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19-Norpregnane
19-Norpregnane, also known as 13β-methyl-17β-ethylgonane, is a norsteroid and the 19-demethyl analogue of pregnane. It is the parent compound of 19-norprogesterone (19-norpregn-4-ene-3,20-dione) and derivatives of it such as the progestins demegestone, gestonorone caproate (gestronol hexanoate), nomegestrol acetate, norgestomet, promegestone, segesterone acetate (nestorone), and trimegestone. See also * Gonane * Androstane * Estrane Estrane is a C18 steroid derivative, with a gonane core. ''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for i ... References Norpregnanes {{steroid-stub ...
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Gestonorone Caproate
Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and cancer of the endometrium. It is given by injection into muscle typically once a week. Side effects of gestonorone caproate include worsened glucose tolerance, decreased libido in men, and injection site reactions. Gestonorone caproate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no other important hormonal activity. Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973. It has been used widely throughout Europe, including in the United Kingdom, and has also been marketed in certain other countries such as Japan, China, and Mexico. However, it has since mostly been discontinued, and it remains availa ...
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Pregnane
Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyl etiocholane). It has a gonane core. 5β-Pregnane is the parent of pregnanediones, pregnanolones, and pregnanediols, and is found largely in urine as a metabolic product of 5β-pregnane compounds. Pregnanes Pregnanes are steroid derivatives with carbons present at positions 1 through 21. Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes. Pregnenes Pregnenes have a double bond. Examples include: * Cortisone * Hydrocortisone * Progesterone Pregnadienes Pregnadienes have two double bonds. Examples include: * Cyproterone acetate * Danazol * Fluocinonide See also * 5β-Pregnane * Pregnanedione * Pr ...
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Nomegestrol Acetate
Nomegestrol acetate (NOMAC), sold under the brand names Lutenyl and Zoely among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders.http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002068/WC500120841.pdf https://www.tga.gov.au/sites/default/files/auspar-zoely.pdf It is available both alone and in combination with an estrogen. NOMAC is taken by mouth. A birth control implant for placement under the skin was also developed but ultimately was not marketed. Side effects of NOMAC include menstrual irregularities, headaches, nausea, breast tenderness, and others. NOMAC is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some antiandrogenic activity and no other important hormonal activity. Nomegestrol, a related compound, was patented i ...
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Androstane
Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology 5α-Androstane is reported to be effective as an androgen, in spite of having no oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as we ... containing functional groups. See also * Estrane and pregnane * List of androstanes * C19H32 References {{Androgen receptor modulators Androgens and anabolic steroids Androstanes ...
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Gonane
Gonane is a chemical compound with formula , whose molecule can be described as three molecules or entities of cyclohexane and one of cyclopentane, fused in a particular way. More specifically, the molecule can be described as that of cycloheptadecane (–CH2–)17 with three extra bonds connecting carbons 1 to 13, 4 to 12, and 5 to 9, replacing six hydrogen atoms. It can also be viewed as the result of fusing a cyclopentane molecule with a fully hydrogenated molecule of phenanthrene, hence the more descriptive name perhydrocyclopenta henanthrene. Gonane is a tetracyclic hydrocarbon with no double bonds. It is formally the parent compound of the steroids; its carbon skeleton is called the "steroid nucleus". Some important gonane derivatives are the steroid hormones, characterized by methyl groups at the C10 and C13 positions and a side chain at the C17 position. Because gonane has six centers of chirality, it has 64 (26) theoretically possible stereoisomers, that differ ...
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Trimegestone
Trimegestone, sold under the brand names Ondeva and Totelle among others, is a progestin medication which is used in menopausal hormone therapy and in the prevention of postmenopausal osteoporosis. It was also under development for use in birth control pills to prevent pregnancy, but ultimately was not marketed for this purpose. The medication is available alone or in combination with an estrogen. It is taken by mouth. Side effects of trimegestone include headache, breast tenderness, nervousness, abdominal pain, bloating, muscle cramps, nausea, depression, and vaginal bleeding among others. Trimegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak antiandrogenic and antimineralocorticoid activity and no other important hormonal activity. Trimegestone was first described in 1979 and was introduced for medical use in 2001. It is sometimes described as a "f ...
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Segesterone Acetate
Segesterone acetate (SGA), sold under the brand names Nestorone, Elcometrine, and Annovera, is a progestin medication which is used in birth control and in the treatment of endometriosis in the United States, Brazil, and other South American countries.https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209627s000lbl.pdf It is available both alone and in combination with an estrogen. It is not effective by mouth and must be given by other routes, most typically as a vaginal ring or implant that is placed into fat. Side effects of SGA are similar to those of other progestins. SGA is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some affinity for the glucocorticoid receptor and has no other important hormonal activity. SGA was developed by the Population Council and was introduced for medical use by 2000. It is under development in the United States and Europe ...
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Promegestone
Promegestone, sold under the brand name Surgestone, is a progestin medication which is used in menopausal hormone therapy and in the treatment of gynecological disorders. It is taken by mouth. Side effects of promegestone include menstrual irregularities among others. Promegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak antiandrogenic, glucocorticoid, and antimineralocorticoid activity and no other important hormonal activity. The medication is largely a prodrug of trimegestone. Promegestone was first described in 1973 and was introduced for medical use in France in 1983. It has only been marketed in a few countries, including France, Portugal, Tunisia, and Argentina. In addition to its use as a medication, promegestone has been widely used in scientific research as a radioligand of the progesterone receptor. Medical uses Promegestone is used in me ...
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Norgestomet
Norgestomet, or norgestamet, sold under the brand name Syncro-Mate B and Crestar, is a progestin medication which is used in veterinary medicine to control estrus and ovulation in cattle. Uses Veterinary Norgestomet is used in veterinary medicine. Pharmacology Pharmacodynamics Norgestomet is a progestogen. In addition to the progesterone receptor, it possesses weak (micromolar) affinity for the glucocorticoid receptor. Chemistry Norgestomet, also known as 11β-methyl-17α-acetoxy-19-norprogesterone or as 17α-hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate, is a synthetic norpregnane steroid and a derivative of progesterone Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the ma .... History Norgestomet was developed and introduced for veterinary use in the mid-1970s. Soc ...
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Norsteroid
''Norsteroids'' ( nor-, L. ''norma'', from "normal" in chemistry, indicating carbon removal) are a structural class of steroids that have had an atom or atoms (typically carbon) removed, biosynthetically or synthetically, from positions of branching off of rings or side chains (e.g., removal of methyl groups), or from within rings of the steroid ring system. For instance, 19-norsteroids (e.g., 19-norprogesterone) constitute an important class of natural and synthetic steroids derived by removal of the methyl group of the natural product progesterone; the equivalent change between testosterone and 19-nortestosterone (nandrolone) is illustrated below. Examples Norsteroid examples include: 19-norpregnane (from pregnane), desogestrel, ethylestrenol, etynodiol diacetate, ethinylestradiol, gestrinone, levonorgestrel, norethisterone (norethindrone), norgestrel, norpregnatriene (from pregnatriene), quinestrol, 19-norprogesterone (from a progesterone), Nomegestrol acetate, 19 ...
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Demethyl
In chemical nomenclature, nor- is a prefix to name a structural analog that can be derived from a parent compound by the removal of one carbon atom along with the accompanying hydrogen atoms. The nor-compound can be derived by removal of a , , or CH group, or of a C atom. The "nor-" prefix also includes the elimination of a methylene bridge in a cyclic parent compound, followed by ring contraction. (The prefix "homo-" which indicates the next higher member in a homologous series, is usually limited to noncyclic carbons). ''"Since that time the meaning of the prefix has been generalized to denote the replacement of one or more methyl groups by H, or the disappearance of CH2 from a carbon chain"''. At present, the meaning is restricted to denote the removal of only one group from the parent structure, rather than the completely demethylated form of the parent compound. In literature, "nor" is sometimes called the "next lower homologue", although in this context Homology (chemist ...
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Demegestone
Demegestone, sold under the brand name Lutionex, is a progestin medication which was previously used to treat luteal insufficiency but is now no longer marketed.http://www.micromedexsolutions.com/micromedex2/ It is taken by mouth. Demegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no androgenic activity. Demegestone was first described in 1966 and was introduced for medical use in France in 1974. It has only been marketed in France, and has since been discontinued in this country. Medical uses Demegestone has been used to treat luteal insufficiency. It has also been studied in combination with estrogens, such as moxestrol, as an oral contraceptive and treatment for infertility.Hamada H, Nagao H, Toyoda H, Hayashi H, Akihiro L, & Kotaki S (1970). linical observation on oral contraceptive effect by R-2453 (Abstracts of Papers Presented at Showa 44 in the ...
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