Pharmaceutical drug
Pharmaceutical compound
Triphenylchloroethylene (TPCE ; brand namesGynosone ,Oestrogyl ), ortriphenylchlorethylene , also known aschlorotriphenylethylene or asphenylstilbene chloride , is asynthetic nonsteroidal estrogen of thetriphenylethylene group that was marketed in the 1940s for the treatment ofmenopausal symptoms ,vaginal atrophy ,lactation suppression , and all otherestrogen -indicated conditions.[ 1] [ 2] [ 3]
Theestrogenic effects of triphenylethylene, the parent compound of triphenylchloroethylene, were discovered in 1937.[ 4] halogen substituent .[ 2] [ 5] duration of action when administered viasubcutaneous injection but a duration similar to that ofdiethylstilbestrol orestradiol benzoate when administeredorally .[ 2] [ 6] [ 7] triphenylmethylethylene , triphenylchloroethylene was studied in 1944 bySir Alexander Haddow for the treatment ofbreast cancer and was found to be significantly effective, and this is historically notable in that it was the first time that high-dose estrogens were found to be effective in the treatment of breast cancer.[ 8] [ 9]
Chlorotrianisene , or tri-p -anisylchloroethylene (TACE), is a potent marketed estrogen and aderivative of triphenylchloroethylene in which each of the threephenyl rings has been substituted with a 4-methoxy group .[ 5] [ 10] Estrobin , or DBE, is a related, never-marketed estrogen in which there is abromine in place of thechlorine and two of the three phenyl rings haveethoxy groups .[ 5] Broparestrol , or BDPE is a marketedselective estrogen receptor modulator (SERM) that has a bromine in place of the chlorine of triphenylchloroethylene and a 4-ethyl group on one of the phenyl rings. The SERMclomifene is also a derivative of triphenylchloroethylene.[ 11]
^ Negwer M, Scharnow HG (2001).Organic-chemical drugs and their synonyms: (an international survey) 1861– 1862.ISBN 978-3-527-30247-5 C20H15Cl 18084-97-4 Chlorotriphenylethene = Triphenylchloroethylene = Phenylstilbene chloride = 1,1',1"-(1-Chloro-1-ethenyl-2-ylidene)tris[benzene] (•) S Gynosone, Oestrogyl, Phenylstilbene chloride U Synthetic estrogen ^a b c Emmens CW (July 1947). "Halogen-substituted oestrogens related to triphenylethylene".The Journal of Endocrinology .5 (3):170– 173.doi :10.1677/joe.0.0050170 .PMID 20259249 . ^ " . Advertisement.Proc R Soc Med .39 (11). Sep 1946.PMC 2181944 ^ Li JJ (3 April 2009)."Genesis of Statins" .Triumph of the Heart: The Story of Statins . Oxford University Press, USA. pp. 33–.ISBN 978-0-19-532357-3 ^a b c Solmssen UV (December 1945). "Synthetic estrogens and the relation between their structure and their activity".Chemical Reviews .37 (3):481– 598.doi :10.1021/cr60118a004 .PMID 21013428 . ^ Jordon VC, Koch R, Lieberman ME (1986)."Structure-Activity Relationships of Nonsteroidal Estrogens and Antiestrogens" . In Jordan VC (ed.).Estrogen/antiestrogen Action and Breast Cancer Therapy . University of Wisconsin Press. pp. 23–.ISBN 978-0-299-10480-1 ^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013)."Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens" .Tamoxifen: Pioneering Medicine in Breast Cancer . Springer Science & Business Media. pp. 4–.ISBN 978-3-0348-0664-0 ^ Lewis-Wambi J, Jordan VC (27 May 2013)."Diethylstilbestrol: A Tragedy in Reproductive Endocrinology But a Pioneering Cancer Treatment" . In Jordan VC (ed.).Estrogen Action, Selective Estrogen Receptor Modulators and Women's Health: Progress and Promise . World Scientific. pp. 42–.ISBN 978-1-84816-959-3 ^ Wagener DJ (13 July 2009)."The history of the hormonal