Esreboxetine

Chemical compound
  • None
Legal statusLegal status
  • In general: uncontrolled
Identifiers
  • (2S)-2-[(S)-(2-ethoxyphenoxy)phenyl
    methyl]morpholine
CAS Number
  • 98819-76-2 checkY
PubChem CID
  • 65856
IUPHAR/BPS
  • 4808
ChemSpider
  • 59268 ☒N
UNII
  • L8S50ZY490
KEGG
  • D09340 checkY
CompTox Dashboard (EPA)
  • DTXSID601009938 Edit this at Wikidata
Chemical and physical dataFormulaC19H23NO3Molar mass313.397 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

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]

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

References

  1. ^ a b 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): 1479–1493. doi:10.1517/13543780903203771. PMID 19732029. S2CID 12726987.
  3. ^ "Search of esreboxetine". ClinicalTrials.gov.
  4. ^ Kelly J (26 February 2009). "Pfizer Stops Work on Esreboxetine for FM". Musculoskeletal Report. New York, NY. Archived from the original on 29 February 2012.
  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): 2387–2397. doi:10.1002/art.34390. PMID 22275142.
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
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See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins


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