4189. Fluphenazine

Nomenclature

CAS number: 69-23-8
4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol; 1-(2-hydroxyethyl)-4-[3-(trifluoromethyl-10-phenothiazinyl)propyl]piperazine; 10-[3′-[4″-(β-hydroxyethyl)-1″-piperazinyl]propyl]-3-trifluoromethylphenothiazine; 2-(trifluoromethyl)-10-[3-[1-(β-hydroxyethyl)-4-piperazinyl]propyl]phenothiazine; S-94; SQ-4918.
C22H26F3N3OS; mol wt 437.52.
C 60.39%, H 5.99%, F 13.03%, N 9.60%, O 3.66%, S 7.33%.

Description and references

Prepn: H. L. Yale, F. Sowinski, J. Am. Chem. Soc. 82, 2039 (1960); GB 829246; G. E. Ullyot, US 3058979 (1960, 1962 both to SKF); GB 833474 (1960 to Scherico), C.A. 54, 21143e (1960); E. L. Anderson et al., Arzneim.-Forsch. 12, 937 (1962); H. L. Yale, R. C. Merrill, US 3194733 (1965 to Olin Mathieson). Metabolism: J. Dreyfuss, A. J. Cohen, J. Pharm. Sci. 60, 826 (1971). Comprehensive description of the enanthate ester: K. Florey, Anal. Profiles Drug Subs. 2, 245-262 (1973); of the dihydrochloride: idem, ibid. 263-294; of the decanoate ester: G. Clarke, ibid. 9, 275-294 (1980).

Chemical structure

Properties

Dark brown viscous oil, bp0.5 268-274°; bp0.3 250-252°.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 146-56-5
Anatensol (BMS); Dapotum (BMS); Lyogen (Promonta Lundbeck); Moditen (Sanofi Winthrop); Omca (BMS); Pacinol (Schering); Permitil (Schering); Prolixin (Apothecon); Siqualone (BMS); Tensofin (BMS); Valamina (Schering).
C22H26F3N3OS.2HCl; mol wt 510.44.
C 51.77%, H 5.53%, F 11.17%, N 8.23%, O 3.13%, S 6.28%, Cl 13.89%.

Properties

Crystals from abs ethanol, mp 235-237°. Also reported as mp 224.5-226°.

Derivative

Decanoate.

Nomenclature

CAS number: 5002-47-1
SQ-10733; QD-10733; Modecate (Sanofi Winthrop).
C32H44F3N3O2S; mol wt 591.77.
C 64.95%, H 7.49%, F 9.63%, N 7.10%, O 5.41%, S 5.42%.

Properties

Pale yellow-orange, viscous liquid. Slowly crystallizes at room temp. mp 30-32°. Very sol in chloroform, ether, cyclohexane, methanol, ethanol. Insol in water.

Derivative

Enanthate.

Nomenclature

CAS number: 2746-81-8
SQ-16144.
C29H38F3N3O2S; mol wt 549.69.
C 63.36%, H 6.97%, F 10.37%, N 7.64%, O 5.82%, S 5.83%.

Properties

Pale yellow to yellow-orange viscous liquid or oily solid.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Phenothiazines