CARPHENAZINE MALEATE

US Previously Marketed

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 Search

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

Description
Sources: http://www.tabletwise.com/us/proketazine-tablet
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

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: https://www.drugbank.ca/drugs/DB01038 \| http://edudrugs.com/P/Proketazine/more.html	Antagonist 2778
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.drugbank.ca/drugs/DB01038 \| http://edudrugs.com/P/Proketazine/more.html	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.tabletwise.com/us/proketazine-tablet https://www.ncbi.nlm.nih.gov/pubmed/13706536 https://www.ncbi.nlm.nih.gov/pubmed/14218188	Primary		Approved 8429	PROKETAZINE Approved Use Used in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

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

PubMed

Title	Date	PubMed
Carphenazine in the intensive care of chronically ill psychotics.	1967 Aug	4863506
Evaluation of carphenazine in hospitalized schizophrenic women.	1967 Feb	6021593
Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial.	1967 Nov	4889058

Patents

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

Name

Type

Language

CARPHENAZINE MALEATE

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

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

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