PROFENAMINE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H24N2S
Molecular Weight	312.472
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)C(C)CN1C2=CC=CC=C2SC3=C1C=CC=C3

InChI

InChIKey=CDOZDBSBBXSXLB-UHFFFAOYSA-N

InChI=1S/C19H24N2S/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21/h6-13,15H,4-5,14H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/mmx/parsitan.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21740955 | https://www.ncbi.nlm.nih.gov/pubmed/2904117

Ethopropazine is an anticholinergic drug. Ethopropazine is an inhibitor of butyrylcholinesterase and non-selective muscarinic acetylcholine receptor antagonist. Ethopropazine has been used for the treatment of parkinsonism and drug-induced extrapyramidal reactions. Also It used for the symptomatic treatment of hepatolenticular degeneration and congenital athetosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Butyrylcholinesterase 46 Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21740955	Inhibitor 8297		88.0 nM [Kd]
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20732256 \| https://www.ncbi.nlm.nih.gov/pubmed/2236897 \| https://www.ncbi.nlm.nih.gov/pubmed/2904117	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.drugs.com/mmx/parsitan.html	Primary	Approved 8429	PARSIDOL Approved Use Ethopropazine is indicated for the treatment of parkinsonism and drug-induced extrapyramidal reactions. Also used for the symptomatic treatment of hepatolenticular degeneration and congenital athetosis.
Congenital athetosis 3 Sources: https://www.drugs.com/mmx/parsitan.html	Primary	Approved 8429	PARSIDOL Approved Use Ethopropazine is indicated for the treatment of parkinsonism and drug-induced extrapyramidal reactions. Also used for the symptomatic treatment of hepatolenticular degeneration and congenital athetosis.
Drug-induced extrapyramidal reactions 3 Sources: https://www.drugs.com/mmx/parsitan.html	Primary	Approved 8429	PARSIDOL Approved Use Ethopropazine is indicated for the treatment of parkinsonism and drug-induced extrapyramidal reactions. Also used for the symptomatic treatment of hepatolenticular degeneration and congenital athetosis.
Hepatolenticular degeneration 3 Sources: https://www.drugs.com/mmx/parsitan.html	Primary	Approved 8429	PARSIDOL Approved Use Ethopropazine is indicated for the treatment of parkinsonism and drug-induced extrapyramidal reactions. Also used for the symptomatic treatment of hepatolenticular degeneration and congenital athetosis.

F_unbound

Value	Dose	Co-administered	Analyte	Population
7% OTHER https://go.drugbank.com/drugs/DB00392			PROFENAMINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3720659/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:313639	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:313639
eMolecules	1986772	https://www.emolecules.com/cgi-bin/more?vid=1986772

PubMed

Title	Date	PubMed
Abnormal involuntary movements induced by anticholinergic therapy.	1974	4155220
Amantadine in drug-induced extrapyramidal signs: a comparative study.	1975 Jun	239908
Ethopropazine and benztropine in neuroleptic-induced parkinsonism.	1979 Mar	33969
The relative selectivity of anticholinergic drugs for the M1 and M2 muscarinic receptor subtypes.	1986	2904117
Anti-nicotinic properties of anticholinergic antiparkinson drugs.	1998 Nov	9877318
Butyrylcholinesterase and cognitive function.	2001 Dec	12003252
Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase.	2008 Oct 15	18656440
Recombinant expression and biochemical characterization of the catalytic domain of acetylcholinesterase-1 from the African malaria mosquito, Anopheles gambiae.	2009 Sep	19607916

Patents

Sample Use Guides

In Vivo Use Guide

ETHOPROPAZINE HYDROCHLORIDE TABLETS USP Usual adult and adolescent dose Parkinsonism and Drug-induced extrapyramidal reactions Oral, 50 mg one or two times a day, the dosage being increased as needed and tolerated. In severe cases, the dose may be increased gradually to a total of 500 to 600 mg a day.

Route of Administration: Oral

In Vitro Use Guide

The racemate and the enantiomers of ethopropazine were tested in vitro for their cellular toxicity using lung fibroblast cells. Each enantiomer was shown to be cytotoxic at concentrations greater than 10 uM.

Name

Type

Language

PROFENAMINE

Official Name

English

W-483

Code

English

10H-PHENOTHIAZINE-10-ETHANAMINE, N,N-DIETHYL-.ALPHA.-METHYL-

Systematic Name

English

ETHOPROPAZINE [MI]

Common Name

English

ETHOPROPAZINE

Common Name

English

PHENOTHIAZINE, 10-(2-(DIETHYLAMINO)PROPYL)-

Systematic Name

English

(±)-PROFENAMINE

Common Name

English

(±)-ETHOPROPAZINE

Common Name

English

ETHOPROPAZINE [VANDF]

Common Name

English

Profenamine [WHO-DD]

Common Name

English

profenamine [INN]

Common Name

English

10-(2-(DIETHYLAMINO)PROPYL)PHENOTHIAZINE

Systematic Name

English

RP-3356

Code

English

SC-2538

Code

English

N,N-DIETHYL-.ALPHA.-METHYL-10H-PHENOTHIAZINE-10-ETHANAMINE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QN04AA05