Flufenoxine

Flufenoxine
Clinical data
Other names	F-98214-TA
Identifiers
	IUPAC name 4-[(3-fluorophenoxy)-phenylmethyl]piperidine;
CAS Number	957202-15-2;
PubChem CID	9817317;
ChemSpider	7993067;
ChEMBL	ChEMBL152935;
Chemical and physical data
Formula	C18H20FNO
Molar mass	285.362 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CNCCC1C(C2=CC=CC=C2)OC3=CC(=CC=C3)F;
	InChI InChI=1S/C18H20FNO/c19-16-7-4-8-17(13-16)21-18(14-5-2-1-3-6-14)15-9-11-20-12-10-15/h1-8,13,15,18,20H,9-12H2; Key:FDHPZDXAAGIHFC-UHFFFAOYSA-N;

Flufenoxine (F-98214-TA) is a Serotonin–norepinephrine reuptake inhibitor. It can be used to treat disorders of the central nervous system, particularly depression and anxiety. It was developed by a Spanish company at the beginning of the 21st century.^[1]

Flufenoxine derivatives have been patented for the treatment of Alzheimer's disease.^[2]

Analogues of Flufenoxine were reported containing a duloxetine-type thiophene surrogate ring moiety.^[3] Such agents possess the desired triple-mode of activity (serotonin-noradrenaline and dopamine) (cf. SNDRI).

For another related SNDRI agent see PC71812205. The racemic agent had IC50's of 11, 14, 190nM S~N>D.^[4]^[5]

References

^ Artaiz I, Zazpe A, Innerárity A, Del Olmo E, Díaz A, Ruiz-Ortega JA, et al. (November 2005). "Preclinical pharmacology of F-98214-TA, a novel potent serotonin and norepinephrine uptake inhibitor with antidepressant and anxiolytic properties". Psychopharmacology. 182 (3): 400–13. doi:10.1007/s00213-005-0087-3. PMID 16032410.
^ Francisco Ledo Gómez, et al. WO2011147780 (Fabrica Espanola de Productos Quimicos y Farmaceuticos FAES SA).
^ 郭强, et al. WO2015131814 (to WUHAN JIAYU TECHNOLOGY Co Ltd, Nhwa Pharmaceutical Corp).
^ Ishichi, Yuji; Kimura, Eiji; Honda, Eiji; Yoshikawa, Masato; Nakahata, Takashi; Terao, Yasuko; Suzuki, Atsuko; Kawai, Takayuki; Arakawa, Yuuichi; Ohta, Hiroyuki; Kanzaki, Naoyuki; Nak-agawa, Hideyuki; Terauchi, Jun (2013). "Novel triple reuptake inhibitors with low risk of CAD associated liabilities: Design, synthesis and biological activities of 4-[(1S)-1-(3,4-dichlorophenyl)-2-methoxyethyl]piperidine and related compounds". Bioorganic & Medicinal Chemistry. 21 (15): 4600–4613. doi:10.1016/j.bmc.2013.05.025.
^ Ishichi Yuji, Kimura Eiji &Terauchi Jun, WO2010016554 (to Takeda).

[pmid16032410-1] Artaiz I, Zazpe A, Innerárity A, Del Olmo E, Díaz A, Ruiz-Ortega JA, et al. (November 2005). "Preclinical pharmacology of F-98214-TA, a novel potent serotonin and norepinephrine uptake inhibitor with antidepressant and anxiolytic properties". Psychopharmacology. 182 (3): 400–13. doi:10.1007/s00213-005-0087-3. PMID 16032410.

[2] Francisco Ledo Gómez, et al. WO2011147780 (Fabrica Espanola de Productos Quimicos y Farmaceuticos FAES SA).

[3] 郭强, et al. WO2015131814 (to WUHAN JIAYU TECHNOLOGY Co Ltd, Nhwa Pharmaceutical Corp).

[4] Ishichi, Yuji; Kimura, Eiji; Honda, Eiji; Yoshikawa, Masato; Nakahata, Takashi; Terao, Yasuko; Suzuki, Atsuko; Kawai, Takayuki; Arakawa, Yuuichi; Ohta, Hiroyuki; Kanzaki, Naoyuki; Nak-agawa, Hideyuki; Terauchi, Jun (2013). "Novel triple reuptake inhibitors with low risk of CAD associated liabilities: Design, synthesis and biological activities of 4-[(1S)-1-(3,4-dichlorophenyl)-2-methoxyethyl]piperidine and related compounds". Bioorganic & Medicinal Chemistry. 21 (15): 4600–4613. doi:10.1016/j.bmc.2013.05.025.

[5] Ishichi Yuji, Kimura Eiji &Terauchi Jun, WO2010016554 (to Takeda).

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