SEP-225289

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SEP-225289
SEP-225289 structure.png
Systematic (IUPAC) name
(1R)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine
Clinical data
Legal status ?
Identifiers
CAS number 229639-56-9 N
ATC code ?
PubChem CID 9900576
ChemSpider 8076231 N
Chemical data
Formula C15H22ClN 
Mol. mass 251.794 g/mol
 N (what is this?)  (verify)

SEP-225,289 is an antidepressant drug derived from the active enantiomer of sibutramine, which was being developed by Sepracor. It is a so-called triple reuptake inhibitor (TRI).[1][2][3]

Similarity to Sibutramine[edit]

As can be seen by analyzing the molecular structure, SEP-225289 is a single isomer of sibutramine that has been N-dimethylated to yield a primary amine compound. According to one source, makes the compound stronger as a catecholaminergic relative to its actions on serotonin.[4] Apparently, both isomers of sibutramine are active but it is the R enantiomer that is held accountable for its anorectic action.

References[edit]

  1. ^ Chen Z, Skolnick P (September 2007). "Triple uptake inhibitors: therapeutic potential in depression and beyond". Expert Opin Investig Drugs 16 (9): 1365–77. doi:10.1517/13543784.16.9.1365. PMID 17714023. 
  2. ^ DeLorenzo C, Lichenstein S, Schaefer K, Dunn J, Marshall R, Organisak L, Kharidia J, Robertson B, Mann JJ, Parsey RV (July 2011). "SEP-225289 serotonin and dopamine transporter occupancy: a PET study". J. Nucl. Med. 52 (7): 1150–5. doi:10.2967/jnumed.110.084525. PMID 21680689. 
  3. ^ Ziegler, L.; Küffer, G.; Euler, E.; Wilhelm, K. (1990). "Arthrographic imaging of ganglions of the hand". RoFo : Fortschritte auf dem Gebiete der Rontgenstrahlen und der Nuklearmedizin 153 (2): 143–146. doi:10.1055/s-2008-1033352. PMID 2168068.  edit
  4. ^ Glick, S. D.; Haskew, R. E.; Maisonneuve, I. M.; Carlson, J. N.; Jerussi, T. P. (2000). "Enantioselective behavioral effects of sibutramine metabolites". European Journal of Pharmacology 397 (1): 93–102. doi:10.1016/S0014-2999(00)00216-8. PMID 10844103.  edit

Further reading[edit]

Original Sibutramine patents
Liming Shao Patent
  • US application 2007203111, Shao L, Wang F, Malcolm SC, Hewitt MC, Bush LR, Ma J, Varney MA, Campbell U, Engel SR, Hardy LW, Koch P, Campbell JE, "Cycloalkylamines as monoamine reuptake inhibitors", published 2007-08-30, assigned to Sepracor Inc. 
Asymmetry Patent
  • US patent 7129378, Han X, Krishnamurthy D, Senanayake CH, Lu Z-H, "Method of preparing amine stereoisomers", published 2005-07-28, assigned to Apsinterm LLC