Femoxetine

Femoxetine (INN; tentative brand name Malexil; developmental code name FG-4963) is a drug related to paroxetine that was being developed as an antidepressant by Danish pharmaceutical company Ferrosan in 1975 before acquisition of the company by Novo Nordisk. It acts as a selective serotonin reuptake inhibitor (SSRI). Development was halted to focus attention on paroxetine instead, as femoxetine could not be administered as a daily pill.

Femoxetine
Clinical data
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Elimination half-life7–27 hours
Identifiers
IUPAC name
  • (3R,4S)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenyl-piperidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H25NO2
Molar mass311.425 g·mol−1
3D model (JSmol)
SMILES
  • O(c1ccc(OC)cc1)C[C@@H]3[C@@H](c2ccccc2)CCN(C)C3
InChI
  • 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 Y
  • Key:OJSFTALXCYKKFQ-YLJYHZDGSA-N Y
  (verify)

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 pharmacology paper.[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 as Nocaine, another agent with a similar structure claimed to have been synthesized using arecoline as the starting alkaloid.

Analogs
  1. Addition of the para-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. a Viloxazine type of catechol ether is used, but 4-phenyl instead of based on a morpholine ring.
  3. NNC-63-0780.[9][10] binds to ORL1 instead of SERT.
  • NNC 09-0026

See also

References
  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.
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