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Chemical compound
Orestrate Other names Estradiol 3-propionate 17β-(1-cyclohexenyl) ether; 17β-(Cyclohexen-1-yloxy)-estra-1,3,5(10)-trien-3-ol propionate Drug class Estrogen ; Estrogen ester
[(8R ,9S ,13S ,14S ,17S )-17-(Cyclohexen-1-yloxy)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a ]phenanthren-3-yl] propanoate
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 27 H 36 O 3 Molar mass −1 3D model (JSmol )
CCC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4OC5=CCCCC5)C
InChI=1S/C27H36O3/c1-3-26(28)30-20-10-12-21-18(17-20)9-11-23-22(21)15-16-27(2)24(23)13-14-25(27)29-19-7-5-4-6-8-19/h7,10,12,17,22-25H,3-6,8-9,11,13-16H2,1-2H3/t22-,23-,24+,25+,27+/m1/s1
Key:VYAXJSIVAVEVHF-RYIFMDQWSA-N
Orestrate (INN Tooltip International Nonproprietary Name ), also known as estradiol 3-propionate 17β-(1-cyclohexenyl) ether , is an estrogen medication and estrogen ester which was never marketed.[ 1] [ 2] [ 3] [ 4] [ 5] propionate ester and C17β-(1-cyclohexenyl ) ether of estradiol .[ 1] [ 5]
^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^ Gardi R, Vitali R, Falconi G, Ercoli A (February 1973). "1,3,5(10)-Estratrien-17 -yl enol ethers and acetals. New classes of orally and parenterally active estrogenic derivatives". Journal of Medicinal Chemistry . 16 (2): 123–127. doi :10.1021/jm00260a009 . PMID 4683106 . ^ Galletti F, Gardi R (April 1974). "Effect of two orally active estradiol derivatives on sulfobromphthalein retention in rats". Pharmacological Research Communications . 6 (2): 135–145. doi :10.1016/s0031-6989(74)80021-4 . PMID 4438394 . ^ List PH, Hörhammer L (12 March 2013). "Orestratum" . Chemikalien und Drogen Teil A: N-Q . Springer-Verlag. pp. 331–. ISBN 978-3-642-65035-2 ^ a b Roche EB, Academy of Pharmaceutical Sciences, ((Medicinal Chemistry Section (1977). Design of biopharmaceutical properties through prodrugs and analogs: a symposium ISBN 978-0-917330-16-2
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 and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , 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
