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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 a triphenyleth ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stilbestrol
Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid nonsteroidal estrogen and the parent compound of a group of more potent nonsteroidal estrogen derivatives that includes, most notably, diethylstilbestrol (DES). The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound. Stilbestrol itself is an active estrogen but is less potent than DES and other derivatives. Stilbestrol derivatives The stilbestrol estrogenic drugs include the following: * Acefluranol (an antiestrogen) * Benzestrol (''technically'' not a stilbestrol derivative due to its elongated central chain, but a very close analogue and grouped with the stilbestrol estrogens in any case) * Bifluranol * Dienestrol ** Dienestrol acetate * Diethylstilbestrol (commonly, but erroneously shortened to simply “stilbestrol”) ** Diethylstilbestrol diacetate ** Diethylstilbestrol dilaurate ** Diethylstilbestrol dipalmitate ** Die ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Panomifene
Panomifene (International Nonproprietary Name, INN; developmental codes GYKI 13504 and EGIS 5650) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group related to tamoxifen that was under development as an antineoplastic agent by Egis Pharmaceuticals and IVAX Drug Research Institute in the 1990s for the treatment of breast cancer, but it was never marketed. It reached Phases of clinical research#Phase II, phase II clinical trials before development was terminated. The drug was described in 1981. References Abandoned drugs Primary alcohols Amines Hormonal antineoplastic drugs Trifluoromethyl compounds Selective estrogen receptor modulators Triphenylethylenes {{antineoplastic-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Afimoxifene
Afimoxifene, also known as 4-hydroxytamoxifen (4-OHT) and by its tentative brand name TamoGel, is a selective estrogen receptor modulator (SERM) of the triphenylethylene group and an active metabolite of tamoxifen. The drug is under development under the tentative brand name TamoGel as a topical gel for the treatment of hyperplasia of the breast. It has completed a phase II clinical trial for cyclical mastalgia, but further studies are required before afimoxifene can be approved for this indication and marketed. Afimoxifene is a SERM and hence acts as a tissue-selective agonist–antagonist of the estrogen receptors ERα and ERβ with mixed estrogenic and antiestrogenic activity depending on the tissue. It is also an agonist of the G protein-coupled estrogen receptor (GPER) with relatively low affinity (100–1,000 nM, relative to 3–6 nM for estradiol). In addition to its estrogenic and antiestrogenic activity, afimoxifene has been found to act as an antagonist of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ospemifene
Ospemifene (brand names Osphena and Senshio produced by Shionogi) is an oral medication indicated for the treatment of dyspareuniapain during sexual intercourseencountered by some women, more often in those who are post-menopausal. Ospemifene is a selective estrogen receptor modulator (SERM) acting similarly to an estrogen on the vaginal epithelium, building vaginal wall thickness which in turn reduces the pain associated with dyspareunia. Dyspareunia is most commonly caused by "vulvar and vaginal atrophy." The medication was approved by the FDA in February 2013 and by the European Commission for marketing in the EU in January 2015. Medical uses Ospemifene is used to treat dyspareunia. In the US it is indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy (VVA), due to menopause. In the EU it is indicated for the treatment of moderate to severe symptomatic VVA in post-menopausal women who are not candidates for local vaginal oest ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nafoxidine
Nafoxidine (; developmental code names U-11,000A) or nafoxidine hydrochloride () is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development. Nafoxidine is a long-acting estrogen receptor ligand In coordination chemistry, a lig ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Miproxifene Phosphate
Miproxifene phosphate (former developmental code name TAT-59) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was under development in Japan for the treatment of breast cancer but was abandoned and never marketed. It reached phase III clinical trials for this indication before development was discontinued. The drug is a phosphate ester and prodrug of miproxifene (DP-TAT-59) with improved water solubility that was better suited for clinical development. Miproxifene has been found to be 3- to 10-fold as potent as tamoxifen in inhibiting breast cancer cell growth in ''in vitro'' models. It is a derivative of afimoxifene (4-hydroxytamoxifen) in which an additional 4-isopropyl group is present in the β-phenyl ring In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a ben ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Miproxifene
