U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ACETOPHENAZINE MALEATE

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

Description
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

Schering
47
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/Acetophenazine.html

Approval Year

1961
146
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 0.8 µM [Ki]
Antagonist
2778
 17.0 nM [IC50]
Antagonist
2778
 36.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

1961
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

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

PubMed

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

Patents

JP4787919B2
9
US2985654
2

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
Name Type Language
ACETOPHENAZINE MALEATE
MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
ACETOPHENAZINE DIMALEATE
MI  
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 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
NCI_THESAURUS C740
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65210
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
SMS_ID
100000078827
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
MESH
C100162
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
NSC
70600
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
FDA UNII
3P5HNU5JTC
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
EVMPD
SUB00255MIG
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
DRUG BANK
DBSALT001415
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID7047851
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
PUBCHEM
5281082
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-202-3
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
CHEBI
2402
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
RXCUI
91127
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY RxNorm
CAS
5714-00-1
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL1085
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY
NSC
169180
Created by admin on Fri Dec 15 16:36:36 GMT 2023 , Edited by admin on Fri Dec 15 16:36:36 GMT 2023
PRIMARY
MERCK INDEX
m991
Created by admin on Fri Dec 15 16:36:35 GMT 2023 , Edited by admin on Fri Dec 15 16:36:35 GMT 2023
PRIMARY Merck Index
ACTIVE MOIETY
Structure of ACETOPHENAZINE
PARENT (SALT/SOLVATE)
Structure of MALEIC ACID
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966