TIMIPERONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H24FN3OS
Molecular Weight	397.509
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)N3C(=S)NC4=C3C=CC=C4

InChI

InChIKey=YDLQKLWVKKFPII-UHFFFAOYSA-N

InChI=1S/C22H24FN3OS/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)

HIDE SMILES / InChI

Molecular Formula	C22H24FN3OS
Molecular Weight	397.509
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10215017
Curator's Comment: description was created based on several sources, including: https://medical.mt-pharma.co.jp/di/file/dc/tol_f.htm https://www.medicallibrary-dsc.info/di/tolopelon_tablets_3mg/pdf/if_tp_tab_1301_09.pdf

Timiperone is a neuroleptic agent that was developed in Japan. Timiperone has a potent antipsychotic activity, which is comparable to other butyrophenones such as haloperidol (HAL). Timiperone has a five-eight-times higher affinity to dopamine receptors and a 15-times higher affinity to serotonin receptors than those of HAL. Clinical trials have suggested that TIM has a specific action against negative symptoms such as lack of initiative or blunted affect as well as positive symptoms such as delusions and hallucinations in schizophrenics.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: http://www.ncbi.nlm.nih.gov/pubmed/43256 \| http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1902 \| http://www.genome.jp/dbget-bin/www_bget?D02035	Antagonist 2849
serotonin receptor signaling pathway 6 Target ID: GO:0007210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/43256 \| http://www.ncbi.nlm.nih.gov/pubmed/10215017	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00048858	Primary		Approved 8583	Tolopelon Approved Use Timiperone is efficient against schizophrenia. Launch Date 1983

C_max

Value	Dose	Co-administered	Analyte	Population
5.947 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/6/530258_1179026C1040_6_003_1F.pdf#page=22	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
13.6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530258_1179405A1032_4_004_1F.pdf#page=19	4 mg single, intramuscular dose: 4 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
39.321 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/6/530258_1179026C1040_6_003_1F.pdf#page=22	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
175.3 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530258_1179405A1032_4_004_1F.pdf#page=19	4 mg single, intramuscular dose: 4 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.906 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/6/530258_1179026C1040_6_003_1F.pdf#page=22	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
15.7 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530258_1179405A1032_4_004_1F.pdf#page=19	4 mg single, intramuscular dose: 4 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		TIMIPERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/6/530258_1179026C1040_6_003_1F.pdf#page=24 \| https://www.jstage.jst.go.jp/article/cpb1958/31/4/31_4_1411/_article/-char/en			TIMIPERONE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
18 mg 1 times / day steady-state, oral Studied dose Dose: 18 mg, 1 times / day Route: oral Route: steady-state Dose: 18 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10215017/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10215017/	Sources: https://pubmed.ncbi.nlm.nih.gov/10215017/

PubMed

Title	Date	PubMed
Atypical properties of several classes of antipsychotic drugs on the basis of differential induction of Fos-like immunoreactivity in the rat brain.	2004-11-26	15519367
Effect of hyperprolactinemia induced by pituitary grafts or castration on porphyrin content of the mouse Harderian gland.	2001-08	11552298

Patents

Sample Use Guides

In Vivo Use Guide

Dosage gradually increase from 0,5-3 mg to 3-12 mg daily during 12 weeks

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:13 GMT 2025`
Record UNII	626DQ7N19L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIMIPERONE

Official Name

English

TOLOPELON

Preferred Name

English

timiperone [INN]

Common Name

English

TIMIPERONE [MI]

Common Name

English

TIMIPERONE [MART.]

Common Name

English

TIMIPERONE [JAN]

Common Name

English

DD-3480

Code

English

4-FLUORO-4-(4-(2-THIOXO-1-BENZIMIDAZOLINYL)PIPERIDINO)BUTYROPHENONE

Systematic Name

English

Timiperone [WHO-DD]

Common Name

English

1-BUTANONE, 4-(4-(2,3-DIHYDRO-2-THIOXO-1H-BENZIMIDAZOL-1-YL)-1-PIPERIDINYL)-1-(4-FLUOROPHENYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197