Butolame

{{Short description|Chemical compound}}

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| IUPAC_name = (8R,9S,13S,14S,17S)-17-(4-Hydroxybutylamino)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol

| image = Butolame.svg

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| CAS_number = 150748-23-5

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| UNII = 4UPR2B5SG4

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| PubChem = 197608

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| ChemSpiderID = 171062

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| C=22 | H=33 | N=1 | O=2

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

| StdInChI_Ref =

| StdInChI = 1S/C22H33NO2/c1-22-11-10-18-17-7-5-16(25)14-15(17)4-6-19(18)20(22)8-9-21(22)23-12-2-3-13-24/h5,7,14,18-21,23-25H,2-4,6,8-13H2,1H3/t18-,19-,20+,21+,22+/m1/s1

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| StdInChIKey = AXFQQAQJYIXKGS-AANPDWTMSA-N

| synonyms = 17β-((4-Hydroxybutyl)amino)estradiol; 17β-[(4-Hydroxybutyl)amino]estra-1,3,5(10)-trien-3-ol

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Butolame, also known as 17β-((4-hydroxybutyl)amino)estradiol, is a synthetic, steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was first described in 1993 and was never marketed.{{cite book | vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zmpqAAAAMAAJ|year=2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2352}}{{cite journal | vauthors = Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, Castro D, Cruz-Almanza R, Mandoki JJ | display-authors = 6 | title = Anticoagulant and estrogenic effects of two new 17 beta-aminoestrogens, butolame [17 beta-(4-hydroxy-1-butylamino)-1,3,5(10)-estratrien-3-ol] and pentolame [17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol] | journal = Steroids | volume = 58 | issue = 10 | pages = 457–461 | date = October 1993 | pmid = 8256254 | doi = 10.1016/0039-128x(93)90002-5 | s2cid = 54381037 }}{{cite journal | vauthors = Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, García R, Silva G, Larrea F | display-authors = 6 | title = In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta-aminoestrogens | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 73 | issue = 1–2 | pages = 59–66 | date = May 2000 | pmid = 10822025 | doi = 10.1016/s0960-0760(00)00053-4 | s2cid = 40211307 }}