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Details

Stereochemistry MIXED
Molecular Formula C19H32NO2
Molecular Weight 306.4629
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of VALETHAMATE

SMILES

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

InChI

InChIKey=UPPMZCXMQRVMME-UHFFFAOYSA-N
InChI=1S/C19H32NO2/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/q+1

HIDE SMILES / InChI

Description
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.

Approval Year

T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
VALETHAMATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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: Page: Page 13676
healthy, 20-30
n = 50
Health Status: healthy
Condition: Labour
Age Group: 20-30
Sex: F
Population Size: 50
Sources: Page: Page 13676
60 mg single, intravenous|intramuscular
Toxic dose
Dose: 60 mg
Route: intravenous|intramuscular
Route: single
Dose: 60 mg
Sources: Page: Page 13674
healthy
Health Status: healthy
Condition: Labour
Sex: F
Sources: 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: Page: Page 13674
AEs

AEs

AESignificanceDosePopulation
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: Page: Page 13674
healthy
Health Status: healthy
Condition: Labour
Sex: F
Sources: 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: Page: Page 13674
healthy
Health Status: healthy
Condition: Labour
Sex: F
Sources: Page: Page 13674
PubMed

PubMed

TitleDatePubMed
Drotaverine hydrochloride vs. valethamate bromide in acceleration of labor.
2001 Sep
Comparison of domiciliary and institutional delivery-care practices in rural Rajasthan, India.
2009 Apr
Meperidine versus valethamate bromide in shortening the duration of active labor.
2009 Nov
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Valethamate bromide: Is there any proof of efficacy and safety for its use in labor?
2010 Jan
Valethamate bromide: Conflicting evidence and continuing use.
2010 Jul
Author's reply.
2010 Jul
Patents

Patents

Sample Use Guides

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).
Name Type Language
VALETHAMATE
WHO-DD  
Common Name English
N,N-DIETHYL-N-METHYL-2-(3-METHYL-2-PHENYLVALERYLOXY)ETHYLAMMONIUM
Systematic Name English
VALETHAMATE CATION
Common Name English
Valethamate [WHO-DD]
Common Name English
ETHANAMINIUM, N,N-DIETHYL-N-METHYL-2-((3-METHYL-1-OXO-2-PHENYLPENTYL)OXY)-
Systematic Name English
N,N-DIETHYL-N-METHYL-2-((3-METHYL-1-OXO-2-PHENYLPENTYL)OXY)ETHANAMINIUM
Systematic Name English
VALETHAMATE ION
Common Name English
Classification Tree Code System Code
WHO-ATC A03AX14
Created by admin on Fri Dec 15 20:42:31 UTC 2023 , Edited by admin on Fri Dec 15 20:42:31 UTC 2023
Code System Code Type Description
FDA UNII
D64S64QVX7
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PRIMARY
EVMPD
SUB15684MIG
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PRIMARY
DRUG BANK
DB13497
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PUBCHEM
5648
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MESH
C004904
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DRUG CENTRAL
2800
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PRIMARY
CAS
16376-74-2
Created by admin on Fri Dec 15 20:42:31 UTC 2023 , Edited by admin on Fri Dec 15 20:42:31 UTC 2023
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SMS_ID
100000076964
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