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Details

Stereochemistry RACEMIC
Molecular Formula C17H28N2O2
Molecular Weight 292.4164
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMBUCETAMIDE

SMILES

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

InChI

InChIKey=WUSAVCGXMSWMQM-UHFFFAOYSA-N
InChI=1S/C17H28N2O2/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)

HIDE SMILES / InChI
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 ( + / - )

Description

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.

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
Neomeritine

Approved Use

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

Launch Date

-4.65609589E11
PubMed

PubMed

TitleDatePubMed
The effects of ambucetamide on human myometrial and other preparations, and its antagonism to the menstrual stimulant.
1960 Mar
Patents

Patents

US20030236236
2
US5719197
2
US5980882
2
US6562363
4

Sample Use Guides

In Vivo Use Guide
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 Sat Dec 16 17:57:57 UTC 2023
Edited
by admin
on Sat Dec 16 17:57:57 UTC 2023
Record UNII
131B408RZI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMBUCETAMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
(±)-AMBUCETAMIDE
Common Name English
A-16
Code English
AMBUCETAMIDE [MART.]
Common Name English
ambucetamide [INN]
Common Name English
AMBUCETAMIDE, (±)-
Common Name English
Ambucetamide [WHO-DD]
Common Name English
AMBUCETAMIDE [MI]
Common Name English
2-(DIBUTYLAMINO)-2-(P-METHOXYPHENYL)ACETAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29698
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
208-278-7
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
MERCK INDEX
m29
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4057760
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
WIKIPEDIA
AMBUCETAMIDE
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
NCI_THESAURUS
C80975
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
PUBCHEM
10616
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
SMS_ID
100000087669
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
DRUG CENTRAL
148
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
CAS
519-88-0
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
EVMPD
SUB05400MIG
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104638
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
FDA UNII
131B408RZI
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
INN
627
Created by admin on Sat Dec 16 17:57:57 UTC 2023 , Edited by admin on Sat Dec 16 17:57:57 UTC 2023
PRIMARY
Related Record Type Details
Structure of AMBUCETAMIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of AMBUCETAMIDE, (S)-
ENANTIOMER -> RACEMATE
Structure of AMBUCETAMIDE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of AMBUCETAMIDE
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