PROPIOMAZINE MALEATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H24N2OS.C4H4O4
Molecular Weight	456.555
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CC(C)N(C)C)C2=C1

InChI

InChIKey=ILEKKZUHFYUQIE-BTJKTKAUSA-N

InChI=1S/C20H24N2OS.C4H4O4/c1-5-18(23)15-10-11-20-17(12-15)22(13-14(2)21(3)4)16-8-6-7-9-19(16)24-20;5-3(6)1-2-4(7)8/h6-12,14H,5,13H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;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	C20H24N2OS
Molecular Weight	340.482
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14035428 | http://www.druginfosys.com/drug.aspx?drugcode=2049&type=1

Propiomazine is a typical antipsychotic, blocking H1 receptors and is primarily indicated in conditions Insomnia. Propiomazine was also used under brand name largon for the relief of restlessness and apprehension, preoperatively or during surgery. In addition largon was used as an adjunct to analgesics for the relief of restlessness and apprehension during labor. But this drug was discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Restlessness 6 Sources: https://www.drugs.com/mmx/largon.html	Palliative	Approved 8429	LARGON Approved Use Unknown Launch Date 1960
Apprehension 3 Sources: https://www.drugs.com/mmx/largon.html	Palliative	Approved 8429	LARGON Approved Use Unknown Launch Date 1960
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14035428	Primary	Phase IV 63	Unknown Approved Use Unknown

T_1/2

Value	Dose	Analyte	Population
7.7 h EXPERIMENT https://www.scopus.com/record/display.uri?eid=2-s2.0-0019424663&origin=inward&txGid=47771f176f85945174ddee4f8734fce1	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PROPIOMAZINE serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
10.8 h EXPERIMENT https://www.scopus.com/record/display.uri?eid=2-s2.0-0019424663&origin=inward&txGid=47771f176f85945174ddee4f8734fce1	single, intramuscular	PROPIOMAZINE serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
8.6 h EXPERIMENT https://www.scopus.com/record/display.uri?eid=2-s2.0-0019424663&origin=inward&txGid=47771f176f85945174ddee4f8734fce1	single, oral	PROPIOMAZINE serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
19% OTHER https://go.drugbank.com/drugs/DB00777			PROPIOMAZINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0379073898001698	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8491	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8491
ChemicalBook	CB7934557	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7934557
eMolecules	35867570	https://www.emolecules.com/cgi-bin/more?vid=35867570

PubMed

Title	Date	PubMed
Interaction of protonated anticancer thiazines with water-insoluble phospholipids and antineoplastic agents.	2002 Mar-Apr	12014679
Mucosal delivery of cytotoxic therapeutic agents: response of rat nasal mucosa to microencapsulated ethopropazine HCl enantiomer.	2005 Nov	16421084
Are sedatives and hypnotics associated with increased suicide risk of suicide in the elderly?	2009 Jun 4	19497093
Socioeconomic determinants of psychotropic drug utilisation among elderly: a national population-based cross-sectional study.	2010 Mar 9	20214796

Patents

Sample Use Guides

In Vivo Use Guide

Usual adult dose: Preoperative: intramuscular or intravenous: 20 to 40 mg administered in conjunction with 50 mg of meperidine. Sedation during surgery with local, nerve block, or spinal anesthesia: intramuscular or intravenous 10 to 20 mg. Analgesia adjunct, during labor: intramuscular or intravenous, 20 to 40 mg in the early stages of labor, then 20 to 40 mg of propiomazine administered in conjunction with 25 to 75 mg of meperidine when labor is definitely established. Doses may be repeated every three hours, if necessary. Usual pediatric dose: sedation prior to surgery: preanesthetic or postoperative: children up to 27 kg: Intramuscular or intravenous, 550 mcg (0.55 mg) to 1.1 mg per kg of body; children 2 to 4 years of age: Intramuscular or intravenous, 10 mg; children 4 to 6 years of age: Intramuscular or intravenous, 15 mg; children 6 to 12 years of age: Intramuscular or intravenous, 25 mg. insomnia: 25 to 50 mg oral

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:41:35 GMT 2023` Edited by `admin` on `Sat Dec 16 04:41:35 GMT 2023`
Record UNII	OEY0ZC43SA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPIOMAZINE MALEATE

Common Name

English

PROPIOMAZINE MONOMALEATE

Common Name

English

1-PROPANONE, 1-(10-(2-(DIMETHYLAMINO)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (2Z)-2-BUTENEDIOATE (1:1)

Systematic Name

English

Propiomazine maleate [WHO-DD]

Common Name

English

DOREVANE

Brand Name

English

INDORM

Brand Name

English

1-PROPANONE, 1-(10-(2-(DIMETHYLAMINO)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (±)-, (2Z)-2-BUTENEDIOATE (1:1)

Common Name

English

Code System Code Type Description

CAS

3568-23-8