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Details

Stereochemistry MIXED
Molecular Formula C28H42N4O9
Molecular Weight 578.6545
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIFEBARBAMATE

SMILES

CCCCOCC(CN1C(=O)N(CC(COCCCC)OC(N)=O)C(=O)C(CC)(C1=O)C2=CC=CC=C2)OC(N)=O

InChI

InChIKey=GJJRIOLBUILIGK-UHFFFAOYSA-N
InChI=1S/C28H42N4O9/c1-4-7-14-38-18-21(40-25(29)35)16-31-23(33)28(6-3,20-12-10-9-11-13-20)24(34)32(27(31)37)17-22(41-26(30)36)19-39-15-8-5-2/h9-13,21-22H,4-8,14-19H2,1-3H3,(H2,29,35)(H2,30,36)

HIDE SMILES / InChI
Difebarbamate is a barbituric acid derivative. It is a hypnotic drug. Difebarbamate is a component of Tetrabamate complex, which was introduced for clinical use in the treatment of alcoholism and various types of drug dependence. After oral administration of difebarbamate, the compound was completely metabolized and three metabolic pathways were observed: oxidation of Cl of the n-butyl chain which leads to the oxygen dealkylation; hydrolysis of the carbamoyloxy group; oxidation of the benzene ring in position 4. Tetrabamate can induce hepatotoxicity, probably due to an idiosyncratic metabolic mechanism. Despite restrictions on its indications and treatment duration introduced in 1997, cases of severe liver damage have continued to be notified in France.

Approval Year

PubMed

PubMed

TitleDatePubMed
Possible association between poor metabolism of mephenytoin and hepatotoxicity caused by Atrium, a fixed combination preparation containing phenobarbital, febarbamate and difebarbamate.
1994 Dec

Sample Use Guides

Single dose - 25 mg/kg
Route of Administration: Oral
Name Type Language
DIFEBARBAMATE
INN   MART.   WHO-DD  
INN  
Official Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 1,3-BIS(2-((AMINOCARBONYL)OXY)-3-BUTOXYPROPYL)-5-ETHYL-5-PHENYL-
Systematic Name English
difebarbamate [INN]
Common Name English
1,3-BIS(3-BUTOXY-2-HYDROXYPROPYL)-5-ETHYL-5-PHENYLBARBITURIC ACID DICARBAMATE ESTER
Common Name English
Difebarbamate [WHO-DD]
Common Name English
DIFEBARBAMATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
Code System Code Type Description
RXCUI
23020
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY RxNorm
PUBCHEM
71880
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
DRUG CENTRAL
876
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105563
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
SMS_ID
100000083131
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
INN
1240
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
EVMPD
SUB07116MIG
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
FDA UNII
7EE4K616KK
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
NCI_THESAURUS
C77252
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID00864624
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
WIKIPEDIA
Difebarbamate
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
CAS
15687-09-9
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-778-3
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY
MESH
C007383
Created by admin on Fri Dec 15 16:36:31 GMT 2023 , Edited by admin on Fri Dec 15 16:36:31 GMT 2023
PRIMARY