphenylethanol" structure: * 1,1,2-triphenylethanol; * 1,2,2-triphenylethanol, with a condensed structural formula of , which exists as a pair of enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...s; and, * 2,2,2-triphenylethanol, with a condensed structural formula of . References Tertiary alcohols Phenyl c ...
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Libido
Libido (; colloquial: sex drive) is a person's overall sexual drive or desire for sexual activity. Libido is influenced by biological, psychological, and social factors. Biologically, the sex hormones and associated neurotransmitters that act upon the nucleus accumbens (primarily testosterone and dopamine, respectively) regulate libido in humans. Social factors, such as work and family, and internal psychological factors, such as personality and stress, can affect libido. Libido can also be affected by medical conditions, medications, lifestyle and relationship issues, and age (e.g., puberty). A person who has extremely frequent sexual urges, or a suddenly increased sex drive may be experiencing hypersexuality, while the opposite condition is hyposexuality. In psychoanalytic theory, libido is psychic drive or energy, particularly associated with sexual instinct, but also present in other instinctive desires and drives. A person may have a desire for sex, but not have the ...
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Gynecomastia
Gynecomastia (also spelled gynaecomastia) is the abnormal non-cancerous enlargement of one or both breasts in males due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Updated by Brent Wisse (10 November 2018) Gynecomastia can cause significant psychological distress or unease. Gynecomastia can be normal in newborn babies due to exposure to estrogen from the mother, in adolescents going through puberty, in older men over age 50, and/or in obese men. Most occurrences of gynecomastia do not require diagnostic tests. Gynecomastia may be caused by abnormal hormone changes, any condition that leads to an increase in the ratio of estrogens/androgens such as liver disease, kidney failure, thyroid disease and some non-breast tumors. Alcohol and some drugs can also cause breast enlargement. Other causes may include Klinefelter syndrome, metabolic dysfunction, or a natural decline in testosterone production. This may occur even i ...
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