Butolame

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.[1][2][3]

Butolame
Clinical data
Other names17β-((4-Hydroxybutyl)amino)estradiol; 17β-[(4-Hydroxybutyl)amino]estra-1,3,5(10)-trien-3-ol
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H33NO2
Molar mass343.511 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCCO)CCC4=C3C=CC(=C4)O
InChI
  • InChI=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
  • Key:AXFQQAQJYIXKGS-AANPDWTMSA-N

References
  1. Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2352. ISBN 978-3-527-30247-5.
  2. Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, Castro D, Cruz-Almanza R, Mandoki JJ (1993). "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]". Steroids. 58 (10): 457–61. doi:10.1016/0039-128x(93)90002-5. PMID 8256254. S2CID 54381037.
  3. 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.


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