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Femoxetine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Femoxetine
Clinical data
Routes of
administration
Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Eliminationhalf-life7–27 hours
Identifiers
  • (3R,4S)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenyl-piperidine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H25NO2
Molar mass311.425 g·mol−1
3D model (JSmol)
  • O(c1ccc(OC)cc1)C[C@@H]3[C@@H](c2ccccc2)CCN(C)C3
  • InChI=1S/C20H25NO2/c1-21-13-12-20(16-6-4-3-5-7-16)17(14-21)15-23-19-10-8-18(22-2)9-11-19/h3-11,17,20H,12-15H2,1-2H3/t17-,20-/m1/s1 checkY
  • Key:OJSFTALXCYKKFQ-YLJYHZDGSA-N checkY
  (verify)

Femoxetine (INN; tentative brand nameMalexil; developmental code nameFG-4963) is adrug related toparoxetine that was being developed as anantidepressant by Danishpharmaceutical company Ferrosan in 1975 before acquisition of the company byNovo Nordisk. It acts as aselective serotonin reuptake inhibitor (SSRI). Development was halted to focus attention onparoxetine instead, as femoxetine could not be administered as a daily pill.

Both femoxetine and paroxetine were invented in the 1970s. Jørgen Anders Christensen's name is on the patents[1][2] and Jorgen Buus-Lassen's name is on the pharmacologypaper.[3]

After Ferrosan's acquisition, femoxetine died from neglect.[4]

In a separate patent, Ferrosan stated that Femoxetine could be used as an appetite suppressant,[5] using ten times the dosage than for paroxetine, 300 - 400mg daily.

Femoxetine has the same stereochemical properties asNocaine, another agent with a similar structure claimed to have been synthesized usingarecoline as the starting alkaloid.[citation needed]

Analogs

[edit]
This sectionmay be too technical for most readers to understand. Pleasehelp improve it tomake it understandable to non-experts, without removing the technical details.(March 2022) (Learn how and when to remove this message)
  1. Addition of thepara-fluoro atom results in a different compound that is a hybrid of femoxetine & paroxetine named FG 7080,[6] which has a separate patent.[7] According to the patent tables, incorporation of the fluorine atom potentiated the 5-HT affinity considerably.
  2. Pfizer made some similar analogs[8] E.g. aViloxazine type of catechol ether is used, but 4-phenyl instead of based on a morpholine ring.
  3. NNC-63-0780.[9][10] binds toORL1 instead ofSERT.
  • NNC 09-0026

See also

[edit]

References

[edit]
  1. ^U.S. patent 3,912,743
  2. ^U.S. patent 4,007,196
  3. ^Lassen JB, Petersen E, Kjellberg B, Olsson SO (May 1975). "Comparative studies of a new 5HT-uptake inhibitor and some tricyclic thymoleptics".European Journal of Pharmacology.32 (1):108–15.doi:10.1016/0014-2999(75)90329-5.PMID 1149822.
  4. ^Healy D (2004).Let them eat Prozac: the unhealthy relationship between the pharmaceutical industry and depression. New York, NY: New York Univ. Press. pp. 26–27.ISBN 9780814736692.Jørgen Buus Lassen femoxetine.
  5. ^U.S. patent 4,442,113
  6. ^"(3S,4R)-4-(4-Fluorophenyl)-3-[(4-methoxyphenoxy)methyl]piperidine".PubChem. U.S. National Library of Medicine.
  7. ^U.S. patent 4,585,777
  8. ^U.S. patent 20,070,142,389
  9. ^Bignan GC, Connolly PJ, Middleton SA (2005). "Recent advances towards the discovery of ORL-1 receptor agonists and antagonists".Expert Opinion on Therapeutic Patents.15 (4): 357–388 6.doi:10.1517/13543776.15.4.357.S2CID 94720416.
  10. ^"CID:9862655".PubChem. U.S. National Library of Medicine.
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
Others
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
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