VALETHAMATE BROMIDE

First approved in 1958

Details

Stereochemistry	MIXED
Molecular Formula	C19H32NO2.Br
Molecular Weight	386.367
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CCC(C)C(C(=O)OCC[N+](C)(CC)CC)C1=CC=CC=C1

InChI

InChIKey=CEJGGHKJHDHLAZ-UHFFFAOYSA-M

InChI=1S/C19H32NO2.BrH/c1-6-16(4)18(17-12-10-9-11-13-17)19(21)22-15-14-20(5,7-2)8-3;/h9-13,16,18H,6-8,14-15H2,1-5H3;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H32NO2
Molecular Weight	306.4629
Charge	1
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1635586
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/valethamate-bromide.html | https://www.ncbi.nlm.nih.gov/pubmed/19664769 | https://www.ncbi.nlm.nih.gov/pubmed/26291425

Valethamate bromide ( sold under many brand names such as Epidosin, Dilaton, Valosin, Valamate, Osdil etc), a quarternary ammonium agent, has been used in augmentation of labor. Valethamate has antimuscarinic action and blocks cholinergic receptors in the ganglia. This action along with the direct action on the smooth muscles of the cervix is thought to help cervical dilatation during labor. Since it is not selective, it exerts anticholinergic side effects such as tachycardia, flushing, cotton mouth and photophobia due to mydriasis. Common side effects are palpitations, increased heart rate, arrhythmia, excessive thirst, reduced bronchial secretions, dry mouth, Photophobia, dry skin, loss of accommodation, slow heart rate, flushing.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1635586	Antagonist 2778
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1635586	Antagonist 2778
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1635586	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Symptomatic relief of gastrointestinal colic, biliary colic, ureteric colic 2 Sources: https://www.medicineindia.org/pharmacology-for-generic/258/valethamate	Primary		Approved 8429	EPIDOSIN Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h OTHER https://www.ijrcog.org/index.php/ijrcog/article/view/1221			VALETHAMATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 mg 2 times / hour multiple, intravenous Highest studied dose Dose: 8 mg, 2 times / hour Route: intravenous Route: multiple Dose: 8 mg, 2 times / hour Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13676	healthy, 20-30 n = 50 Health Status: healthy Condition: Labour Age Group: 20-30 Sex: F Population Size: 50 Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13676	Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13676
60 mg single, intravenous\|intramuscular Toxic dose Dose: 60 mg Route: intravenous\|intramuscular Route: single Dose: 60 mg Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674	healthy Health Status: healthy Condition: Labour Sex: F Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674	Disc. AE: Circulatory failure, Respiratory failure... AEs leading to discontinuation/dose reduction: Circulatory failure (grade 5, very rare) Respiratory failure (grade 5, very rare) Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674

AEs

AE	Significance	Dose	Population
Circulatory failure	grade 5, very rare Disc. AE	60 mg single, intravenous\|intramuscular Toxic dose Dose: 60 mg Route: intravenous\|intramuscular Route: single Dose: 60 mg Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674	healthy Health Status: healthy Condition: Labour Sex: F Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674
Respiratory failure	grade 5, very rare Disc. AE	60 mg single, intravenous\|intramuscular Toxic dose Dose: 60 mg Route: intravenous\|intramuscular Route: single Dose: 60 mg Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674	healthy Health Status: healthy Condition: Labour Sex: F Sources: https://www.jemds.com/data_pdf/3_Sunita%20%20%20%20Ruksa--%20GU.pdf Page: Page 13674

