Orestrate
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 408.582 g·mol−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] It is the C3 propionate ester and C17β-(1-cyclohexenyl ) ether of estradiol .[ 1] [ 5]
See also
References
^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 898, 905. 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 . The Academy. p. 7. 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 -Estradiol
Epiestriol (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 )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown