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Zeranol
Zeranol (, , ) (brand names Frideron, Ralabol, Ralgro, Ralone, Zerano; developmental code names MK-188, P-1496), or zearanol, also known as α-zearalanol or simply zearalanol, is a synthetic nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in fungi in the ''Fusarium'' genus and is used mainly as an anabolic agent in veterinary medicine. Zeranol is approved for use as a growth promoter in livestock, including beef cattle, under the brand name Ralgro (by Merck Animal Health) in the United States. In Canada, it is approved for use in beef cattle only. Its application is not approved for use in the European Union. However, it is marketed under the brand name Ralone in Spain. Although zeranol may increase cancer cell proliferation in already existing breast cancer, dietary exposure from the use of zeranol-containing implants in cattle is insignificant. Zeranol may be found as a contaminant in fungus-infected crops. It is 3 to 4 times more pote ...
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Beef Hormone Controversy
The Beef Hormone Dispute is one of the most intractable agricultural controversies since the establishment of the World Trade Organization (WTO). It has sometimes been called the "beef war" in the media, similarly to the UK–EU Beef war over the '' mad cow disease'' issue, creating some confusion, since these two wars overlapped in time. In 1989, the European Union banned the importation of meat that contained artificial beef growth hormones approved for use and administered in the United States. Originally, the ban covered six such hormones but was amended in 2003 to permanently ban one hormone —estradiol-17β — while provisionally banning the use of the five others. WTO rules permit such bans, but only where a signatory presents valid scientific evidence that the ban is a health and safety measure. Canada and the United States opposed this ban, taking the EU to the WTO Dispute Settlement Body. In 1997, the WTO Dispute Settlement Body ruled against the EU. History ...
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Mycoestrogen
Mycoestrogens are xenoestrogens produced by fungi. They are sometimes referred to as mycotoxins. Among important mycoestrogens are zearalenone, zearalenol and zearalanol. Although all of these can be produced by various ''Fusarium'' species, zearalenol and zearalanol may also be produced endogenously in ruminants that have ingested zearalenone. Alpha-zearalanol is also produced semisynthetically, for veterinary use; such use is prohibited in the European Union. Mechanism of action Mycoestrogens act as agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...s of the estrogen receptors, ERα and ERβ. Sources Mycoestrogens are produced by various strains of fungi, many of which fall under the genus ''Fusarium''. ''Fusarium'' fungi are filamentous fungi that are found in t ...
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Mycoestrogens
Mycoestrogens are xenoestrogens produced by fungi. They are sometimes referred to as mycotoxins. Among important mycoestrogens are zearalenone, zearalenol and zearalanol. Although all of these can be produced by various ''Fusarium'' species, zearalenol and zearalanol may also be produced endogenously in ruminants that have ingested zearalenone. Alpha-zearalanol is also produced semisynthetically, for veterinary use; such use is prohibited in the European Union. Mechanism of action Mycoestrogens act as agonists of the estrogen receptors, ERα and ERβ. Sources Mycoestrogens are produced by various strains of fungi, many of which fall under the genus ''Fusarium''. ''Fusarium'' fungi are filamentous fungi that are found in the soil and are associated with plants and some crops, especially cereals. Zearalenone is mainly produced by ''F. graminearum'' and ''F. culmorum'' strains, which inhabit different areas depending on temperature and humidity. ''F. graminearum'' prefers to inha ...
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Taleranol
Taleranol (INN, USAN) (developmental code name P-1560), or teranol, also known as β-zearalanol, is a synthetic, nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in '' Fusarium spp'' which was never marketed. It is the β epimer of zeranol (α-zearalanol) and is a major metabolite of zeranol but with less biological activity. See also * α-Zearalenol * β-Zearalenol * Zearalanone * Zearalenone Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some ''Fusarium'' and '' Gibberella'' species. Specifically, the ''Gibberella zeae ,'' the fungal species where zearalenone was initially detected ... References Lactones Mycoestrogens Mycotoxins Resorcinols {{genito-urinary-drug-stub ...
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Nonsteroidal Estrogen
A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used. On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES, and these drugs remain widely used in medicine for the treatment of breast cancer among other indications. In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity. Pharmacology Nonsteroidal estrogens act as agonists of the estrogen receptors, ERα an ...
