Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0174)
Drug Name
Barbital
Synonyms
Barbital [VAN]; Barbitale [DCIT]; Barbitalum [INN-Latin]; Barbitone; Barbitonum; Barbituric acid, 5,5-diethyl-; Diemal; Diemalum; Diethyl-barbituric acid; Diethylbarbitone; Diethylbarbituric acid; Diethylmalonylurea; Dormonal; Ethylbarbital; Hypnogene; Kyselina 5,5-diethylbarbiturova; Malonal; Medinal; Sedeval; Uronal; Veroletten; Verolettin; Veronal; Vesperal; barbital; 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5-diethyl-; 5,5-Diethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5,5-Diethylbarbituric acid; 57-44-3; DEBA
Indication Insomnia [ICD11: 7A00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 184.19 Topological Polar Surface Area 75.3
Heavy Atom Count 13 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2294
PubChem SID
90340 ; 589068 ; 841531 ; 5611996 ; 5972305 ; 7848803 ; 8151540 ; 10527896 ; 11533956 ; 15219736 ; 24859202 ; 24891513 ; 29215357 ; 29215358 ; 29221466 ; 46508979 ; 47365376 ; 48334676 ; 48415603 ; 49874104 ; 50176612 ; 56459416 ; 57321239 ; 57648640 ; 58694180 ; 103165760 ; 104300174 ; 118189912 ; 124892181 ; 125332012 ; 125736552 ; 126677738 ; 127897641 ; 134338564 ; 134970868 ; 137003152 ; 137204186 ; 139051997 ; 144076045 ; 144205203 ; 152042447 ; 160964740 ; 163120017 ; 164836116 ; 164836117 ; 165319864 ; 170465829 ; 175265443 ; 175442207 ; 175611463
ChEBI ID
ChEBI:31252
CAS Number
57-44-3
TTD Drug ID
D0E0WQ
Formula
C8H12N2O3
Canonical SMILES
CCC1(C(=O)NC(=O)NC1=O)CC
InChI
1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
InChIKey
FTOAOBMCPZCFFF-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5-(beta-hydroxyethyl)-5-ethylbarbituric acid DM001606
95239
Oxidation - Oxidative Degradation 1 [3]
5-ethylbarbituric acid DM001607
17292
Oxidation - Oxidative Degradation 1 [3]
5-ethyldialuric acid DM001605
13229393
Oxidation - Oxidative Degradation 1 [3]
Diethyl-malonic acid monoureid DM001608
6455724
Hydrolysis - Hydrolysis 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000344 Barbital 5-ethyldialuric acid Oxidation - Oxidative Degradation Unclear [3]
MR000345 Barbital 5-(beta-hydroxyethyl)-5-ethylbarbituric acid Oxidation - Oxidative Degradation Unclear [3]
MR000346 Barbital 5-ethylbarbituric acid Oxidation - Oxidative Degradation Unclear [3]
MR000347 Barbital Diethyl-malonic acid monoureid Hydrolysis - Hydrolysis Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 The history of barbiturates a century after their clinical introduction. Neuropsychiatr Dis Treat. 2005 Dec;1(4):329-43.
2 Effects of cytochrome P450 (CYP)2C19 polymorphisms on pharmacokinetics of phenobarbital in neonates and infants with seizures. Arch Dis Child. 2012 Jun;97(6):569-72.
3 METABOLISM OF BARBITAL BY STREPTOMYCES MEDITERRANEI Appl Microbiol. 1965 Jul;13(4):600-4. doi: 10.1128/am.13.4.600-604.1965.

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