Femoxetine Routes of administration Oral ATC code Legal status
Elimination half-life 7–27 hours
(3R ,4S )-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenyl-piperidine
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) Formula C 20 H 25 N O 2 Molar mass 311.425 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
Y Key:OJSFTALXCYKKFQ-YLJYHZDGSA-N
Y
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 by Novo Nordisk . It acts as a selective serotonin reuptake inhibitor (SSRI). Development was halted to focus attention on paroxetine instead, given femoxetine's inability to be administered as a daily pill.
Both femoxetine and paroxetine were invented in the 1970s by Jorgen Buus-Lassen (Jørgen Anders Christensen name on the patents though).[1] [2] Jorgen Buus-Lassen's name is on the pharmacology paper, however.[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] The dosage was 10 times more highly generous than for paroxetine, i.e. 300 - 400mg / day.
Femoxetine still does possess the same stereochemical properties as Nocaine , another agent claimed to have been synthesized using arecoline as the starting alkaloid.
Analogs [ ]
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.
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.
NNC-63-0780.[9] [10] binds to ORL1 instead of SERT .
See also [ ]
References [ ]
^ U.S. Patent 3,912,743
^ U.S. Patent 4,007,196
^ 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 .
^ 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.
^ U.S. Patent 4,442,113
^ "(3S,4R)-4-(4-Fluorophenyl)-3-[(4-methoxyphenoxy)methyl]piperidine" . PubChem . U.S. National Library of Medicine.
^ U.S. Patent 4,585,777
^ U.S. Patent 20,070,142,389
^ 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 .
^ "CID:9862655" . PubChem . U.S. National Library of Medicine.
Monoamine reuptake inhibitors
DAT (DRIs )
Piperazines: DBL-583
GBR-12783
GBR-12935
GBR-13069
GBR-13098
Nefazodone
Vanoxerine
Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone
NET (NRIs )
Tricyclic antidepressants: Amitriptyline
Butriptyline
Cianopramine
Clomipramine
Desipramine
Dosulepin (dothiepin)
Doxepin
Imipramine
Lofepramine
Melitracen
Nortriptyline
Protriptyline
Trimipramine
Tetracyclic antidepressants: Amoxapine
Maprotiline
Mianserin
Oxaprotiline
Setiptiline
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., ketamine , phencyclidine )
Dopexamine
Ephenidine
Ginkgo biloba
Indeloxazine
Nefazodone
Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT (SRIs )
Tricyclic antidepressants: Amitriptyline
Cianopramine
Clomipramine
Cyanodothiepin
Desipramine
Dosulepin (dothiepin)
Doxepin
Imipramine
Lofepramine
Nortriptyline
Pipofezine
Protriptyline
Others:
Amoxapine
Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )
Cyclobenzaprine
Delucemine
Dextromethorphan
Dextrorphan
Efavirenz
Hypidone
Medifoxamine
Mesembrine
Mifepristone
MIN-117 (WF-516)
N-Me-5-HT
Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )
Roxindole
VMATs
Amiodarone
Amphetamines (e.g., amphetamine , methamphetamine , MDMA )
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
Ibogaine
Ketanserin
Lobeline
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)
Others
DAT modulators: Agonist-like: SoRI-9804
; Antagonist-like: SoRI-20041
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
mAChRs
Agonists Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (+formoterol )
Abediterol
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g., brompheniramine , buclizine , captodiame , chlorphenamine (chlorpheniramine) , cinnarizine , clemastine , cyproheptadine , dimenhydrinate , dimetindene , diphenhydramine , doxylamine , meclizine , mequitazine , perlapine , phenindamine , pheniramine , phenyltoloxamine , promethazine , propiomazine , triprolidine )
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g., clozapine , fluperlapine , olanzapine (+fluoxetine ), , quetiapine , tenilapine , zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
Desfesoterodine
Dexetimide
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (+beclometasone/formoterol , +indacaterol )
Hexocyclium
Himbacine
Homatropine
Imidafenacin
Ipratropium bromide (+salbutamol )
Isopropamide
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PD-102,807
PD-0298029
Penthienate
Pethidine
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Sofpironium bromide
Solifenacin
SSRIs (e.g., femoxetine , paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g., amitriptyline (+perphenazine ), amitriptylinoxide , butriptyline , cidoxepin , clomipramine , desipramine , , dibenzepin , dosulepin (dothiepin) , doxepin , imipramine , lofepramine , nitroxazepine , northiaden (desmethyldosulepin) , nortriptyline , protriptyline , quinupramine , trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g., chlorpromazine , chlorprothixene , cyamemazine (cyamepromazine) , loxapine , mesoridazine , thioridazine )
Umeclidinium bromide (+vilanterol )
WIN-2299
Xanomeline
Precursors (and prodrugs )
Acetyl-coA
Adafenoxate
Choline (lecithin )
Citicoline
Cyprodenate
Dimethylethanolamine
Glycerophosphocholine
Meclofenoxate (centrophenoxine)
Phosphatidylcholine
Phosphatidylethanolamine
Phosphorylcholine
Pirisudanol
See also: Receptor/signaling modulators • Nicotinic acetylcholine receptor modulators • Acetylcholine metabolism/transport modulators