Esreboxetine

Esreboxetine (developmental code names AXS-14, PNU-165442G) is a selective norepinephrine reuptake inhibitor which was under development by Pfizer for the treatment of neuropathic pain and fibromyalgia but failed to show significant benefit over currently available medications and was discontinued.[1][2][3][4] It is the (S,S)-(+)-enantiomer of reboxetine and is even more selective as a norepinephrine reuptake inhibitor in comparison.[1][5]

Esreboxetine
Clinical data
Other namesAXS-14; PNU-165442G
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • (2S)-2-[(S)-(2-ethoxyphenoxy)phenyl
    methyl]morpholine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO3
Molar mass313.397 g·mol−1
3D model (JSmol)
SMILES
  • CCOC1=CC=CC=C1O[C@H]([C@@H]2CNCCO2)C3=CC=CC=C3
InChI
  • InChI=1S/C19H23NO3/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18/h3-11,18-20H,2,12-14H2,1H3/t18-,19-/m0/s1 N
  • Key:CBQGYUDMJHNJBX-OALUTQOASA-N N
 NY (what is this?)  (verify)

However, recently it has been found that esreboxetine could be effective in fibromyalgia patients.[6]

References
  1. Bingham M, Napier SJ (2009). Transporters as Targets for Drugs (Topics in Medicinal Chemistry). Berlin: Springer. ISBN 978-3-540-87911-4.
  2. Rao SG (October 2009). "Current progress in the pharmacological therapy of fibromyalgia". Expert Opinion on Investigational Drugs. 18 (10): 1479–93. doi:10.1517/13543780903203771. PMID 19732029. S2CID 12726987.
  3. "Search of esreboxetine". ClinicalTrials.gov.
  4. "Musculoskeletal Report: Pfizer Stops Work on Esreboxetine for FM".
  5. Fish PV, Mackenny M, Bish G, Buxton T, Cave R, Drouard D, et al. (2009). "Enantioselective synthesis of (R)- and (S)-N-Boc-morpholine-2-carboxylic acids by enzyme-catalyzed kinetic resolution: application to the synthesis of reboxetine analogs". Tetrahedron Letters. 50 (4): 389–391. doi:10.1016/j.tetlet.2008.11.025.
  6. Arnold LM, Hirsch I, Sanders P, Ellis A, Hughes B (July 2012). "Safety and efficacy of esreboxetine in patients with fibromyalgia: a fourteen-week, randomized, double-blind, placebo-controlled, multicenter clinical trial". Arthritis and Rheumatism. 64 (7): 2387–97. doi:10.1002/art.34390. PMID 22275142.
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