MOPERONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H26FNO2
Molecular Weight	355.4457
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)C2(O)CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2

InChI

InChIKey=AGAHNABIDCTLHW-UHFFFAOYSA-N

InChI=1S/C22H26FNO2/c1-17-4-8-19(9-5-17)22(26)12-15-24(16-13-22)14-2-3-21(25)18-6-10-20(23)11-7-18/h4-11,26H,2-3,12-16H2,1H3

HIDE SMILES / InChI

Molecular Formula	C22H26FNO2
Molecular Weight	355.4457
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1838
Curator's Comment: Description was created based on several sources, including http://www.genome.jp/dbget-bin/www_bget?D02623+D01105

Moperone is a first-generation (typical) antipsychotic drug that belongs to the butyrophenone type approved in Japan for the treatment of schizophrenia. It has higher antagonist affinity for D2- than 5-HT2A-receptors. It also has high binding affinity for sigma receptors. It was indicated for schizophrenia, paranoid state, psychoses, epilepsy,alcohol withdrawal syndrome. It can induce extrapyramidal motor side effects, insomnia, and thirst, but it displays generally low toxicity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11561089	Inverse Agonist 80	87.0 nM [EC50]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11561089	Antagonist 2778	1.5 nM [Ki]
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17403993	Inverse Agonist 80	6.1 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5704626	Primary		Approved 8429	Luvatrene Approved Use For the treatment of schizophrenia
Paranoid state 2 Sources: http://www.ndrugs.com/?s=moperone	Primary		Approved 8429	Luvatrene Approved Use Indications: schizophrenia, paranoid state

PubMed

Title	Date	PubMed
Automated on-line in-tube solid-phase microextraction coupled with HPLC/MS/MS for the determination of butyrophenone derivatives in human plasma.	2009 Jun	19387622

Patents

Sample Use Guides

In Vivo Use Guide

Starting dose is 0.2-0.3 mg/kg/day; then slowly increase to 0.04-0.06 mg/kg/day

Route of Administration: Unknown

In Vitro Use Guide

Moperone was tested at a 3 uM concentration

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:25 GMT 2023` Edited by `admin` on `Fri Dec 15 16:20:25 GMT 2023`
Record UNII	OU730881W5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MOPERONE

Official Name

English

R 1658

Code

English

Moperone [WHO-DD]

Common Name

English

moperone [INN]

Common Name

English

MOPERONE HYDROCHLORIDE [JAN]

Common Name

English

4'-FLUORO-4-(4-HYDROXY-4-P-TOLYLPIPERIDINO)BUTYROPHENONE

Common Name

English

MOPERONE [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05AD04