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Resorcylic Acid Lactone
Resorcylic acid lactones are a group of estrogenic compounds. They are lactones of resorcylic acid. Examples include the mycoestrogens (and synthetic analogues) zearalenone, zearalanone, zeranol (α-zearalanol), taleranol Taleranol (INN, USAN) (developmental code name P-1560), or teranol, also known as β-zearalanol, is a synthetic, nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in '' Fusarium spp'' which was never mar ... (β-zearalanol), α-zearalenol, and β-zearalenol. References Dihydroxybenzoic acids Lactones Mycoestrogens {{Chemistry-stub ...
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Nonsteroidal Estrogen
A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used. On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES, and these drugs remain widely used in medicine for the treatment of breast cancer among other indications. In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity. Pharmacology Nonsteroidal estrogens act as agonists of the estrogen receptors, ERα an ...
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Oral Administration
Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are intended to have a systemic effect, reaching different parts of the body via the bloodstream, for example. Oral administration can be easier and less painful than other routes, such as injection. However, the onset of action is relatively low, and the effectiveness is reduced if it is not absorbed properly in the digestive system, or if it is broken down by digestive enzymes before it can reach the bloodstream. Some medications may cause gastrointestinal side effects, such as nausea or vomiting, when taken orally. Oral administration can also only be applied to conscious patients, and patients willing and able to swallow. Terminology ''Per os'' (; ''P.O.'') is an adverbial phrase meaning literally from Latin "through the mouth" or "by mouth ...
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Breast Cancer
Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or a red or scaly patch of skin. In those with distant spread of the disease, there may be bone pain, swollen lymph nodes, shortness of breath, or yellow skin. Risk factors for developing breast cancer include obesity, a lack of physical exercise, alcoholism, hormone replacement therapy during menopause, ionizing radiation, an early age at first menstruation, having children late in life or not at all, older age, having a prior history of breast cancer, and a family history of breast cancer. About 5–10% of cases are the result of a genetic predisposition inherited from a person's parents, including BRCA1 and BRCA2 among others. Breast cancer most commonly develops in cells from the lining of milk ducts and the lobules that supp ...
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Resorcinols
Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or ''meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide. Production Resorcinol is produced in several steps from benzene, starting with dialkylation with propylene to give 1,3-diisopropylbenzene. Oxidation and Hock rearrangement of this disubstituted arene gives acetone and resorcinol. Resorcinol is an expensive chemical, produced in only a very few locations around the world (to date only four commercial plants are known to be operative: in the United States, Germany,China and Japan), and as such it is the determining factor in the cost of PRF adhesives. Many additional routes exist for resorcinol. It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. This method ha ...
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Mycotoxins
A mycotoxin (from the Greek μύκης , "fungus" and τοξίνη , "toxin") is a toxic secondary metabolite produced by organisms of kingdom Fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually reserved for the toxic chemical products produced by fungi that readily colonize crops. Examples of mycotoxins causing human and animal illness include aflatoxin, citrinin, fumonisins, ochratoxin A, patulin, trichothecenes, zearalenone, and ergot alkaloids such as ergotamine. One mold species may produce many different mycotoxins, and several species may produce the same mycotoxin. Production Most fungi are aerobic (use oxygen) and are found almost everywhere in extremely small quantities due to the diminute size of their spores. They consume organic matter wherever humidity and temperature are sufficient. Where conditions are right, fungi proliferate into colonies and mycotoxin levels become high. The reason for the p ...
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Lactones
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the corresponding hydroxycarboxylic acids, which takes place spontaneously when the ring that is formed is five- or six-membered. Lactones with three- or four-membered rings (α-lactones and β-lactones) are very reactive, making their isolation difficult. Special methods are normally required for the laboratory synthesis of small-ring lactones as well as those that contain rings larger than six-membered. Nomenclature Lactones are usually named according to the precursor acid molecule (''aceto'' = 2 carbon atoms, ''propio'' = 3, ''butyro'' = 4, ''valero'' = 5, ''capro'' = 6, etc.), with a ''-lactone'' suffix and a Greek letter prefix that specifies the number of carbon atoms in the heterocycle — that is, the distance between the relevant -OH ...
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