ACETOPHENAZINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29N3O2S.2C4H4O4
Molecular Weight	643.705
Optical Activity	UNSPECIFIED
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=CC=C2SC3=C(C=CC=C3)N(CCCN4CCN(CCO)CC4)C2=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	C23H29N3O2S
Molecular Weight	411.56
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry
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
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

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	Condition	Potency
Sigma opioid receptor 55	Antagonist 2438		36.0 nM [Ki]
Androgen Receptor 153	Antagonist 2438		0.8 µM [Ki]
Dopamine D2 receptor 270	Antagonist 2438	Psychoses	17.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychoses 7	Primary	Dopamine D2 receptor	Approved 7777	TINDAL

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
Acetophenazine for hyperactive geriatric patients.	1962 Sep	13904111
Acetophenazine in ambulatory schizophrenic adults.	1962 Sep	13883576
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
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

Substance Class	Chemical Created by `admin` on `Tue Oct 22 06:07:00 UTC 2019` Edited by `admin` on `Tue Oct 22 06:07:00 UTC 2019`
Record UNII	3P5HNU5JTC
Record Status	`Validated (UNII)`
Record Version

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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 [MART.]

Common Name

English

TINDAL

Brand Name

English

ACETOPHENAZINE MALEATE [WHO-DD]

Common Name

English

SCH 6673

Code

English

NSC-169180

Code

English

SCH-6673

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29710