PEROSPIRONE HYDROCHLORIDE DIHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H30N4O2S.ClH.2H2O
Molecular Weight	499.066
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PEROSPIRONE HYDROCHLORIDE DIHYDRATE

Structure Search

SMILES

O.O.Cl.[H][C@@]12CCCC[C@]1([H])C(=O)N(CCCCN3CCN(CC3)C4=NSC5=C4C=CC=C5)C2=O

InChI

InChIKey=LZQKLGXZZSMREH-SMMZMSQNSA-N

InChI=1S/C23H30N4O2S.ClH.2H2O/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;1H;2*1H2/t17-,18+;;;

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12054062	Antagonist 2778	0.6 nM [Kd]
Dopamine D4 receptor 71 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9577836	Antagonist 2778	0.09 nM [Kd]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12054062	Antagonist 2778	1.3 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.drugbank.ca/drugs/DB08922	Palliative		Approved 8429	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 8429	LULLAN Approved Use For the treatment of schizophrenia and acute cases of bipolar mania. Launch Date 2000

PubMed

Title	Date	PubMed
Brain receptors for antipsychotic drugs and dopamine: direct binding assays.	1975 Nov	1060115
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.	1992 Apr 10	1354163
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 Mar	9577836

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 `Fri Dec 15 19:12:49 GMT 2023` Edited by `admin` on `Fri Dec 15 19:12:49 GMT 2023`
Record UNII	S03S4466IP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PEROSPIRONE HYDROCHLORIDE DIHYDRATE

Common Name

English

CIS-N-(4-(4-(1,2-BENZISOTHIAZOL-3-YL)-1-PIPERAZINYL)BUTYL)-1,2-CYCLOHEXANEDICARBOXIMIDE HYDROCHLORIDE DIHYDRATE

Common Name

English

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

Common Name

English

Perospirone hydrochloride dihydrate [WHO-DD]

Common Name

English

PEROSPIRONE HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

PEROSPIRONE HYDROCHLORIDE HYDRATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID70172763