Prolame

{{short description|Chemical compound}}

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| IUPAC_name = (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

| image = Prolame.svg

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| UNII = O0UN4KN1EV

| CAS_number = 99876-41-2

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| PubChem = 127441

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| ChemSpiderID = 113081

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| C=21 | H=31 | N=1 | O=2

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCO)CCC4=C3C=CC(=C4)O

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = FRZIQVNLLGECCX-MJCUULBUSA-N

| synonyms = 17β-((3-Hydroxypropyl)amino)estradiol; 17β-[(3-Hydroxypropyl)amino]estra-1,3,5(10)-trien-3-ol

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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.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1025|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1025–}}{{cite journal | vauthors = Fernández JM, Rubio-Arroyo MF, Soriano-García M, Toscano RA, Pérez-César MC | title = 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 | journal = Steroids | volume = 45 | issue = 2 | pages = 151–7 | year = 1985 | pmid = 3841424 | doi = 10.1016/0039-128x(85)90044-3| s2cid = 45993880 }}{{cite journal | vauthors = 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 | title = The anticoagulant effect of prolame, N-(3-hydroxy-1,3,5(10)estratrien-17 beta-yl)-3-hydroxypropylamine, a novel amino-estrogen | journal = Steroids | volume = 45 | issue = 2 | pages = 159–70 | year = 1985 | pmid = 3841425 | doi = 10.1016/0039-128x(85)90045-5| s2cid = 24724648 }}{{cite journal | vauthors = Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, García R, Silva G, Larrea F | title = In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta-aminoestrogens | journal = J. Steroid Biochem. Mol. Biol. | volume = 73 | issue = 1–2 | pages = 59–66 | year = 2000 | pmid = 10822025 | doi = 10.1016/s0960-0760(00)00053-4| s2cid = 40211307 }}{{cite book|author=Alan D. Michelson|title=Platelets|url=https://books.google.com/books?id=yF5WQdAcdfcC&pg=PA314|date=31 December 2012|publisher=Academic Press|isbn=978-0-12-387838-0|pages=314–}}