PEROSPIRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H30N4O2S
Molecular Weight	426.575
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1[C@H]2CCCC[C@H]2C(=O)N1CCCCN3CCN(CC3)C4=NSC5=C4C=CC=C5

InChI

InChIKey=FBVFZWUMDDXLLG-HDICACEKSA-N

InChI=1S/C23H30N4O2S/c28-22-17-7-1-2-8-18(17)23(29)27(22)12-6-5-11-25-13-15-26(16-14-25)21-19-9-3-4-10-20(19)30-24-21/h3-4,9-10,17-18H,1-2,5-8,11-16H2/t17-,18+

HIDE SMILES / InChI

Molecular Formula	C23H30N4O2S
Molecular Weight	426.575
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB08922
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12054062

Perospirone (Lullan®) is an atypical antipsychotic of the azapirone family. It is used in Japan for the treatment of schizophrenia and acute cases of bipolar mania. Its primary mode of action is through antagonism of serotonin 5-HT2A and dopamine D2 receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12054062	Antagonist 2849	0.6 nM [Kd]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9577836	Antagonist 2849	0.09 nM [Kd]
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12054062	Antagonist 2849	1.3 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.drugbank.ca/drugs/DB08922	Palliative		Approved 8583	LULLAN Approved Use For the treatment of schizophrenia and acute cases of bipolar mania. Launch Date 2000
Bipolar mania 3 Sources: https://www.drugbank.ca/drugs/DB08922	Palliative		Approved 8583	LULLAN Approved Use For the treatment of schizophrenia and acute cases of bipolar mania. Launch Date 2000

C_max

Value	Dose	Analyte	Population
1.9 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
5.7 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.1 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1.7 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.546 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.882 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
7.9 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
13.3 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6.7 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6.9 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.781 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.75 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
13.6 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.93 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.704 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.685 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
26.5 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
51.3 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
18.6 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
20.4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=204 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=20	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
9.637 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15.16 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=209 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=21	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	2-[4-[4-(1,2-BENZOTHIAZOL-3-YL)PIPERAZIN-1-YL]BUTYL]-7A-HYDROXY-4,5,6,7-TETRAHYDRO-3AH-ISOINDOLE-1,3-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=203 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=19	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		PEROSPIRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2.7% OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g001211/82ctdp_1-336.pdf#page=175 \| https://www.info.pmda.go.jp/go/interview/2/400093_1179043F1032_2_022_1F.pdf#page=23			PEROSPIRONE serum	Homo sapiens

Doses

Dose	Population	Adverse events
96 mg 3 times / day multiple, oral Highest studied dose Dose: 96 mg, 3 times / day Route: oral Route: multiple Dose: 96 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11463136/ https://www.cambridge.org/core/books/abs/prescribers-guide/perospirone/12B803C262A3919C1F030E1B16387426# https://adisinsight.springer.com/drugs/800000573	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11463136/ https://www.cambridge.org/core/books/abs/prescribers-guide/perospirone/12B803C262A3919C1F030E1B16387426# https://adisinsight.springer.com/drugs/800000573	Sources: https://pubmed.ncbi.nlm.nih.gov/11463136/ https://www.cambridge.org/core/books/abs/prescribers-guide/perospirone/12B803C262A3919C1F030E1B16387426# https://adisinsight.springer.com/drugs/800000573
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16313704/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16313704/	Disc. AE: Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Neuroleptic malignant syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/16313704/

AEs

AE	Significance	Dose	Population
Neuroleptic malignant syndrome	Disc. AE	8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16313704/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16313704/

PubMed

Title	Date	PubMed
Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors.	1998-03	9577836
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.	1992-04-10	1354163
Brain receptors for antipsychotic drugs and dopamine: direct binding assays.	1975-11	1060115

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 4 mg three times daily taken after meals, and daily dose should not exceed 48 mg.

Route of Administration: Oral

In Vitro Use Guide

The binding affinity of perospirone (SM-9018) for various neurotransmitter and drug-receptors was investigated in the rat brain. SM-9018 possessed very high affinity for 5-HT2, D2 and 5-HT1A receptors (Ki = 0.61, 1.4 and 2.9 nM, respectively), and it had moderate affinity for alpha 1 and D1 receptors (Ki = 17 and 41 nM, respectively). However, SM-9018 had only negligible affinity for alpha 2, opiate, glutamate, phencyclidine, benzodiazepine and GABA-A receptors.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:05:16 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:16 GMT 2025`
Record UNII	N303OK87DT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PEROSPIRONE

Official Name

English

1H-ISOINDOLE-1,3(2H)-DIONE, 2-(4-(4-(1,2-BENZISOTHIAZOL-3-YL)-1-PIPERAZINYL)BUTYL)HEXAHYDRO-, (3AR,7AS)-REL-

Preferred Name

English

perospirone [INN]

Common Name

English

Perospirone [WHO-DD]

Common Name

English

PEROSPIRONE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197