treatment of cancer" .The History of Oncology . Bohn Stafleu van Loghum. pp. 189–.ISBN 978-90-313-6143-4 ^ Lisi F (2006)."Adjunctions to Clomiphene Citrate" . In Allahbadia G (ed.).Contemporary Perspectives on Assisted Reproductive Technology . Elsevier India. pp. 18–.ISBN 978-81-8147-782-8 ^ Shoham Z, Howles CM (27 June 2012)."Drugs used for ovarian stimulation: Clomiphene citrate, aromatase inhibitors, metformin, gonadotropins, gonadotropin-releasing hormone analogs and recombinant gonadotropins" . In Gardner DK, Weissman A, Howles CM, Shoham Z (eds.).Textbook of Assisted Reproductive Techniques Fourth Edition: Volume 2: Clinical Perspectives . CRC Press. pp. 51–.ISBN 978-1-84184-972-0
Estrogens
ER Tooltip Estrogen receptor agonistsSteroidal: Alfatradiol Certainandrogens /anabolic steroids (e.g.,testosterone ,testosterone esters ,methyltestosterone ,metandienone ,nandrolone esters ) (via estrogenic metabolites) Certainprogestins (e.g.,norethisterone ,noretynodrel ,etynodiol diacetate ,tibolone ) Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g.,estradiol acetate ,estradiol benzoate ,estradiol cypionate ,estradiol enanthate ,estradiol undecylate ,estradiol valerate ,polyestradiol phosphate ,estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g.,estriol succinate ,polyestriol phosphate )Estrogenic substances Estrone Estrone esters Ethinylestradiol # Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA) Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins Androgens /anabolic steroids (e.g.,testosterone ,testosterone esters ,nandrolone esters ,oxandrolone ,fluoxymesterone )D2 receptor antagonists (prolactin releasers) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )GnRH agonists (e.g.,leuprorelin ,goserelin )GnRH antagonists (e.g.,cetrorelix ,elagolix )Progestogens (e.g.,chlormadinone acetate ,cyproterone acetate ,gestonorone caproate ,hydroxyprogesterone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
ER Tooltip Estrogen receptor
Agonists Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estrofurate Estrogenic substances Estromustine Estrone Etamestrol (eptamestrol) Ethinylandrostenediol Ethinylestradiol Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g.,anethole ,anol ,dianethole ,dianol ,photoanethole )Chalconoids (e.g.,isoliquiritigenin ,phloretin ,phlorizin (phloridzin) ,wedelolactone )Coumestans (e.g.,coumestrol ,psoralidin )Flavonoids (incl.7,8-DHF ,8-prenylnaringenin ,apigenin ,baicalein ,baicalin ,biochanin A ,calycosin ,catechin ,daidzein ,daidzin ,ECG ,EGCG ,epicatechin ,equol ,formononetin ,glabrene ,glabridin ,genistein ,genistin ,glycitein ,kaempferol ,liquiritigenin ,mirificin ,myricetin ,naringenin ,penduletin ,pinocembrin ,prunetin ,puerarin ,quercetin ,tectoridin ,tectorigenin )Lavender oil Lignans (e.g.,enterodiol ,enterolactone ,nyasol (cis -hinokiresinol) )Metalloestrogens (e.g.,cadmium )Pesticides (e.g.,alternariol ,dieldrin ,endosulfan ,fenarimol ,HPTE ,methiocarb ,methoxychlor ,triclocarban ,triclosan )Phytosteroids (e.g.,digitoxin (digitalis ),diosgenin ,guggulsterone )Phytosterols (e.g.,β-sitosterol ,campesterol ,stigmasterol )Resorcylic acid lactones (e.g.,zearalanone ,α-zearalenol ,β-zearalenol ,zearalenone ,zeranol (α-zearalanol) ,taleranol (teranol, β-zearalanol) )Steroid -like (e.g.,deoxymiroestrol ,miroestrol )Stilbenoids (e.g.,resveratrol ,rhaponticin )Synthetic xenoestrogens (e.g.,alkylphenols ,bisphenols (e.g.,BPA ,BPF ,BPS ),DDT ,parabens ,PBBs ,PHBA ,phthalates ,PCBs )Others (e.g.,agnuside ,rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
