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]
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Therapeutic Class

Hypnotics and Sedatives

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.