Clofuperol

Clofluperol
Clinical data
Other names	Seperidol, R9298
Identifiers
	IUPAC name 4-[4-[4-chloro-3-(trifluoromethyl)phenyl]-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one;
CAS Number	10457-91-7;
PubChem CID	25293;
ChemSpider	23626;
UNII	N57F04DIDQ;
ChEMBL	ChEMBL2111071;
CompTox Dashboard (EPA)	DTXSID90146562 ;
Chemical and physical data
Formula	C22H22ClF4NO2
Molar mass	443.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCC1(C2=CC(=C(C=C2)Cl)C(F)(F)F)O)CCCC(=O)C3=CC=C(C=C3)F;
	InChI InChI=1S/C22H22ClF4NO2/c23-19-8-5-16(14-18(19)22(25,26)27)21(30)9-12-28(13-10-21)11-1-2-20(29)15-3-6-17(24)7-4-15/h3-8,14,30H,1-2,9-13H2; Key:LZFSKNPPWIFMFL-UHFFFAOYSA-N;

Clofluperol is a neuroleptic tranquilizer of the butyrophenone class.^[1]^[2]^[3] It has the same aromatic piperidinol moiety that is present in penfluridol and fluperamide. The structure can be seen to be a sort of hybrid between that of trifluperidol and haloperidol.

References

^ Bobon J, Pinchard A, Goffioul F, Devroye A, Bobon DP, Korn M (February 1968). "[Long-acting neuroleptics. I. Pilot study of clofluperol (R9298)]". Acta Neurologica et Psychiatrica Belgica (in French). 68 (2): 128–136. PMID 4972601.
^ Janssen PA, Allewijn FT (February 1969). "The distribution of the butyrophenones haloperidol, trifluperidol, moperone, and clofluperol in rats, and its relationship with their neuroleptic activity". Arzneimittel-Forschung. 19 (2): 199–208. PMID 5818759.
^ Mishkinsky J, Khazen K, Givant Y, Dikstein S (May 1969). "Sulman FG: Mammotropic and neuroleptic effects of butyrophenones in the rat". Archives Internationales de Pharmacodynamie et de Therapie. 179 (1): 94–105. PMID 5388566.

[Bobon_1968-1] Bobon J, Pinchard A, Goffioul F, Devroye A, Bobon DP, Korn M (February 1968). "[Long-acting neuroleptics. I. Pilot study of clofluperol (R9298)]". Acta Neurologica et Psychiatrica Belgica (in French). 68 (2): 128–136. PMID 4972601.

[Janssen_1969-2] Janssen PA, Allewijn FT (February 1969). "The distribution of the butyrophenones haloperidol, trifluperidol, moperone, and clofluperol in rats, and its relationship with their neuroleptic activity". Arzneimittel-Forschung. 19 (2): 199–208. PMID 5818759.

[Mishkinsky_1969-3] Mishkinsky J, Khazen K, Givant Y, Dikstein S (May 1969). "Sulman FG: Mammotropic and neuroleptic effects of butyrophenones in the rat". Archives Internationales de Pharmacodynamie et de Therapie. 179 (1): 94–105. PMID 5388566.

[1]

[2]

[3]

v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Muscarinic agonists: Xanomeline/trospium chloride Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III