BUTAPERAZINE MALEATE

First approved in 1967

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H31N3OS.2C4H4O4
Molecular Weight	641.732
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CCCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(C)CC4)C=C1

InChI

InChIKey=WVYWSPZQGQMPKW-SPIKMXEPSA-N

InChI=1S/C24H31N3OS.2C4H4O4/c1-3-7-22(28)19-10-11-24-21(18-19)27(20-8-4-5-9-23(20)29-24)13-6-12-26-16-14-25(2)15-17-26;2*5-3(6)1-2-4(7)8/h4-5,8-11,18H,3,6-7,12-17H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula	C24H31N3OS
Molecular Weight	409.587
Charge	0
Count

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4386884 | https://www.ncbi.nlm.nih.gov/pubmed/6111766

Butaperazine is an antipsychotic phenothiazine. As shown in animal studies butaperazine increases striatal and mesolimbic dopamine turnover. Butaperazine is effective in the management of schizophrenia. Extrapyramidal symptoms and drowsiness are the most common adverse effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase 32 Target ID: CHEMBL2095205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6126230	Inhibitor 8297
Dopamine receptor 60 Target ID: CHEMBL2096905 Sources: https://books.google.ru/books?id=fFi7DR2hmaIC&pg=PA979&lpg=PA979&dq=butaperazine retrieved from Kaplan and Sadock's Synopsis of Psychiatry: Behavioral Sciences/Clinical Psychiatry Sadock B. J., Sadock V. A., p.977	Antagonist 2778

C_max

Value	Dose	Co-administered	Analyte	Population
211 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2860932/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTAPERAZINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1990 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2860932/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTAPERAZINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2860932/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTAPERAZINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/(SICI)1099-1077(199807)13:5%3C329::AID-HUP4%3E3.0.CO;2-T	yes		yes (co-administration study) Comment: Coadministration of Desipramine (CYP2D6 substrate) increased Butaperazine concentration. Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/(SICI)1099-1077(199807)13:5%3C329::AID-HUP4%3E3.0.CO;2-T

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY565660	https://www.001chemical.com/chem/653-03-2
ABI Chem	AC1L1ZXR
ABI Chem	AC1Q5GH2
BOC Sciences	653-03-2
Chemieliva Pharmaceutical Co., Ltd	PBCM1373136
Clearsynth	CS-T-09143	https://www.clearsynth.com/en/CST09143.html
Compound Cloud	12598
Compound Cloud	6433234
Molcore	MC565660	https://www.molcore.com/product/653-03-2
MuseChem	M071411
MuseChem	M128772
NovoSeek	12598
Smolecule	S522317	http://www.smolecule.com/products/s522317
THE BioTek	bt-262164	https://www.thebiotek.com/product/inhibitors/bt-262164
ZINC	ZINC000022446639	http://zinc15.docking.org/substances/ZINC000022446639
eMolecules	49259617

PubMed

Title	Date	PubMed

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:46 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:46 GMT 2023`
Record UNII	22VUW43J2H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTAPERAZINE MALEATE

Official Name

English

BUTAPERAZINE DIMALEATE

Common Name

English

BUTAPERAZINE MALEATE [USAN]

Common Name

English

1-BUTANONE, 1-(10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (Z)-2-BUTENEDIOATE (1:2)

Systematic Name

English

BUTAPERAZINE DIMALEATE [MI]

Common Name

English

BUTAPERAZINE MALEATE [MART.]

Common Name

English

Butaperazine maleate [WHO-DD]

Common Name

English

1-[10-[3-(4-Methyl-1-piperazinyl)propyl]phenothiazin-2-yl]-1-butanone maleate (1:2)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884