General Information of Drug (ID: DR1275)
Drug Name
Phenobarbital
Synonyms
Phenaemal; Phenemal; Phenobarbitol; Phenobarbitone; Phenobarbituric acid; Phenobarbyl; Phenolurio; Phenonyl; Phenoturic; Phenylethylbarbiturate; Phenylethylbarbituric acid; Phenylethylmalonylurea; Phenyral; Polcominal; Sedonettes; Adonal; Aphenylbarbit; Aphenyletten; Barbiphenyl; Cabronal; Cratecil; Dezibarbitur; Dormiral; Ensodorm; Fenobarbital; Gardenal; Glysoletten; Hypnogen; Hysteps; Lepinaletten; Lubrokal; Lumesettes; Luminal; Lumofridetten; Neurobarb; Solfoton; Sombutol; Somnolens; Somnoletten; Somnosan; phenobarbital; Nunol
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 232.23 Topological Polar Surface Area 75.3
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4763
PubChem SID
9638 ; 75216 ; 419552 ; 590135 ; 607900 ; 4437710 ; 7538915 ; 7847572 ; 7980291 ; 8150142 ; 8152924 ; 10524254 ; 10589109 ; 11109645 ; 11336162 ; 11361401 ; 11462373 ; 11533360 ; 14822944 ; 24898226 ; 29215458 ; 29215459 ; 29223847 ; 46505776 ; 47365286 ; 48334587 ; 48414299 ; 48414897 ; 48416415 ; 48423927 ; 49854358 ; 50754225 ; 51087546 ; 53786889 ; 56310640 ; 56310993 ; 56312250 ; 56312902 ; 56313381 ; 56313456 ; 56313891 ; 56314430 ; 56314439 ; 56314440 ; 57288737 ; 85174399 ; 93167079 ; 99302075 ; 103165722 ; 103932141
ChEBI ID
ChEBI:8069
CAS Number
50-06-6
TTD Drug ID
D0Y7RW
Formula
C12H12N2O3
Canonical SMILES
CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2
InChI
1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
InChIKey
DDBREPKUVSBGFI-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
4-hydroxyphenobarbital DM001192
9785
Oxidation - 4-Hydroxylation 1 [11]
Mephobarbital DM001234
8271
Conjugation - Methylation 1 [12]
Phenobarbital N-glucuronide DM001232
101704422
Conjugation - Conjugation 2 [12]
Phenobarbital O-sulfate DM001233
71371485
Conjugation - Conjugation 2 [12]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002023 Phenobarbital 4-hydroxyphenobarbital Oxidation - 4-Hydroxylation CYP2C19 ... [11]
MR002024 Phenobarbital Mephobarbital Conjugation - Methylation CYP2C19 ... [12]
MR002021 4-hydroxyphenobarbital Phenobarbital N-glucuronide Conjugation - Conjugation Unclear [12]
MR002022 4-hydroxyphenobarbital Phenobarbital O-sulfate Conjugation - Conjugation Unclear [12]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[8]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[9]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[10]
⏷ Show the Full List of 9  DME(s)
References
1 Phenobarbital was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58.
3 Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51.
4 Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9.
5 Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor. J Pharmacol Exp Ther. 2004 Feb;308(2):495-501.
6 Phenobarbital induces monkey brain CYP2E1 protein but not hepatic CYP2E1, in vitro or in vivo chlorzoxazone metabolism. Eur J Pharmacol. 2006 Dec 15;552(1-3):151-8.
7 Clinically important drug interactions potentially involving mechanism-based inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring. Ther Drug Monit. 2007 Dec;29(6):687-710.
8 Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line. Am J Respir Cell Mol Biol. 2000 Mar;22(3):360-6.
9 Regulation of human liver cytochromes P-450 in family 3A in primary and continuous culture of human hepatocytes. Hepatology. 1993 Nov;18(5):1254-62.
10 Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31.
11 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.
12 DrugBank(Pharmacology-Metabolism)Phenobarbital

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.