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=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(CCO)CC4)C=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 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
Acetophenazine (Tindal) and thiopropazate (Dartal) in ambulatory psychoneurotic patients.	1961 Oct	13883575
Influence of acetophenazine (Tindal) upon the attitude of cardiac patients.	1962 Mar	13922058
The treatment of ambulatory adolescent schizophrenia with acetophenazine.	1963 Jul	14025118
Acetophenazine (Tindal) in the treatment of 80 chronically ill patients with anxiety and tension: double-blind study.	1963 May	14020672
Clinical experiences with acetophenazine in the elderly psychotic.	1963 May	14001420
[CLINICAL OBSERVATIONS ON THE ACTION OF TINDAL IN PSYCHIATRIC TREATMENT].	1964 Jul-Aug	14249556
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
Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients.	1967 Mar-Apr	5336562
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
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.	2010 Mar 3	20209133

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 14:59:16 UTC 2023` Edited by `admin` on `Fri Dec 15 14:59:16 UTC 2023`
Record UNII	8620H6K4QH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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 [MI]

Common Name

English

ACETOPHENAZINE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710