ACETOPHENAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29N3O2S
Molecular Weight	411.56
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN4CCN(CCO)CC4)C2=C1

InChI

InChIKey=WNTYBHLDCKXEOT-UHFFFAOYSA-N

InChI=1S/C23H29N3O2S/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/h2-3,5-8,17,27H,4,9-16H2,1H3

HIDE SMILES / InChI

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 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17606915	Antagonist 2849	0.8 µM [Ki]
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6147851	Antagonist 2849	17.0 nM [IC50]
Sigma opioid receptor 64 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6147851	Antagonist 2849	36.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16 Sources: http://www.psyweb.com/drughtm/jsp/acetop.jsp	Primary		Approved 8583	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 1961

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
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.	2010-03-03	20209133
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.	2007-07-17	17606915
Management of the behavioral and psychological symptoms of dementia.	2007	18225462
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.	1984-09	6147851
Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action.	1978-10	702341
Acetophenazine and diazepam in anxious depressions.	1971-03	5100621
Acetophenazine for office treatment of paranoid symptoms.	1967-03-01	6072166
Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients.	1967-03-01	5336562
EFFECTS OF ACETOPHENAZINE DIMALEATE ON PARANOID SYMPTOMATOLOGY IN FEMALE GERIATRIC PATIENTS: DOUBLE-BLIND STUDY.	1964-09	14212064
[CLINICAL OBSERVATIONS ON THE ACTION OF TINDAL IN PSYCHIATRIC TREATMENT].	1964-07-01	14249556
The treatment of ambulatory adolescent schizophrenia with acetophenazine.	1963-07	14025118
Acetophenazine (Tindal) in the treatment of 80 chronically ill patients with anxiety and tension: double-blind study.	1963-05	14020672
Clinical experiences with acetophenazine in the elderly psychotic.	1963-05	14001420
Acetophenazine for hyperactive geriatric patients.	1962-09	13904111
Acetophenazine in ambulatory schizophrenic adults.	1962-09	13883576
Influence of acetophenazine (Tindal) upon the attitude of cardiac patients.	1962-03	13922058
Acetophenazine (Tindal) and thiopropazate (Dartal) in ambulatory psychoneurotic patients.	1961-10	13883575

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 `Mon Mar 31 17:34:07 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:07 GMT 2025`
Record UNII	8620H6K4QH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETOPHENAZINE [MI]

Preferred Name

English

ACETOPHENAZINE

Official Name

English

Acetophenazine [WHO-DD]

Common Name

English

acetophenazine [INN]

Common Name

English

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

Systematic Name

English

ACETOPHENAZINE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710