ACETOPHENAZINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29N3O2S.2C4H4O4
Molecular Weight	643.705
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.CC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(CCO)CC4)C=C1

InChI

InChIKey=NUKVZKPNSKJGBK-SPIKMXEPSA-N

InChI=1S/C23H29N3O2S.2C4H4O4/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27;2*5-3(6)1-2-4(7)8/h2-3,5-8,17,27H,4,9-16H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

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

Molecular Formula	C23H29N3O2S
Molecular Weight	411.56
Charge	0
Count

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

Description
Sources: http://www.psyweb.com/drughtm/jsp/acetop.jsp
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17606915 | https://www.ncbi.nlm.nih.gov/pubmed/6147851

Acetophenazine (Tindal) is an antipsychotic drug of moderate-potency. Used in the treatment of disorganized and psychotic thinking. Acetophenazine (Tindal) is also used to help treat false perceptions (e.g. hallucinations or delusions). Acetophenazine acts as an antagonist of dopaminergic D2 receptors in the brain. Acetophenazine exhibited modest androgen receptor binding and antiandrogen activity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17606915	Antagonist 2778	0.8 µM [Ki]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6147851	Antagonist 2778	17.0 nM [IC50]
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6147851	Antagonist 2778	36.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16 Sources: http://www.psyweb.com/drughtm/jsp/acetop.jsp	Primary		Approved 8429	TINDAL Approved Use Acetophenazine ( Tindal ) is an antipsychotic drug of moderate-potency. Used in the treatment of disorganized and psychotic thinking. Acetophenazine ( Tindal ) is also used to help treat false perceptions (e.g. hallucinations or delusions.) Launch Date -2.75875201E11

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% REVIEW https://jamanetwork.com/journals/jama/article-abstract/182936	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		ACETOPHENAZINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2401	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2401
ZINC	ZINC000022446634	http://zinc15.docking.org/substances/ZINC000022446634

PubMed

Title	Date	PubMed
Clinical experiences with acetophenazine in the elderly psychotic.	1963 May	14001420
EFFECTS OF ACETOPHENAZINE DIMALEATE ON PARANOID SYMPTOMATOLOGY IN FEMALE GERIATRIC PATIENTS: DOUBLE-BLIND STUDY.	1964 Sep	14212064
Acetophenazine for office treatment of paranoid symptoms.	1967 Mar-Apr	6072166
Acetophenazine and diazepam in anxious depressions.	1971 Mar	5100621
Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action.	1978 Oct	702341
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.	1984 Sep	6147851
Management of the behavioral and psychological symptoms of dementia.	2007	18225462
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.	2007 Jul 17	17606915

Patents

Sample Use Guides

In Vivo Use Guide

Normal dosage: 20mg to 40mg daily, in healthy young adult. Start: 20mg daily. Increases: 20mg as needed. Maintenance: As low as possible in 24 hours. Maximum: 60mg in 24 hours.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:36:35 UTC 2023` Edited by `admin` on `Fri Dec 15 16:36:35 UTC 2023`
Record UNII	3P5HNU5JTC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ACETOPHENAZINE MALEATE

Official Name

English

ACETOPHENAZINE DIMALEATE

Common Name

English

ETHANONE, 1-(10-(3-(4-(2-HYDROXYETHYL)-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (Z) 2-BUTENEDIOATE (1:2) (SALT)

Common Name

English

ACETOPHENAZINE DIMALEATE [MI]

Common Name

English

ACETOPHENAZINE MALEATE [ORANGE BOOK]

Common Name

English

NSC-70600

Code

English

ACEPHENAZINE DIMALEATE

Common Name

English

ACETOPHENAZINE MALEATE [USAN]

Common Name

English

ACETOPHENAZINE MALEATE [VANDF]

Common Name

English

10-[3-[4-(2-Hydroxyethyl)-1-piperazinyl]propyl]phenothiazin-2-yl methyl ketone maleate (1:2) (salt)

Common Name

English

Acetophenazine maleate [WHO-DD]

Common Name

English

ACETOPHENAZINE MALEATE [MART.]

Common Name

English

TINDAL

Brand Name

English

SCH 6673

Code

English

NSC-169180

Code

English

SCH-6673

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29710

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

NCI_THESAURUS

C740

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

Code System Code Type Description

NCI_THESAURUS

C65210

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

PRIMARY

SMS_ID

100000078827

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

PRIMARY

MESH

C100162

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

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NSC

70600

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

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FDA UNII

3P5HNU5JTC

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

EVMPD

SUB00255MIG

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

DRUG BANK

DBSALT001415

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

EPA CompTox

DTXSID7047851

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

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PUBCHEM

5281082

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

PRIMARY

ECHA (EC/EINECS)

227-202-3

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

CHEBI

2402

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

RXCUI

91127

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

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RxNorm

CAS

5714-00-1

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

ChEMBL

CHEMBL1085

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

NSC

169180

Created by admin on Fri Dec 15 16:36:36 UTC 2023 , Edited by admin on Fri Dec 15 16:36:36 UTC 2023

PRIMARY

MERCK INDEX

m991

Created by admin on Fri Dec 15 16:36:35 UTC 2023 , Edited by admin on Fri Dec 15 16:36:35 UTC 2023

PRIMARY

Merck Index

Related Record Type Details


					8620H6K4QH

ACETOPHENAZINE

PARENT -> SALT/SOLVATE


					91XW058U2C

MALEIC ACID

PARENT -> SALT/SOLVATE

Related Record Type Details


					8620H6K4QH

ACETOPHENAZINE

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: http://www.psyweb.com/drughtm/jsp/acetop.jspCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17606915 | https://www.ncbi.nlm.nih.gov/pubmed/6147851

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Funbound

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.psyweb.com/drughtm/jsp/acetop.jsp
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17606915 | https://www.ncbi.nlm.nih.gov/pubmed/6147851

F_unbound