Fluacizine

Fluacizine, sold under the brand name Phtorazisin, is a tricyclic antidepressant (TCA) of the phenothiazine group which is or was marketed in Russia.[1][2][3] Unlike other phenothiazines, fluacizine is not an antipsychotic, and can actually reverse catalepsy and extrapyramidal symptoms induced by antidopaminergic agents like antipsychotics, reserpine, and tetrabenazine as well as potentiate amphetamine-induced stereotypy.[3] It is known to act as a norepinephrine reuptake inhibitor, antihistamine, and anticholinergic.[4][5][6][7][3] The drug was developed in the 1960s and was marketed in the 1970s.[1][4] It is the trifluoromethyl analogue of chloracizine.[7]

Fluacizine
Clinical data
Trade namesPhtorazisin
Other namesFluoracizine; Fluoracyzine; Fluoracisine; Ftoracizin; Ftoracizine; Phthoracizin[1][2]
Routes of
administration		Oral, intramuscular injection
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 3-Diethylamino-1-[2-(trifluoromethyl)phenothiazin-10-yl]-propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21F3N2OS
Molar mass394.46 g·mol−1
3D model (JSmol)
SMILES
  • FC(F)(F)c2cc1N(c3c(Sc1cc2)cccc3)C(=O)CCN(CC)CC
InChI
  • InChI=1S/C20H21F3N2OS/c1-3-24(4-2)12-11-19(26)25-15-7-5-6-8-17(15)27-18-10-9-14(13-16(18)25)20(21,22)23/h5-10,13H,3-4,11-12H2,1-2H3 Y
  • Key:VHEOUJNDDFHPGJ-UHFFFAOYSA-N Y
  (verify)

Synthesis
Synthesis:[8] Patents:[9][10][11][12] Use as antidepressant:[13]

2-(Trifluoromethyl)Phenothiazine [92-30-8] (1) is acylated with 3-Chloropropionyl Chloride [625-36-5] (2) to give 3-chloro-1-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propan-1-one [27312-94-3] (3). Displacement of the terminal ω-halogen in the sidechain with diethylamine (4) completed the synthesis of Fluacizine (5).

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 555–. ISBN 978-1-4757-2085-3.
  2. O'Neil, Maryadele J. (2001). The Merck index: an encyclopedia of chemicals, drugs, and biologicals. Rahway, NJ: Merck Research Laboratories. ISBN 0-911910-13-1.
  3. V. V. Zakusov (22 October 2013). Pharmacology of Central Synapses. Elsevier. pp. 190–. ISBN 978-1-4831-4673-7.
  4. Arefolov VA, Panasyuk LV, Raevskii KS, Kostyukov VI (1974). "Effect of fluacizine on the uptake of exogenous noradrenalin by the isolated rat vas deferens". Bull. Exp. Biol. Med. 77 (3): 295–7. doi:10.1007/BF00802484. PMID 4153328. S2CID 13188296.
  5. Arefolov VA, Panasyuk LV (1974). "Effect of fluacizine on the uptake of exogenous noradrenalin". Bull. Exp. Biol. Med. 77 (5): 520–3. doi:10.1007/BF00797411. PMID 4441683. S2CID 27205700.
  6. Arefolov VA, Panasiuk LV, Firsov VK (1975). "[Neuromediator content in the synaptic vesicles of rat adrenergic nerves in some pharmacological actions]". Farmakol Toksikol (in Russian). 38 (3): 285–9. PMID 6305.
  7. Annual Reports in Medicinal Chemistry. Academic Press. 27 October 1972. pp. 19–. ISBN 978-0-08-058351-8.
  8. Gritsenko, A.N. et al, Khim.-Farm. Zh., 1971,5, 18.
  9. Y. I. Vikhlyaev et al., SU360342 (1972), C.A.78, 97683w (1973).
  10. S. V. Zhuravlev et al., GB 1191800 (1970), C.A. 73, 25493h (1970).
  11. Y. I. Vikhlyaev et al., FR 2035748 (1971), C.A. 75, 140872j (1971).
  12. Bichljajew Jurij I, Grisenko Anna N, Surawlew Semen W, Klygul Tatjana A, Uljanowa Olga W, DE 1805659A1 (1971 to Nii Farmakologij I Chimoterapi), C.A. 75, 49101w (1971).
  13. SU356992 (1972), C.A. 78, 75888q (1973) (all to Inst. Pharmacol. Chemother., Acad. Med. Sci., USSR).


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