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Chemical compound
Pharmaceutical compound
Prolame Other names 17β-((3-Hydroxypropyl)amino)estradiol; 17β-[(3-Hydroxypropyl)amino]estra-1,3,5(10)-trien-3-ol
(8R ,9S ,13S ,14S ,17S )-17-(3-Hydroxypropylamino)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a ]phenanthren-3-ol
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 21 H 31 N O 2 Molar mass −1 3D model (JSmol )
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCO)CCC4=C3C=CC(=C4)O
InChI=1S/C21H31NO2/c1-21-10-9-17-16-6-4-15(24)13-14(16)3-5-18(17)19(21)7-8-20(21)22-11-2-12-23/h4,6,13,17-20,22-24H,2-3,5,7-12H2,1H3/t17-,18-,19+,20+,21+/m1/s1
Key:FRZIQVNLLGECCX-MJCUULBUSA-N
Prolame , also known as 17β-((3-hydroxypropyl)amino)estradiol , is a synthetic , steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was first described in 1985 but was never marketed.[ 1] [ 2] [ 3] [ 4] [ 5]
^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^ Fernández JM, Rubio-Arroyo MF, Soriano-García M, Toscano RA, Pérez-César MC (1985). "Synthesis and molecular structure of prolame, N-(3-hydroxy-1,3,5(10)-estratrien-17 beta-yl)-3-hydroxypropylamine; an amino-estrogen with prolonged anticoagulant and brief estrogenic effects". Steroids . 45 (2): 151–7. doi :10.1016/0039-128x(85)90044-3 . PMID 3841424 . S2CID 45993880 . ^ Rubio-Póo C, Mandoki JJ, Mendoza-Patiño N, Lemini C, de la Peña A, Cruz F, Zavala E, Silva G, Garcia-Mondragón J, Fernández JM (1985). "The anticoagulant effect of prolame, N-(3-hydroxy-1,3,5(10)estratrien-17 beta-yl)-3-hydroxypropylamine, a novel amino-estrogen". Steroids . 45 (2): 159–70. doi :10.1016/0039-128x(85)90045-5 . PMID 3841425 . S2CID 24724648 . ^ Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, García R, Silva G, Larrea F (2000). "In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta-aminoestrogens". J. Steroid Biochem. Mol. Biol . 73 (1–2): 59–66. doi :10.1016/s0960-0760(00)00053-4 . PMID 10822025 . S2CID 40211307 . ^ Alan D. Michelson (31 December 2012). Platelets ISBN 978-0-12-387838-0
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