Miproxifene (INN) (former developmental code name DP-TAT-59) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was never marketed. It is a derivative of afimoxifene (4-hydroxytamoxifen) in which an additional 4-isopropyl group is present in the β-phenyl ring. The drug has been found to be 3- to 10-fold more potent than tamoxifen in inhibiting breast cancer cell growth in ''in vitro'' models. Miproxifene is the active metabolite of miproxifene phosphate (TAT-59), a phosphate ester and prodrug of miproxifene that was developed to improve its water solubility. Miproxifene phosphate was under development for the treatment of breast cancer and reached phase III clinical trial Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, dietar ...s for this i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Idoxifene
Idoxifene (INN, USAN, BAN) (former developmental code names CB-7432, SB-223030), also known as pyrrolidino-4-iodotamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group which was under development for the treatment of breast cancer and postmenopausal osteoporosis but was never marketed.https://adisinsight.springer.com/drugs/800003448 It reached phase III clinical trials for postmenopausal osteoporosis and phase II clinical trials for breast cancer before development was discontinued in 1999 due to insufficient effectiveness in both cases. Chemistry Synthesis A large-scale chemical synthesis As a topic of chemistry, chemical synthesis (or combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In mod ... of idoxifene has been devised. References External links Idoxifene - AdisInsight ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fispemifene
Fispemifene (INN, USAN) (developmental code name HM-101) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed for the treatment of male hypogonadism but was abandoned and never marketed. It reached phase II clinical trials for this indication before development was terminated in March 2016. The drug failed to achieve statistical significance on key effectiveness endpoint An endpoint, end-point or end point may refer to: * Endpoint (band), a hardcore punk band from Louisville, Kentucky * Endpoint (chemistry), the conclusion of a chemical reaction, particularly for titration * Outcome measure, a measure used as an e ...s in clinical trials and was discontinued by its developer for strategic reasons. See also * Ospemifene References External links Fispemifene - AdisInsight Primary alcohols Organochlorides Progonadotropins Selective estrogen receptor modulators Triphenylethylenes {{genito-urinary-drug-s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Etacstil
Etacstil (developmental code names GW-5638, DPC974) is an orally active, nonsteroidal, combined selective estrogen receptor modulator (SERM) and selective estrogen receptor degrader (SERD) that was developed for the treatment of estrogen receptor-positive breast cancer. It was shown to overcome antiestrogen (tamoxifen, aromatase inhibitor, fulvestrant) resistance in breast cancer by altering the shape of the estrogen receptor, thus exhibiting SERD properties. Etacstil is a tamoxifen derivative and one of the first drugs to overcome tamoxifen-resistance. It is the predecessor of GW-7604, of which etacstil is a prodrug (GW-7604 being the 4-hydroxy metabolite of etacstil). This is analogous to the case of tamoxifen being a prodrug of afimoxifene (4-hydroxytamoxifen). Etacstil was developed in the early 1990s by Duke University, Glaxo Wellcome, and later, Dupont. In 2001, Bristol Myers-Squibb (BMS) acquired Dupont, and for non-scientific, corporate reasons, closed the trial and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Endoxifen
Endoxifen, also known as 4-hydroxy-''N''-desmethyltamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group as well as a protein kinase C (PKC) inhibitor. It is under development for the treatment of estrogen receptor-positive breast cancer and for the treatment of mania in bipolar disorder. It is taken by mouth. Endoxifen is an active metabolite of tamoxifen and has been found to be effective in patients that have failed previous hormonal therapies (tamoxifen, aromatase inhibitors, and fulvestrant). The prodrug tamoxifen is metabolized by the CYP2D6 enzyme to produce endoxifen and afimoxifene (4-hydroxytamoxifen). Currently, endoxifen is approved by Drugs Controller General of India for the acute treatment of manic episode with or without mixed features of Bipolar I disorder. It is manufactured and sold by Intas Pharmaceuticals under the brand name Zonalta. Medical uses Bipolar disorder Endoxifen is used to treat manic or mi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Droloxifene
Droloxifene (INN, USAN) (former developmental code names FK-435, ICI-79280, K-060, K-21060E, RP-60850), also known as 3-hydroxytamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed originally in Germany and later in Japan for the treatment of breast cancer, osteoporosis in men and postmenopausal women, and cardiovascular disorders but was abandoned and never marketed. It reached phase II and phase III clinical trials for these indications before development was discontinued in 2000. The drug was found to be significantly less effective than tamoxifen in the treatment of breast cancer in two phase III clinical trials. Droloxifene is an analogue of tamoxifen, specifically 3-hydroxytamoxifen, but has been said to have 10- to 60-fold increased affinity for the estrogen receptor and reduced partial estrogen agonistic activity. The affinity of droloxifene for the estrogen receptor ranges from 0.2 to 15.2% rela ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
