Fluphenazine

Title: Fluphenazine
CAS Registry Number: 69-23-8
CAS Name: 4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol
Additional Names: 1-(2-hydroxyethyl)-4-[3-(trifluoromethyl-10-phenothiazinyl)propyl]piperazine; 10-[3¢-[4¢¢-(b-hydroxyethyl)-1¢¢-piperazinyl]propyl]-3-trifluoromethylphenothiazine; 2-(trifluoromethyl)-10-[3-[1-(b-hydroxyethyl)-4-piperazinyl]propyl]phenothiazine
Manufacturers' Codes: S-94; SQ-4918
Molecular Formula: C22H26F3N3OS
Molecular Weight: 437.52
Percent Composition: C 60.39%, H 5.99%, F 13.03%, N 9.60%, O 3.66%, S 7.33%
Literature 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).
Properties: Dark brown viscous oil, bp0.5 268-274°; bp0.3 250-252°.
Boiling point: bp0.5 268-274°; bp0.3 250-252°
Derivative Type: Dihydrochloride
CAS Registry Number: 146-56-5
Trademarks: Anatensol (BMS); Dapotum (BMS); Lyogen (Promonta Lundbeck); Moditen (Sanofi Winthrop); Omca (BMS); Pacinol (Schering); Permitil (Schering); Prolixin (Apothecon); Siqualone (BMS); Tensofin (BMS); Valamina (Schering)
Molecular Formula: C22H26F3N3OS.2HCl
Molecular Weight: 510.44
Percent Composition: 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°.
Melting point: mp 235-237°; Also reported as mp 224.5-226°
Derivative Type: Decanoate
CAS Registry Number: 5002-47-1
Manufacturers' Codes: SQ-10733; QD-10733
Trademarks: Modecate (Sanofi Winthrop)
Molecular Formula: C32H44F3N3O2S
Molecular Weight: 591.77
Percent Composition: 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.
Melting point: mp 30-32°
Derivative Type: Enanthate
CAS Registry Number: 2746-81-8
Manufacturers' Codes: SQ-16144
Molecular Formula: C29H38F3N3O2S
Molecular Weight: 549.69
Percent Composition: 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.
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Phenothiazines.
Flupirtine Fluprednidene Acetate Fluprednisolone Fluproquazone Fluprostenol

Fluphenazine
Systematic (IUPAC) name
2-[4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol
Clinical data
Trade names Prolixin
AHFS/Drugs.com monograph
MedlinePlus a682172
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes oral, IM, decanoate
Pharmacokinetic data
Bioavailability 2.7% (Oral)
Metabolism Hepatic
Half-life 33 hours
Excretion bile/feces
Identifiers
CAS number 69-23-8 YesY
ATC code N05AB02
PubChem CID 3372
IUPHAR ligand 204
DrugBank DB00623
ChemSpider 3255 YesY
UNII S79426A41Z YesY
KEGG D07977 YesY
ChEBI CHEBI:5123 YesY
ChEMBL CHEMBL726 YesY
Chemical data
Formula C22H26F3N3OS 
Mol. mass 437.523 g/mol
 YesY (what is this?)  (verify)

Fluphenazine is a typical antipsychotic drug used for the treatment of psychoses such as schizophrenia, manic phases of bipolar disorder, agitation, and dementia. It belongs to the piperazine class of phenothiazines. The medication may help control symptoms by blocking or lessening the effects of dopamine in the brain. It is not entirely known how the medication works. Dopamine may be elevated in people with schizophrenia or other psychoses. It also can be used as a calming drug in horses, though such use is illegal.

The medication was originally manufactured by Bristol-Myers Squibb. It is currently marketed under the brand name Modecate, a number of generic versions are also available. It is made by several different companies. The medication comes in oral liquid, tablets (1mg, 2.5mg, 5mg, 10mg), and injectable forms (including a short-acting and long-acting form).

Its side effect profile is similar to haloperidol, namely predominantly dopamine-blocking effects, which give rise to akathisia, parkinsonism, and tremor. Long term side effects include the potentially irreversible tardive dyskinesia and the potentially fatal neuroleptic malignant syndrome.