Butolame

Butolame
Clinical data
Other names	17β-((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	150748-23-5 ;
PubChem CID	197608;
ChemSpider	171062;
UNII	4UPR2B5SG4;
CompTox Dashboard (EPA)	DTXSID80934056 ;
Chemical and physical data
Formula	C22H33NO2
Molar mass	343.511 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2352. ISBN 978-3-527-30247-5.
^ Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, et al. (October 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): 457–461. doi:10.1016/0039-128x(93)90002-5. PMID 8256254. S2CID 54381037.
^ Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, et al. (May 2000). "In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta-aminoestrogens". The Journal of Steroid Biochemistry and Molecular Biology. 73 (1–2): 59–66. doi:10.1016/s0960-0760(00)00053-4. PMID 10822025. S2CID 40211307.