Clocapramine

Clocapramine (Clofekton, Padrasen), also known as 3-chlorocarpipramine, is an atypical antipsychotic of the iminostilbene class which was introduced in Japan in 1974 by Yoshitomi for the treatment of schizophrenia.^{[1][2][3][4][5]} In addition to psychosis, clocapramine has also been used to augment antidepressants in the treatment of anxiety and panic.^[6]

Clocapramine

Clinical data
Trade names	Clofekton, Padrasen
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	None
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-[3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-4-piperidin-1-ylpiperidine-4-carboxamide
CAS Number	47739-98-0
PubChem CID	2793
DrugBank	DB09003 Y
ChemSpider	2691
UNII	6EEL1GB72K
KEGG	D07718
ChEMBL	ChEMBL2104103
CompTox Dashboard (EPA)	DTXSID1057749
Chemical and physical data
Formula	C28H37ClN4O
Molar mass	481.08 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccc3c(c1)N(c2ccccc2CC3)CCCN5CCC(C(=O)N)(N4CCCCC4)CC5

Clocapramine has been reported to act as an antagonist of the D₂, 5-HT_2A, α₁-adrenergic, and α₂-adrenergic receptors, and does not inhibit the reuptake of either serotonin or norepinephrine.^{[4][7][8][9][10]} It has also been shown to have affinity for SIGMAR1.^[11] Clocapramine's affinity for the 5-HT_2A receptor is greater than that for the D₂ receptor and it has a lower propensity for inducing extrapyramidal symptoms compared to typical antipsychotics, thus underlying its atypical nature.^[4][5][10]

Clinical trials

In several clinical trials, clocapramine has been compared to other neuroleptic agents. Against haloperidol, though there was no significant difference in efficacy at the end of the study, clocapramine tended to be superior in alleviating motor retardation, alogia, and thought disorder, and also produced fewer side effects.^[12] Against sulpiride, clocapramine demonstrated more favorable effects in the treatment of both positive and negative symptoms, including motor retardation, delusions, hallucinations, and social isolation, though it produced more side effects.^[13] Against timiperone, clocapramine showed lower efficacy against both positive and negative symptoms and produced more side effects such as dyskinesia, insomnia, constipation, and nausea.^[14]

Clocapramine has been implicated in at least one fatality, a suicide in which there were two self-inflicted stab wounds and an overdose of clocapramine as well as three other antipsychotics was taken.^[15] The stab wounds could not explain the death, and thus, it was attributed to multiple drug toxicity instead.^[15]

See also

• Carpipramine
• Mosapramine
• Penfluridol (typical antipsychotic)