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

General Information of Drug (ID: DR0809)
Drug Name
VA-10872
Synonyms
Barbidorm; Citodon; Citopan; Cyclonal; Cyclopan; Hexobarbital; Dorico; Enhexymal; Enhexymalum; Esobarbitale; Esobarbitale [DCIT]; Esobarbitale [Italian]; Evipal; Evipan; Hexabarbital; Hexanastab oral; Hexenal (barbiturate); Hexobarbital (VAN); Hexobarbitalum; Hexobarbitalum [INN-Latin]; Hexobarbitone; Hexobarbitonum; Methexenyl; Methylhexabarbital; Methylhexabital; Narcosan; Noctivane; Sodium hexobarbital; Sombucaps; Sombulex; Somnalert; 5-(1-CYCLOHEXEN-1-YL)-1,5-DIMETHYLBARBITURIC ACID; 56-29-1
Indication Anaesthesia [ICD11: 8E22] Preclinical [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 236.27 Topological Polar Surface Area 66.5
Heavy Atom Count 17 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3608
PubChem SID
13888 ; 114792 ; 4911070 ; 7848134 ; 8147019 ; 8152276 ; 10527424 ; 15415683 ; 24895418 ; 26754503 ; 29215369 ; 29222734 ; 46508777 ; 47194291 ; 47959959 ; 48416081 ; 49873997 ; 57309846 ; 57321894 ; 57654225 ; 79698506 ; 92714691 ; 103165870 ; 104304001 ; 104903183 ; 117838626 ; 118856010 ; 124813353 ; 124892192 ; 125309499 ; 125488787 ; 126623945 ; 129440427 ; 134337977 ; 134972602 ; 135194968 ; 135300355 ; 137101291 ; 139408774 ; 144205214 ; 144205215 ; 144236491 ; 160964645 ; 163050404 ; 164815041 ; 170250749 ; 170465860 ; 176267018 ; 179225803 ; 179296095
ChEBI ID
ChEBI:5706
CAS Number
56-29-1
TTD Drug ID
D00ETS
Formula
C12H16N2O3
Canonical SMILES
CC1(C(=O)NC(=O)N(C1=O)C)C2=CCCCC2
InChI
1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)
InChIKey
UYXAWHWODHRRMR-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
3'-Hydroxyhexobarbital DM006498
439898
Oxidation - 3'-hydroxylation 1 [5]
Epoxy-hexobarbital DM006501
171784
Unclear 1 [5]
3'-Hydroxyhexobarbital O-glucuronide DM007039 N. A. Conjugation - Glucuronidation 2 [5]
3'-Oxohexobarbitall DM006499
439745
Oxidation - Oxidationn 2 [5]
Hexobarbital dihydrodiol derivative DM006502 N. A. Unclear 2 [5]
1,5-Dimethyl barbituric acid DM014798 N. A. Unclear 3 [5]
Hexobarbital glutathione conjugate derivative DM006500 N. A. Conjugation - Glutathione conjugation 3 [5]
1,5-dimethylbarbituric acid DM007038
151461
Unclear 4 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006991 VA-10872 3'-Hydroxyhexobarbital Oxidation - 3'-hydroxylation CYP2C9 ... [5]
MR006996 VA-10872 Epoxy-hexobarbital Unclear Unclear [5]
MR006992 3'-Hydroxyhexobarbital 3'-Oxohexobarbitall Oxidation - Oxidationn . [5]
MR006995 3'-Hydroxyhexobarbital 3'-Hydroxyhexobarbital O-glucuronide Conjugation - Glucuronidation UGT [5]
MR006997 Epoxy-hexobarbital Hexobarbital dihydrodiol derivative Unclear Unclear [5]
MR006993 3'-Oxohexobarbitall Hexobarbital glutathione conjugate derivative Conjugation - Glutathione conjugation GST [5]
MR006998 Hexobarbital dihydrodiol derivative 1,5-Dimethyl barbituric acid Unclear Unclear [5]
MR006994 Hexobarbital glutathione conjugate derivative 1,5-dimethylbarbituric acid Unclear Unclear [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
References
1 Duration of hexobarbital-induced sleep and monoamine oxidase activities in rat brain: focus on the behavioral activity and on the free-radical oxidation. Gen Physiol Biophys. 2016 Apr;35(2):175-83.
2 Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Stereoselective hexobarbital 3'-hydroxylation by CYP2C19 expressed in yeast cells and the roles of amino acid residues at positions 300 and 476. Chirality. 2007 Jul;19(7):550-8.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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