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Femoxetine

Clinical data
Routes of administration	Oral
ATC code	None
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Elimination half-life	7–27 hours
Identifiers
IUPAC name (3R,4S)-3--1-methyl-4-phenyl-piperidine
CAS Number	59859-58-4
PubChem CID	3012003
ChemSpider	2280941
UNII	8Y719ZLX8C
ChEMBL	ChEMBL94739
CompTox Dashboard (EPA)	DTXSID70208576
Chemical and physical data
Formula	C20H25NO2
Molar mass	311.425 g·mol
3D model (JSmol)	Interactive image
SMILES O(c1ccc(OC)cc1)C3(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 Key:OJSFTALXCYKKFQ-YLJYHZDGSA-N
(verify)

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.

Both femoxetine and paroxetine were invented in the 1970s. Jørgen Anders Christensen's name is on the patents and Jorgen Buus-Lassen's name is on the pharmacology paper.

After Ferrosan's acquisition, femoxetine died from neglect.

In a separate patent, Ferrosan stated that Femoxetine could be used as an appetite suppressant, 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

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1. Addition of the para-fluoro atom results in a different compound that is a hybrid of femoxetine & paroxetine named FG 7080, which has a separate patent. According to the patent tables, incorporation of the fluorine atom potentiated the 5-HT affinity considerably.
2. Pfizer made some similar analogs E.g. a Viloxazine type of catechol ether is used, but 4-phenyl instead of based on a morpholine ring.
3. NNC-63-0780. binds to ORL1 instead of SERT.

• NNC 09-0026

See also

• Alaproclate
• Indalpine
• Zimelidine

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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• Drugs not assigned an ATC code
• Antidepressants
• Muscarinic antagonists
• 4-Methoxyphenyl compounds
• 4-Phenylpiperidines
• Selective serotonin reuptake inhibitors
• Abandoned drugs
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