Details of the Drug

General Information of Drug (ID: DMQ314B)

Drug Name
Hexobarbital
Synonyms
Barbidorm; Citodon; Citopan; Cyclonal; Cyclopan; Dorico; Enhexymal; Enhexymalum; Esobarbitale; Evipal; Evipan; Hexabarbital;Hexobarbitalum; Hexobarbitone; Hexobarbitonum; Methexenyl; Methylhexabarbital; Methylhexabital; Narcosan; Noctivane; Sombucaps; Sombulex; Somnalert; Esobarbitale [DCIT]; Esobarbitale [Italian]; Hexanastab oral; Sodium hexobarbital; Citopan (TN); Evipan (TN); Hexenal (barbiturate); Hexobarbital (VAN); Hexobarbital [INN:JAN]; Hexobarbitalum [INN-Latin]; Hexobarbital (JAN/INN); N-Methyl-5-cyclohexenyl-5-methylbarbituric acid; (+-)-Hexobarbital; 1,5-Dimethyl-5-(1-cyclohexenyl)barbituric acid; 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl; 5-(1-CYCLOHEXEN-1-YL)-1,5-DIMETHYLBARBITURIC ACID; 5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-(1-Cyclohexenyl)-1,5-dimethylbarbituric acid; 5-(1-Cyclohexenyl-1)-1-methyl-5-methylbarbituric acid; 5-(cyclohex-1-en-1-yl)-1,5-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione; 5-(delta-1,2-Cyclohexenyl)-5-methyl-N-methyl-barbitursaeure [German]; 5-(delta-1,2-cyclohexenyl)-5-methyl-N-methyl-barbitursaeure; 5-(delta.-1,2-cyclohexenyl)-5-methyl-N-methyl-barbitursaeure; 5-cyclohex-1-en-1-yl-1,5-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; 5-cyclohex-1-en-1-yl-2-hydroxy-1,5-dimethylpyrimidine-4,6(1H,5H)-dione
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Therapeutic Class
Hypnotics and Sedatives
Affected Organisms
Humans and other mammals
ATC Code
N01AF02: Hexobarbital
N01AF: Barbiturates, plain
N01A: ANESTHETICS, GENERAL
N01: ANESTHETICS
N: NERVOUS SYSTEM
N05CA16: Hexobarbital
N05CA: Barbiturates, plain
N05C: HYPNOTICS AND SEDATIVES
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 236.27
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability
95% of drug becomes completely available to its intended biological destination(s) [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.4 mL/min/kg [4]
Elimination
0.5% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.9 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.231 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.53% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 640 mg/mL [2]
Chemical Identifiers
Formula
C12H16N2O3
IUPAC Name
5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
Canonical SMILES
CC1(C(=O)NC(=O)N(C1=O)C)C2=CCCCC2
InChI
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
Cross-matching ID
PubChem CID
3608
ChEBI ID
CHEBI:5706
CAS Number
56-29-1
UNII
AL8Z8K3P6S
DrugBank ID
DB01355
TTD ID
D00ETS
INTEDE ID
DR0809

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 [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [8]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [9]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Hexobarbital, 2008. eduDrugs.
2 BDDCS applied to over 900 drugs
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
7 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.
8 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
9 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.
10 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.