Details of the Drug

General Information of Drug (ID: DMJ8NMC)

• Drug Name: Barbital
• Synonyms: Barbitale; Barbitalum; Barbitone; Barbitonum; DEBA; Diemal; Diemalum; Diethylbarbitone; Diethylmalonylurea; Dormileno; Dormonal; Ethylbarbital; Hypnogene; Malonal; Medinal; Sedeval; Uronal; Veroletten; Verolettin; Veronal; Vesperal; Barbital Faes Brand; Barbitale [DCIT]; Diethylbarbituric acid; Faes Brand of Barbital; Barbital (TN); Barbital (VAN); Barbital [INN:JAN]; Barbitalum [INN-Latin]; Veronal (TN); Barbital (JP15/INN); Kyselina 5,5-diethylbarbiturova; Kyselina 5,5-diethylbarbiturova [Czech]; 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5-diethyl-(9CI); 5,5-Diethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5,5-Diethylbarbituric acid; 5,5-diethyl-1,3-diazinane-2,4,6-trione; 5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione; 7979P

Indication

Disease Entry	ICD 11	Status	REF
Insomnia	7A00-7A0Z	Approved	[1]

• Therapeutic Class: Hypnotics and Sedatives
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 184.19
  Topological Polar Surface Area (xlogp); 0.6
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 3
• Chemical Identifiers:
  Formula: C8H12N2O3
  IUPAC Name: 5,5-diethyl-1,3-diazinane-2,4,6-trione
  Canonical SMILES: CCC1(C(=O)NC(=O)NC1=O)CC
  InChI: 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
• Cross-matching ID:
  PubChem CID: 2294
  ChEBI ID: CHEBI:31252
  CAS Number: 57-44-3
  DrugBank ID: DB01483
  TTD ID: D0E0WQ
  INTEDE ID: DR0174

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor alpha-1 (GABRA1)	TT1MPAY	GBRA1_HUMAN	Antagonist	[1], [2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Mephenytoin 4-hydroxylase (CYP2C19) Main DME	DEGTFWK	CP2CJ_HUMAN	Substrate	[3]

References

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• [2] Effect of barbiturates on polyphosphoinositide biosynthesis and protein kinase C activity in synaptosomes. Neuropharmacology. 1989 Dec;28(12):1317-23.
• [3] 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.
• [4] High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
• [5] Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
• [6] Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
• [7] CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
• [8] Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
• [9] Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
• [10] Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
• [11] A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
• [12] Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
• [13] Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
• [14] Zolpidem, a selective GABA(A) receptor alpha1 subunit agonist, induces comparable Fos expression in oxytocinergic neurons of the hypothalamic paraventricular and accessory but not supraoptic nuclei in the rat.Brain Res Bull.2006 Dec 11;71(1-3):200-7.
• [15] Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (... J Med Chem. 2005 Apr 21;48(8):3051-9.
• [16] 3-demethoxy-3-glycosylaminothiocolchicines: Synthesis of a new class of putative muscle relaxant compounds. J Med Chem. 2006 Sep 7;49(18):5571-7.
• [17] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.