Prolame

Prolame, also known as 17β-((3-hydroxypropyl)amino)estradiol, is a synthetic, steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was first described in 1985 but was never marketed.[1][2][3][4][5]

Prolame
Clinical data
Other names17β-((3-Hydroxypropyl)amino)estradiol; 17β-[(3-Hydroxypropyl)amino]estra-1,3,5(10)-trien-3-ol
Identifiers
IUPAC name
  • (8R,9S,13S,14S,17S)-17-(3-Hydroxypropylamino)-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
FormulaC21H31NO2
Molar mass329.484 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCO)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C21H31NO2/c1-21-10-9-17-16-6-4-15(24)13-14(16)3-5-18(17)19(21)7-8-20(21)22-11-2-12-23/h4,6,13,17-20,22-24H,2-3,5,7-12H2,1H3/t17-,18-,19+,20+,21+/m1/s1
  • Key:FRZIQVNLLGECCX-MJCUULBUSA-N

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1025–. ISBN 978-1-4757-2085-3.
  2. Fernández JM, Rubio-Arroyo MF, Soriano-García M, Toscano RA, Pérez-César MC (1985). "Synthesis and molecular structure of prolame, N-(3-hydroxy-1,3,5(10)-estratrien-17 beta-yl)-3-hydroxypropylamine; an amino-estrogen with prolonged anticoagulant and brief estrogenic effects". Steroids. 45 (2): 151–7. doi:10.1016/0039-128x(85)90044-3. PMID 3841424. S2CID 45993880.
  3. Rubio-Póo C, Mandoki JJ, Mendoza-Patiño N, Lemini C, de la Peña A, Cruz F, Zavala E, Silva G, Garcia-Mondragón J, Fernández JM (1985). "The anticoagulant effect of prolame, N-(3-hydroxy-1,3,5(10)estratrien-17 beta-yl)-3-hydroxypropylamine, a novel amino-estrogen". Steroids. 45 (2): 159–70. doi:10.1016/0039-128x(85)90045-5. PMID 3841425. S2CID 24724648.
  4. 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.
  5. Alan D. Michelson (31 December 2012). Platelets. Academic Press. pp. 314–. ISBN 978-0-12-387838-0.


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