Chemical compound
Pharmaceutical compound
Methylestradiol Clinical data Trade names Ginecosid, Ginecoside, Mediol, Renodiol Other names NSC-52245; 17α-Methylestradiol; 17α-ME; 17α-Methylestra-1,3,5(10)-triene-3,17β-diol Routes of By mouth [ 1] Drug class Estrogen Identifiers (8R ,9S ,13S ,14S ,17S )-13,17-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H -cyclopenta[a ]phenanthrene-3,17-diol
CAS Number PubChem CID ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.005.572 Chemical and physical data Formula C 19 H 26 O 2 Molar mass −1 3D model (JSmol ) InChI=1S/C19H26O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h4,6,11,15-17,20-21H,3,5,7-10H2,1-2H3/t15-,16-,17+,18+,19+/m1/s1
Key:JXQJDYXWHSVOEF-GFEQUFNTSA-N
Methylestradiol , sold under the brand namesGinecosid ,Ginecoside ,Mediol , andRenodiol , is anestrogen medication which is used in the treatment ofmenopausal symptoms .[ 2] [ 3] [ 4] normethandrone , aprogestin andandrogen /anabolic steroid medication.[ 3] [ 4] by mouth .[ 1]
Side effects of methylestradiol includenausea ,breast tension ,edema , andbreakthrough bleeding among others.[ 5] estrogen , or anagonist of theestrogen receptors , thebiological target of estrogens likeestradiol .[ 6]
Methylestradiol is or has been marketed inBrazil ,Venezuela , andIndonesia .[ 3] radiopharmaceutical for theestrogen receptor .[ 7]
Methylestradiol is used in combination with the progestin and androgen/anabolic steroidnormethandrone (methylestrenolone) in the treatment ofmenopausal symptoms .[ 3] [ 4]
Methylestradiol is marketed in combination withnormethandrone in the form oforal tablets containing 0.3 mg methylestradiol and 5 mg normethandrone.[ 8] [ 9]
Side effects of methylestradiol includenausea ,breast tension ,edema , andbreakthrough bleeding .[ 5]
Methylestradiol is anestrogen , or anagonist of theestrogen receptor .[ 6] affinity for the estrogen receptor thanestradiol orethinylestradiol .[ 6]
Methylestradiol is anactive metabolite of the androgens/anabolic steroidsmethyltestosterone (17α-methyltestosterone),metandienone (17α-methyl-δ1 -testosterone), andnormethandrone (17α-methyl-19-nortestosterone), and is responsible for theirestrogenic side effects , such asgynecomastia andfluid retention .[ 10] [ 11] [ 12]
Relative affinities (%) of methylestradiol and related steroids Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1 Ethinylestradiol 15–25 1–3 112 1–3 <1 ? ? Methylestradiol 3–10, 15–25 1–3 67 1–3 <1 ? ? Methyltestosterone 3 45, 100–125 ? 1–5 ? 5 ? Normethandrone 100 146 <0.1 1.5 0.6 ? ? Sources: Values are percentages (%). Referenceligands (100%) wereprogesterone for thePR Tooltip progesterone receptor ,testosterone for theAR Tooltip androgen receptor ,E2 for theER Tooltip estrogen receptor ,DEXA Tooltip dexamethasone for theGR Tooltip glucocorticoid receptor ,aldosterone for theMR Tooltip mineralocorticoid receptor ,DHT Tooltip dihydrotestosterone forSHBG Tooltip sex hormone-binding globulin , andcortisol forCBG Tooltip Corticosteroid-binding globulin .Sources: [ 13] [ 6] [ 14] [ 15]
Due to the presence of its C17αmethyl group , methylestradiol cannot be deactivated byoxidation of the C17βhydroxyl group , resulting in improvedmetabolic stability andpotency relative toestradiol .[ 10] ethinylestradiol and its C17αethynyl group .[ 10]
Methylestradiol, or 17α-methylestradiol (17α-ME), also known as 17α-methylestra-1,3,5(10)-triene-3,17β-diol, is asynthetic estrane steroid and aderivative ofestradiol .[ 2] [ 3] methyl group at the C17α positions.[ 2] [ 3] ethinylestradiol (17α-ethynylestradiol) andethylestradiol (17α-ethylestradiol).[ 2] cyclopentyl ether of methylestradiol has been studied and shows greateroral potency than methylestradiol in animals, similarly toquinestrol (ethinylestradiol 3-cyclopentyl ether) andquinestradol (estriol 3-cyclopentyl ether).[ 16]
The procedure involving organometallic addition ofmethyl lithium toestrone works in very high yield but not theGrignard reagent .[ 17] [ 18]
Methylestradiol was first marketed, alone as Follikosid and in combination withmethyltestosterone as Klimanosid, in 1955.[ 19] [ 20] [ 21] [ 22]
