Hexolame

Hexolame, also known as 17β-((6-hydroxyhexyl)amino)estradiol, is a synthetic, steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was first described in 1990 and was never marketed.[1][2][3]

Hexolame
Clinical data
Other names17β-((6-Hydroxyhexyl)amino)estradiol; 17β-[(6-Hydroxyhexyl)amino]estra-1,3,5(10)-trien-3-ol; N-(3-Hydroxy-1,3,5(10)-estratrien 17-yl)-6-hydroxyhexylamine
Identifiers
IUPAC name
  • (8R,9S,13S,14S,17S)-17-(6-Hydroxyhexylamino)-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
FormulaC24H37NO2
Molar mass371.565 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCCCCO)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C24H37NO2/c1-24-13-12-20-19-9-7-18(27)16-17(19)6-8-21(20)22(24)10-11-23(24)25-14-4-2-3-5-15-26/h7,9,16,20-23,25-27H,2-6,8,10-15H2,1H3/t20-,21-,22+,23+,24+/m1/s1
  • Key:DPRSBWGNESQTLG-DJCPXJLLSA-N

References
  1. Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 12610. ISBN 978-3-527-30247-5.
  2. Rubio-Póo C, Lemini C, García-Mondragón J, de la Peña A, Jayme V, Mendoza-Patiño N, Zavala E, Silva G, Blickenstaff RT, Fernández JM (1990). "The anticoagulant effect of hexolame, N-(3-hydroxy-1,3,5(10)-estratrien-17 beta-yl)-6-hydroxyhexylamine, another amino-estrogen with prolonged anticoagulant effect". Steroids. 55 (2): 83–6. doi:10.1016/0039-128x(90)90030-f. PMID 2326832. S2CID 32937513.
  3. Rubio-Póo C, Lemini C, Silva G, García-Mondragón J, Zavala E, Castro D, Mendoza-Patiño N, Mandoki JJ (1993). "Comparison of the time course of anticoagulant and estrogenic effects of prolame, butolame, pentolame and hexolame, a homologous series of 17 beta-amino estrogens". Proc. West. Pharmacol. Soc. 36: 143–7. PMID 8378368.


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