Trifluperidol: Difference between revisions

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{{Drugbox|
{{Drugbox
| IUPAC_name = ''1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]-1-piperidyl]butan-1-one''
| Verifiedfields = changed
| verifiedrevid = 470614624
| IUPAC_name = 1-(4-fluorophenyl)- 4-{4-hydroxy- 4-[3-(trifluoromethyl)phenyl] piperidin-1-yl} butan-1-one
| image = Trifluperidol.svg
| image = Trifluperidol.svg
| width = 200
| width = 200
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|trifluperidol}}
| pregnancy_AU = 
| pregnancy_US = 
| legal_status = 
| routes_of_administration = Oral
<!--Pharmacokinetic data-->
| bioavailability = 
| metabolism = 
| elimination_half-life = 
| excretion = 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 749-13-3
| CAS_number = 749-13-3
| ATC_prefix = N05
| ATC_prefix = N05
| ATC_suffix = AD02  
| ATC_suffix = AD02
| ATC_supplemental =  
| ATC_supplemental =
| PubChem = 5567
| PubChem = 5567
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 22 | H = 23 | F = 4 | N = 1 || O = 2
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5366
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R8869Q7R8I
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15023
 
<!--Chemical data-->
| C=22 | H=23 | F=4 | N=1 | O=2  
| molecular_weight = 409.417 g/mol
| molecular_weight = 409.417 g/mol
| bioavailability =  
| smiles = FC(F)(F)c1cccc(c1)C3(O)CCN(CCCC(=O)c2ccc(F)cc2)CC3
| metabolism =  
| InChI = 1/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2
| elimination_half-life =
| InChIKey = GPMXUUPHFNMNDH-UHFFFAOYAW
| excretion =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_AU =  
| StdInChI = 1S/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2
| pregnancy_US =  
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| legal_status =
| StdInChIKey = GPMXUUPHFNMNDH-UHFFFAOYSA-N
| routes_of_administration = Oral
}}
}}
'''Trifluperidol''' is a [[drug]] which is a [[butyrophenone]] [[derivative (chemistry)|derivative]]. It has general properties similar to those of [[haloperidol]], but is considerably more potent by weight, and causes relatively more severe side effects, especially [[tardive dyskinesia]] and other [[extrapyramidal]] effects. It is used in the treatment of psychoses including [[mania]] and [[schizophrenia]].


Trifluperidol was discovered at [[Janssen Pharmaceutica]] in [[1959]].
'''Trifluperidol''' is a [[typical antipsychotic]] of the [[butyrophenone]] [[chemical class]]. It has general properties similar to those of [[haloperidol]], but is considerably more potent by weight, and causes relatively more severe side effects, especially [[tardive dyskinesia]] and other [[extrapyramidal symptoms|extrapyramidal]] effects. It is used in the treatment of psychoses including [[mania]] and [[schizophrenia]]. It was discovered at [[Janssen Pharmaceutica]] in 1959.


==References==
==Synthesis==
[[File:Trifluperidol Synthesis.png|500px|center|thumb|Trifluperidol Synthesis: P. Janssen, J. Adriaan, {{Cite patent|GB|895309}} (1962), {{US Patent|3438991}} (1969).]]
== References ==
{{Reflist|2}}
* Gallant DM, Bishop MP, Timmons E, Steele CA, A controlled evaluation of Trifluperidol: a new potent psychopharmacologic agent, Curr Ther Res Clin Exp. 1963 Sep;27:463-71.
* Gallant DM, Bishop MP, Timmons E, Steele CA, A controlled evaluation of Trifluperidol: a new potent psychopharmacologic agent, Curr Ther Res Clin Exp. 1963 Sep;27:463-71.
* Gallant DM, Bishop MP, Timmons E, Steele CA, Trifluperidol: a butyrophenone derivative, Am J Psychiatry. 1963 Nov;120:485-7.
* Gallant DM, Bishop MP, Timmons E, Steele CA, Trifluperidol: a butyrophenone derivative, Am J Psychiatry. 1963 Nov;120:485-7.


{{Antipsychotics}}
{{Dopaminergics}}


{{pharma-stub}}
[[Category:Piperidines]]
[[Category:Organofluorides]]
[[Category:Aromatic ketones]]
[[Category:Alcohols]]
[[Category:Butyrophenone antipsychotics]]
[[Category:Janssen Pharmaceutica]]
[[Category:Belgian inventions]]


{{Antipsychotics}}


[[Category:Typical antipsychotics]]
{{nervous-system-drug-stub}}

Revision as of 13:07, 10 April 2015

{{Drugbox | Verifiedfields = changed | verifiedrevid = 470614624 | IUPAC_name = 1-(4-fluorophenyl)- 4-{4-hydroxy- 4-[3-(trifluoromethyl)phenyl] piperidin-1-yl} butan-1-one | image = Trifluperidol.svg | width = 200

| tradename = | Drugs.com = International Drug Names | pregnancy_AU = | pregnancy_US = | legal_status = | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref =  ☒N | CAS_number = 749-13-3 | ATC_prefix = N05 | ATC_suffix = AD02 | ATC_supplemental = | PubChem = 5567 | DrugBank_Ref =  ☑Y | DrugBank = | ChemSpiderID_Ref =  ☑Y | ChemSpiderID = 5366 | UNII_Ref =  ☑Y | UNII = R8869Q7R8I | ChEMBL_Ref =  ☑Y | ChEMBL = 15023

| C=22 | H=23 | F=4 | N=1 | O=2 | molecular_weight = 409.417 g/mol | smiles = FC(F)(F)c1cccc(c1)C3(O)CCN(CCCC(=O)c2ccc(F)cc2)CC3 | InChI = 1/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2 | InChIKey = GPMXUUPHFNMNDH-UHFFFAOYAW | StdInChI_Ref =  ☑Y | StdInChI = 1S/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2 | StdInChIKey_Ref =  ☑Y | StdInChIKey = GPMXUUPHFNMNDH-UHFFFAOYSA-N }}

Trifluperidol is a typical antipsychotic of the butyrophenone chemical class. It has general properties similar to those of haloperidol, but is considerably more potent by weight, and causes relatively more severe side effects, especially tardive dyskinesia and other extrapyramidal effects. It is used in the treatment of psychoses including mania and schizophrenia. It was discovered at Janssen Pharmaceutica in 1959.

Synthesis

Trifluperidol Synthesis: P. Janssen, J. Adriaan, GB 895309  (1962), Template:US Patent (1969).

References

  • Gallant DM, Bishop MP, Timmons E, Steele CA, A controlled evaluation of Trifluperidol: a new potent psychopharmacologic agent, Curr Ther Res Clin Exp. 1963 Sep;27:463-71.
  • Gallant DM, Bishop MP, Timmons E, Steele CA, Trifluperidol: a butyrophenone derivative, Am J Psychiatry. 1963 Nov;120:485-7.


Template:Nervous-system-drug-stub

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