Society and culture [ edit ] Methylestradiol has not been assigned anINN Tooltip International Nonproprietary Name or other formal name designations.[ 2] [ 3] generic name inEnglish andGerman ismethylestradiol , inFrench isméthylestradiol , and inSpanish ismetilestadiol .[ 3] 17α-methylestradiol .[ 3]
Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination withnormethandrone .[ 3] [ 2]
Methylestradiol is or has been marketed inBrazil ,Venezuela , andIndonesia .[ 3]
^a b Hegemann O (May 1959). "[Oral hormonal treatment with methylestrene-olone & methylestradiol as early pregnancy tests]".Die Medizinische (in German).4 (21):1032– 1033.PMID 13673847 . ^a b c d e f Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c d e f g h i j k "Methylestradiol" .Drugs.com . Retrieved2 January 2016 .^a b c IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007).Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy ISBN 978-92-832-1291-1 ^a b Wittlinger H (1980). "Clinical Effects of Estrogens".Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones . pp. 67– 71.doi :10.1007/978-3-642-67568-3_10 .ISBN 978-3-642-67570-6 ^a b c d Ojasoo T, Raynaud JP (November 1978)."Unique steroid congeners for receptor studies" .Cancer Research .38 (11 Pt 2):4186– 4198.PMID 359134 . ^ Feenstra A, Vaalburg W, Nolten GM, Reiffers S, Talma AG, Wiegman T, et al. (June 1983). "Estrogen receptor binding radiopharmaceuticals: II. Tissue distribution of 17 alpha-methylestradiol in normal and tumor-bearing rats".Journal of Nuclear Medicine .24 (6):522– 528.PMID 6406650 . ^ Unlisted Drugs Batynid. C. Each dragee contains: normethandrone, 5 mg.; and methylestradiol, 0.3 mg. E. (Formerly) Gynaekosid. M. Boehringer Biochemia, Florence. A. Estrogenic; Rx of secondary amenorrhea. R. Notiz Med Farm 32;295, Nov-Dec 81. ^ Akingba JB, Ayodeji EA (February 1966). "Amenorrhea as a leading symptom of choriocarcinoma".The Journal of Obstetrics and Gynaecology of the British Commonwealth .73 (1):153– 155.doi :10.1111/j.1471-0528.1966.tb05137.x .PMID 5948541 .S2CID 38008851 . ^a b c Thieme D, Hemmersbach P (18 December 2009).Doping in Sports ISBN 978-3-540-79088-4 ^ Llewellyn W (2011).Anabolics ISBN 978-0-9828280-1-4 ^ Friedl KE (1990). "Reappraisal of the health risks associated with the use of high doses of oral and injectable androgenic steroids".NIDA Research Monograph .102 :142– 177.PMID 1964199 . ^ Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979)."Receptor Binding as a Tool in the Development of New Bioactive Steroids" .Drug Design . pp. 169– 214.doi :10.1016/B978-0-12-060308-4.50010-X .ISBN 9780120603084 ^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors".Journal of Steroid Biochemistry .27 (1– 3):255– 269.doi :10.1016/0022-4731(87)90317-7 .PMID 3695484 . ^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, et al. (January 1980). "Steroid hormone receptors and pharmacology".Journal of Steroid Biochemistry .12 :143– 157.doi :10.1016/0022-4731(80)90264-2 .PMID 7421203 . ^ Falconi G, Rossi GL, Ercoli A (September 1970). James VH (ed.).Quinestrol and other cyclopentyl ethers of estrogenic steroids: different rates of storage in body fat 218– 219. Archived fromthe original on 28 March 2018. ^ Stoeck Georg & Voigt Hans,U.S. patent 2,857,405 ^ Boivin, R. P., Luu-The, V., Lachance, R., Labrie, F., Poirier, D. (1 November 2000)."Structure−Activity Relationships of 17α-Derivatives of Estradiol as Inhibitors of Steroid Sulfatase" .Journal of Medicinal Chemistry .43 (23):4465– 4478.doi :10.1021/jm0001166 . ^ "Neue Spezialitäten".Klinische Wochenschrift .33 (31– 32):773– 774. 1955.doi :10.1007/BF01473523 .ISSN 0023-2173 .S2CID 1678069 . ^ Kahr H (8 March 2013).Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur ISBN 978-3-7091-5694-0 ^ Arends G, Zörnig H, Hager H, Frerichs G, Kern W (14 December 2013).Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte 1156– 1157, 1164.ISBN 978-3-662-36329-4 ^ Helwig B (1956).Moderne Arzneimittel: eine Spezialitätenkunde nach Indikationsgebieten für Ärzte und Apotheker
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
