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Esreboxetine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Esreboxetine
Clinical data
Other namesAXS-14; PNU-165442G
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (2S)-2-[(S)-(2-ethoxyphenoxy)phenyl
    methyl]morpholine
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H23NO3
Molar mass313.397 g·mol−1
3D model (JSmol)
  • CCOC1=CC=CC=C1O[C@H]([C@@H]2CNCCO2)C3=CC=CC=C3
  • 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 namesAXS-14, PNU-165442G) is aselectivenorepinephrine reuptake inhibitor which was under development byPfizer for the treatment ofneuropathic pain andfibromyalgia but failed to show significant benefit over currently available medications and was discontinued.[1][2][3][4] It is the (S,S)-(+)-enantiomer ofreboxetine 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

[edit]
  1. ^abBingham 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 fromthe 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)
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