PROPIOMAZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H24N2OS
Molecular Weight	340.482
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)C1=CC=C2SC3=CC=CC=C3N(CC(C)N(C)C)C2=C1

InChI

InChIKey=UVOIBTBFPOZKGP-UHFFFAOYSA-N

InChI=1S/C20H24N2OS/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/h6-12,14H,5,13H2,1-4H3

HIDE SMILES / InChI

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 316 Target ID: CHEMBL231	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Restlessness 6 Sources: https://www.drugs.com/mmx/largon.html	Palliative	Approved 8583	LARGON Approved Use Unknown Launch Date 1960
Apprehension 3 Sources: https://www.drugs.com/mmx/largon.html	Palliative	Approved 8583	LARGON Approved Use Unknown Launch Date 1960
Insomnia 111 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14035428	Primary	Phase IV 63	Unknown Approved Use Unknown

T_1/2

Value	Dose	Analyte	Population
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
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

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 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 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
Socioeconomic determinants of psychotropic drug utilisation among elderly: a national population-based cross-sectional study.	2010-03-09	20214796
Are sedatives and hypnotics associated with increased suicide risk of suicide in the elderly?	2009-06-04	19497093
[Treatment of sleep disorders during pregnancy and breast feeding].	2006-11-23	17115673
Mucosal delivery of cytotoxic therapeutic agents: response of rat nasal mucosa to microencapsulated ethopropazine HCl enantiomer.	2005-11	16421084
Interaction of protonated anticancer thiazines with water-insoluble phospholipids and antineoplastic agents.	2002-05-17	12014679
Citalopram in fatal poisoning cases.	2002-03-28	11955823

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 `Mon Mar 31 18:25:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:53 GMT 2025`
Record UNII	242Z0PM79Y
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PROPIOMAZINE

Official Name

English

CB 1678

Preferred Name

English

2-PROPIONYL-10-(2-(DIMETHYLAMINO)PROPYL)PHENOTHIAZINE

Systematic Name

English

PROPIOMAZINE [VANDF]

Common Name

English

PROPIOMAZINE [MART.]

Common Name

English

PROPIOMAZINE [USAN]

Common Name

English

CB-1678

Code

English

propiomazine [INN]

Common Name

English

Propiomazine [WHO-DD]

Common Name

English

PROPIOMAZINE [MI]

Common Name

English

PROPIOMAZINE [HSDB]

Common Name

English

WY-1359

Code

English

1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl]-1-propanone

Systematic Name

English

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

Systematic Name

English

(±)-PROPIOMAZINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710