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Details

Stereochemistry RACEMIC
Molecular Formula C17H28N2O2.ClH
Molecular Weight 328.877
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMBUCETAMIDE HYDROCHLORIDE

SMILES

Cl.CCCCN(CCCC)C(C(N)=O)C1=CC=C(OC)C=C1

InChI

InChIKey=FZOGOYCDAVNSFE-UHFFFAOYSA-N
InChI=1S/C17H28N2O2.ClH/c1-4-6-12-19(13-7-5-2)16(17(18)20)14-8-10-15(21-3)11-9-14;/h8-11,16H,4-7,12-13H2,1-3H3,(H2,18,20);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H28N2O2
Molecular Weight 292.4164
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Ambucetamide is an antispasmodic found to be particularly effective for the relief of menstrual pain. It was given the number R 5. Launched in April 1955 under the brand name Neomeritine, it is still on the market today.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Neomeritine

Approved Use

An antispasmodic found to be particularly effective for the relief of menstrual pain.

Launch Date

1955
PubMed

PubMed

TitleDatePubMed
Studies with a uterine antispasmodic, ambucetamide.
1957 Sep
The effects of ambucetamide on human myometrial and other preparations, and its antagonism to the menstrual stimulant.
1960 Mar
Rapid spectrophotometric determination of saccharin in soft drinks and pharmaceuticals using Azure B as reagent.
1983 Aug
Determination of embutramide in biological matrices by gas chromatography with nitrogen-phosphorus detection.
1994 Nov 4
Patents

Sample Use Guides

Dogs: In general, doses of 1.0 to 10.0 mg/Kg of ambucetamide produced a drop in tone in the majority of the animals and had no effect upon the frequency of contractions. In about 50% of the dogs there was an increase in the amplitude of contractions at doses of 1.0 and 5.0 mg/Kg, but at a dose of 10.0 mg/Kg the majority showed a decrease in the amplitude of contractions.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The effect of ambucetamide on the isolated rat uterus was studied by a modification of the method of Magnus. The isolated uterus was suspended in a Ringer Tyrode solution modified according to Smith and maintained at 37.5.
Ambucetamide produced a decrease in the amplitude of contraction starting in most instances at a bath concentration of 0.025 mg/cc. This effect was quite marked at a concentration of 0.05 mg/cc. It produced a marked decrease in the frequency of contractions starting with a bath concentration of 0.125 mg/cc. No decrease in tone was noted at concentrations less than 0.025 mg/cc.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:00:15 GMT 2023
Edited
by admin
on Fri Dec 15 19:00:15 GMT 2023
Record UNII
2M010V3MAJ
Record Status Validated (UNII)
Record Version
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Name Type Language
AMBUCETAMIDE HYDROCHLORIDE
WHO-DD  
Common Name English
BENZENEACETAMIDE, .ALPHA.-(DIBUTYLAMINO)-4-METHOXY-, HYDROCHLORIDE (1:1)
Systematic Name English
BENZENEACETAMIDE, .ALPHA.-(DIBUTYLAMINO)-4-METHOXY-, MONOHYDROCHLORIDE
Common Name English
Ambucetamide hydrochloride [WHO-DD]
Common Name English
2-(DIBUTYLAMINO)-2-(P-METHOXYPHENYL)ACETAMIDE HYDROCHLORIDE
Common Name English
AMBUCETAMIDE HYDROCHLORIDE, (±)-
Common Name English
AMBUCETAMIDE HCL
Common Name English
Code System Code Type Description
FDA UNII
2M010V3MAJ
Created by admin on Fri Dec 15 19:00:15 GMT 2023 , Edited by admin on Fri Dec 15 19:00:15 GMT 2023
PRIMARY
CAS
172343-32-7
Created by admin on Fri Dec 15 19:00:15 GMT 2023 , Edited by admin on Fri Dec 15 19:00:15 GMT 2023
PRIMARY
EVMPD
SUB00428MIG
Created by admin on Fri Dec 15 19:00:15 GMT 2023 , Edited by admin on Fri Dec 15 19:00:15 GMT 2023
PRIMARY
SMS_ID
100000085128
Created by admin on Fri Dec 15 19:00:15 GMT 2023 , Edited by admin on Fri Dec 15 19:00:15 GMT 2023
PRIMARY
PUBCHEM
71587573
Created by admin on Fri Dec 15 19:00:15 GMT 2023 , Edited by admin on Fri Dec 15 19:00:15 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY