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

General Information of Drug (ID: DR1254)
Drug Name
Pentobarbital
Synonyms
Pentabarbital; Pentabarbitone; Pentobarbital (VAN); Pentobarbitale [DCIT]; Pentobarbitalum; Pentobarbitone; Pentobarbitone (VAN); Pentobarbiturate; Pentobarbituric acid; Rivadorm; pentobarbital; 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; Aethaminalum; Dorsital; Ethaminal; Mebubarbital; Mebumal; Nebralin; Nembutal; Nembutal (VAN); Neodorm; Neodorm (VAN); Neodorm (new); 5-Ethyl-5-(1-methylbutyl)barbituric acid; 5-Ethyl-5-(1-methylbutyl)malonylurea; 5-Ethyl-5-(sec-pentyl)barbituric acid; 76-74-4
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 226.27 Topological Polar Surface Area 75.3
Heavy Atom Count 16 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4737
PubChem SID
9626 ; 88629 ; 4875675 ; 7687719 ; 7847565 ; 8150116 ; 8152908 ; 10535336 ; 11336167 ; 11361406 ; 11364680 ; 11367242 ; 11369804 ; 11372904 ; 11374147 ; 11377967 ; 11462378 ; 11485937 ; 11489807 ; 11491598 ; 11492389 ; 11495597 ; 11533361 ; 15196098 ; 26612988 ; 26679656 ; 26750091 ; 29223823 ; 46508399 ; 47291210 ; 47440355 ; 47813402 ; 47885494 ; 48187638 ; 48416394 ; 49874341 ; 50107805 ; 53788844 ; 56313777 ; 57322422 ; 79087870 ; 92308182 ; 99302080 ; 103165831 ; 103858250 ; 103952389 ; 104307283 ; 104826284 ; 117425382 ; 124637312
ChEBI ID
ChEBI:7983
CAS Number
76-74-4
TTD Drug ID
D0F0YZ
Formula
C11H18N2O3
Canonical SMILES
CCCC(C)C1(C(=O)NC(=O)NC1=O)CC
InChI
1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
InChIKey
WEXRUCMBJFQVBZ-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'-hydroxypentobarbital DM001193
94288
Oxidation - Penultimate Oxidation 1 [4]
4-hydroxyphenobarbital DM001192
9785
Oxidation - Hydroxylation 1 [3]
Pentobarbital carboxylic acid DM001195 N. A. Oxidation - Oxidation 1 [3]
Phenobarbitone glucoside DM001194
115321
Conjugation - Glucuronidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001974 Pentobarbital 4-hydroxyphenobarbital Oxidation - Hydroxylation CYP2C9 ... [3]
MR001975 Pentobarbital 3'-hydroxypentobarbital Oxidation - Penultimate Oxidation Unclear [4]
MR001976 Pentobarbital Phenobarbitone glucoside Conjugation - Glucuronidation Unclear [3]
MR001977 Pentobarbital Pentobarbital carboxylic acid Oxidation - Oxidation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Pentobarbital was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP2C19 polymorphism effect on phenobarbitone. Pharmacokinetics in Japanese patients with epilepsy: analysis by population pharmacokinetics Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):821-5. doi: 10.1007/s002280050703.
3 CYP2C19 polymorphism effect on phenobarbitone. Pharmacokinetics in Japanese patients with epilepsy: analysis by population pharmacokinetics. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):821-5.
4 American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2666

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