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003VQX
A2B Chem	AB80313
AA Blocks	AA003V7H
ABI Chem	AC1L1KTK
AK Scientific	J10849
AK Scientific	N011
Alfa Chemistry	ACM90222
Ambeed	A439776
AstaTech	A12927
BLD Pharm	BD156285
BOC Sciences	90-22-2
Bide Pharmatech	BD156285
BioSynth	W-100337
BlocksMatrix Scientific	99549
ChemMol	49426181	http://www.chemmol.com/chemmol/49426181.html
Combi-Blocks	QA-0326
Compound Cloud	5648
Compound Cloud	7010
Fluorochem	242202
Hairui	HR135603
Hangzhou APIChem Technology	AC-19311
KeyOrganics	AS-14890
Lab Network	LN00201161
MolPort	MolPort-003-910-566
Molnova	M16487
MuseChem	M087967
Norris Pharm	NSZB-A254230
Ryan Scientific	ML347
Selleck Chemicals	S5038
Sigma Aldrich	S422649
Sigma Aldrich	S422649\|ALDRICH
TargetMol	T0023
TimTec	ST51253716
Toronto Research Chemicals	D477320
Wonderchem	WD06YRV
ZINC	ZINC000002041203	http://zinc15.docking.org/substances/ZINC000002041203
ZINC	ZINC000002041204	http://zinc15.docking.org/substances/ZINC000002041204
ZINC	ZINC000002041205	http://zinc15.docking.org/substances/ZINC000002041205
ZINC	ZINC000002041206	http://zinc15.docking.org/substances/ZINC000002041206
eMolecules	2735611
eNovation Chemicals	D748930
mcule	MCULE-5010342809	https://mcule.com/MCULE-5010342809/

PubMed

Title	Date	PubMed
Drotaverine hydrochloride vs. valethamate bromide in acceleration of labor.	2001 Sep	11543749
Comparison of domiciliary and institutional delivery-care practices in rural Rajasthan, India.	2009 Apr	19489423
Meperidine versus valethamate bromide in shortening the duration of active labor.	2009 Nov	19664769
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Valethamate bromide: Is there any proof of efficacy and safety for its use in labor?	2010 Jan	21808583
Author's reply.	2010 Jul	21350625
A randomised controlled study comparing Drotaverine hydrochloride and Valethamate bromide in the augmentation of labour.	2010 Jul	19644697

Patents

Sample Use Guides

In Vivo Use Guide

Adult- PO- Per tab contains valethamate bromide 10 mg and paracetamol 325 mg: 1 tab 3 times/day. IV/IM- 8-16 mg/day.

Route of Administration: Other

In Vitro Use Guide

The contraction of uterine horns from immature guinea pigs in response to methacholine (isotonic recording) was used for activity evaluztion. The uterine horns were suspended in an organ bath under 1 g resting tension and were superfused with SUND's physiological salt solution at a rate of 2 mi/min . After an equilibration period of 60 rain, 4 cumulative concentration-response curves to methacholine were obtained in each preparation at 60 or 90 min intervals. The first curve served as a control for the following curves which were carried out in the absence or presence of increasing concentrations of a given antagonist (60 or 90 min equilibration time).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:22:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:22:29 GMT 2023`
Record UNII	6XFR940M2A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VALETHAMATE BROMIDE

Common Name

English

Valethamate bromide [WHO-DD]

Common Name

English

VALETHAMATE BROMIDE [JAN]

Common Name

English

3-METHYL-2-PHENYLVALERIC ACID DIETHYL(3-HYDROXYETHYL)METHYLAMMONIUM BROMIDE ESTER

Common Name

English

EPIDOSIN

Common Name

English

VALETHAMATE BROMIDE [MI]

Common Name

English

VALETHAMATE BROMIDE [MART.]

Common Name

English

N,N-DIETHYL-N-METHYL-2-(3-METHYL-2-PHENYLVALERYLOXY)ETHYLAMMONIUM BROMIDE

Systematic Name

English

N,N-DIETHYL-N-METHYL-2-((3-METHYL-1-OXO-2-PHENYLPENTYL)OXY)ETHANAMINIUM BROMIDE

Systematic Name

English

DIETHYL(2-HYDROXYETHYL)METHYLAMMONIUM 3-METHYL-2-PHENYLVALERATE BROMIDE

Systematic Name

English

ETHANAMINIUM, N,N-DIETHYL-N-METHYL-2-((3-METHYL-1-OXO-2-PHENYLPENTYL)OXY)-, BROMIDE (1:1)

Systematic Name

English

3-METHYL-2-PHENYLVALERIC ACID 2-DIETHYLAMINOETHYL ESTER METHYL BROMIDE

Systematic Name

English

RESITAN

Common Name

English

2-DIETHYLAMINOETHYL 2-PHENYL-3-METHYLVALERATE METHYL BROMIDE

Systematic Name

English

2-PHENYL-3-METHYLVALERIC ACID .BETA.-(DIETHYLAMINO)ETHYL ESTER BROMOMETHYLATE

Common Name

English

Code System Code Type Description

CAS

90-22-2