Pentolame

Pentolame, also known as 17β-((5-hydroxypentyl)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]

Pentolame
Clinical data
Other names17β-((5-Hydroxypentyl)amino)estradiol; 17β-[(5-Hydroxypentyl)amino]estra-1,3,5(10)-trien-3-ol
Identifiers
IUPAC name
  • (8R,9S,13S,14S,17S)-17-(5-Hydroxypentylamino)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC23H35NO2
Molar mass357.538 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCCCO)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C23H35NO2/c1-23-12-11-19-18-8-6-17(26)15-16(18)5-7-20(19)21(23)9-10-22(23)24-13-3-2-4-14-25/h6,8,15,19-22,24-26H,2-5,7,9-14H2,1H3/t19-,20-,21+,22+,23+/m1/s1
  • Key:CYIRNKIFROUCMA-VROINQGHSA-N

References
  1. 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.
  2. Lemus AE, Jaimez R, Lemini C, Menjivar M, Silva G, Rubio-Poo C, Valenzuela F, Larrea F (1998). "Estrogenic effects of the synthetic aminoestrogen 17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol (pentolame)". Steroids. 63 (7–8): 433–8. doi:10.1016/s0039-128x(98)00046-4. PMID 9654651. S2CID 13582499.
  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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