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Details

Stereochemistry ACHIRAL
Molecular Formula C24H31N3O2S.2C4H4O4
Molecular Weight 657.731
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CARPHENAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(CCO)CC4)C=C1

InChI

InChIKey=TVPJGGZLZLUPOB-SPIKMXEPSA-N
InChI=1S/C24H31N3O2S.2C4H4O4/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28;2*5-3(6)1-2-4(7)8/h3-4,6-9,18,28H,2,5,10-17H2,1H3;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 C24H31N3O2S
Molecular Weight 425.587
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://edudrugs.com/P/Proketazine/more.html | https://en.wikipedia.org/wiki/Carfenazine | https://www.ncbi.nlm.nih.gov/pubmed/14267601

Carfenazine (brand name Proketazine) is an antipsychotic and tranquilizer of the phenothiazine group. It is used in the treatment of acute or chronic schizophrenic reactions in hospitalized patients. Proketazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis. The following is a list of possible side effects that may occur from all constituting ingredients of Proketazine: akathisia, tardive dyskinesia, extrapyramidal symptoms, allergic purpura.

CNS Activity

Originator

Approval Year

1963
70
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
PROKETAZINE

Approved Use

Used in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.
Doses

Doses

DosePopulationAdverse events​
100 mg 4 times / day steady, oral
Dose: 100 mg, 4 times / day
Route: oral
Route: steady
Dose: 100 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
unhealthy, 18 - 60 years
n = 28
Health Status: unhealthy
Condition: acutely psychotic
Age Group: 18 - 60 years
Sex: F
Population Size: 28
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
Disc. AE: Skin rash...
Other AEs: Faintness...
AEs leading to
discontinuation/dose reduction:
Skin rash (grade 4, 1 patient)
Other AEs:
Faintness (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
AEs

AEs

AESignificanceDosePopulation
Faintness 1 patient
100 mg 4 times / day steady, oral
Dose: 100 mg, 4 times / day
Route: oral
Route: steady
Dose: 100 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
unhealthy, 18 - 60 years
n = 28
Health Status: unhealthy
Condition: acutely psychotic
Age Group: 18 - 60 years
Sex: F
Population Size: 28
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
Skin rash grade 4, 1 patient
Disc. AE
100 mg 4 times / day steady, oral
Dose: 100 mg, 4 times / day
Route: oral
Route: steady
Dose: 100 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
unhealthy, 18 - 60 years
n = 28
Health Status: unhealthy
Condition: acutely psychotic
Age Group: 18 - 60 years
Sex: F
Population Size: 28
Sources:
https://pubmed.ncbi.nlm.nih.gov/14286057/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:51235
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51235
ZINC
ZINC000064624931
http://zinc15.docking.org/substances/ZINC000064624931
PubMed

PubMed

TitleDatePubMed
Carphenazine in the intensive care of chronically ill psychotics.
1967 Aug
Evaluation of carphenazine in hospitalized schizophrenic women.
1967 Feb
Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial.
1967 Nov
Patents

Patents

US 3023146
2
US2985654 A
2

Sample Use Guides

In Vivo Use Guide
First week, 25 mg. t.i.d.; second week, 50 mg. t.i.d.; third week, 75 mg. t.i.d.; fourth week, 100 mg. t.i.d.; fifth week and thereafter, 100 mg. q.i.d.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:25:22 UTC 2023
Edited
by admin
on Fri Dec 15 16:25:22 UTC 2023
Record UNII
0HX1Z0A2MC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARPHENAZINE MALEATE
ORANGE BOOK   USAN  
USAN  
Official Name English
1-(10-(3-(4-(2-HYDROXYETHYL)PIPERAZIN-1-YL)PROPYL)-10H-PHENOTHIAZIN-2-YL)PROPAN-1-ONE DI((2Z)-BUT-2-ENEDIOATE) (SALT)
Common Name English
CARFENAZINE MALEATE [MART.]
Common Name English
PROKETAZINE
Brand Name English
CARPHENAZINE MALEATE [USAN]
Common Name English
CARPHENAZINE DIMALEATE [MI]
Common Name English
NSC-71755
Code English
CARFENAZINE MALEATE
MART.   WHO-DD  
Common Name English
1-PROPANONE, 1-(10-(3-(4-(2-HYDROXYETHYL)-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (2Z)-2-BUTENEDIOATE (1:2) (SALT)
Common Name English
1-[10-[3-[4-(2-Hydroxyethyl)-1-piperazinyl]propyl]phenothiazin-2-yl]-1-propanone maleate (1:2)
Systematic Name English
WY-2445
Code English
CARPHENAZINE DIMALEATE
MI  
Common Name English
Carfenazine maleate [WHO-DD]
Common Name English
CARPHENAZINE MALEATE [ORANGE BOOK]
Common Name English
1-PROPANONE, 1-(10-(3-(4-(2-HYDROXYETHYL)-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C740
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID2047852
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
NSC
71755
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
NCI_THESAURUS
C65289
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
FDA UNII
0HX1Z0A2MC
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
DRUG BANK
DBSALT001419
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
CHEBI
51241
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
CAS
2975-34-0
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
EVMPD
SUB01059MIG
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
SMS_ID
100000084893
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
PUBCHEM
6433356
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201328
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
221-019-2
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY
MERCK INDEX
m1057
Created by admin on Fri Dec 15 16:25:22 UTC 2023 , Edited by admin on Fri Dec 15 16:25:22 UTC 2023
PRIMARY Merck Index
Related Record Type Details
Structure of MALEIC ACID
PARENT -> SALT/SOLVATE
Structure of CARPHENAZINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CARPHENAZINE
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