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Identification
NameMethylphenobarbital
Accession NumberDB00849  (APRD00047)
Typesmall molecule
Groupsapproved
Description

A barbiturate that is metabolized to phenobarbital. It has been used for similar purposes, especially in epilepsy, but there is no evidence mephobarbital offers any advantage over phenobarbital. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
EnphenemalNot AvailableIS
MephobarbitalNot AvailableJAN
MephobarbitoneNot AvailableNot Available
MéthylphénobarbitalFrenchINN
MethylphenobarbitalGermanINN
MethylphenobarbitalumLatinINN
MethylphenobarbitoneNot AvailableIS
MetilfenobarbitalSpanishINN
MetilfenobarbitaleNot AvailableDCIT
SaltsNot Available
Brand names
NameCompany
MebaralLundbeck A/S
MephyltalettenNot Available
PhemitonNot Available
PhemitoneNot Available
PhenmitonNot Available
ProminalNot Available
Brand mixtures
Brand NameIngredients
DintoinaleMethylphenobarbital and Phenytoin
MebroinMethylphenobarbital and Phenytoin
Categories
CAS number115-38-8
WeightAverage: 246.2619
Monoisotopic: 246.100442324
Chemical FormulaC13H14N2O3
InChI KeyInChIKey=ALARQZQTBTVLJV-UHFFFAOYSA-N
InChI
InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)
IUPAC Name
5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione
SMILES
CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1
Mass Specshow(8.57 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassDiazines
SubclassPyrimidines and Pyrimidine Derivatives
Direct parentBarbituric Acid Derivatives
Alternative parentsUreides; Diazinanes; N-substituted Carboxylic Acid Imides; Benzene and Substituted Derivatives; Tertiary Carboxylic Acid Amides; N-unsubstituted Carboxylic Acid Imides; Secondary Carboxylic Acid Amides; Tertiary Amines; Carboxylic Acids; Polyamines
Substituentsureide; 1,3-diazinane; carboxylic acid imide, n-substituted; benzene; tertiary carboxylic acid amide; carboxylic acid imide, n-unsubstituted; carboxamide group; tertiary amine; secondary carboxylic acid amide; carboxylic acid derivative; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
Pharmacology
IndicationFor the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy.
PharmacodynamicsMethylphenobarbital, a barbiturate, is used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain. Barbiturates act as nonselective depressants of the central nervous system (CNS), capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. In sufficiently high therapeutic doses, barbiturates induce anesthesia.
Mechanism of actionMethylphenobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
AbsorptionApproximately 50% of an oral dose of mephobarbital is absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding70-76%
Metabolism

Hepatic, primarily by the hepatic microsomal enzyme system. About 75% of a single oral dose of mephobarbital is metabolized to phenobarbital in 24 hours.

SubstrateEnzymesProduct
Methylphenobarbital
    PhenobarbitalDetails
    Route of eliminationNot Available
    Half life34 (range 11-67) hours
    ClearanceNot Available
    ToxicityNot Available
    Affected organisms
    • Humans and other mammals
    PathwaysNot Available
    SNP Mediated EffectsNot Available
    SNP Mediated Adverse Drug ReactionsNot Available
    ADMET
    Predicted ADMET features
    Property Value Probability
    Human Intestinal Absorption + 0.9952
    Blood Brain Barrier + 0.9859
    Caco-2 permeable + 0.5674
    P-glycoprotein substrate Non-substrate 0.6107
    P-glycoprotein inhibitor I Non-inhibitor 0.5213
    P-glycoprotein inhibitor II Non-inhibitor 0.8987
    Renal organic cation transporter Non-inhibitor 0.8913
    CYP450 2C9 substrate Non-substrate 0.7897
    CYP450 2D6 substrate Non-substrate 0.9138
    CYP450 3A4 substrate Non-substrate 0.6613
    CYP450 1A2 substrate Non-inhibitor 0.857
    CYP450 2C9 substrate Non-inhibitor 0.6815
    CYP450 2D6 substrate Non-inhibitor 0.9404
    CYP450 2C19 substrate Non-inhibitor 0.7403
    CYP450 3A4 substrate Non-inhibitor 0.935
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9254
    Ames test Non AMES toxic 0.727
    Carcinogenicity Non-carcinogens 0.754
    Biodegradation Not ready biodegradable 0.9668
    Rat acute toxicity 2.6756 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.9848
    hERG inhibition (predictor II) Non-inhibitor 0.8733
    Pharmacoeconomics
    ManufacturersNot Available
    Packagers
    Dosage forms
    FormRouteStrength
    TabletOral
    Prices
    Unit descriptionCostUnit
    Mentax 1% cream4.0USDg
    Mebaral 100 mg tablet1.73USDtablet
    Mebaral 50 mg tablet1.28USDtablet
    Mebaral 32 mg tablet0.87USDtablet
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    PatentsNot Available
    Properties
    Statesolid
    Experimental Properties
    PropertyValueSource
    melting point176 °CPhysProp
    water solubilitySlightly solubleNot Available
    logP1.84HANSCH,C ET AL. (1995)
    pKa7.8Not Available
    Predicted Properties
    PropertyValueSource
    water solubility7.10e-01 g/lALOGPS
    logP1.95ALOGPS
    logP1.63ChemAxon
    logS-2.5ALOGPS
    pKa (strongest acidic)8.4ChemAxon
    physiological charge0ChemAxon
    hydrogen acceptor count3ChemAxon
    hydrogen donor count1ChemAxon
    polar surface area66.48ChemAxon
    rotatable bond count2ChemAxon
    refractivity64.64ChemAxon
    polarizability24.62ChemAxon
    number of rings2ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterYesChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    SpectraNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    External Links
    ResourceLink
    KEGG DrugD00700
    KEGG CompoundC07829
    PubChem Compound8271
    PubChem Substance46505197
    ChemSpider7972
    ChEBI6758
    ChEMBL
    Therapeutic Targets DatabaseDAP000680
    PharmGKBPA450374
    RxListhttp://www.rxlist.com/cgi/generic2/mephobarbital.htm
    WikipediaMephobarbital
    ATC CodesN03AA01
    AHFS CodesNot Available
    PDB EntriesNot Available
    FDA labelNot Available
    MSDSNot Available
    Interactions
    Drug Interactions
    Drug
    AminophyllineThe barbiturate, methylphenobarbital, decreases the effect of aminophylline.
    BetamethasoneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, betamethasone.
    ClomifeneThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, clomifene.
    Conjugated EstrogensThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, conjugated estrogens.
    CyclosporineThe barbiturate, methylphenobarbital, increases the effect of cyclosporine.
    DelavirdineThe anticonvulsant, methylphenobarbital, decreases the effect of delavirdine.
    DexamethasoneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, dexamethasone.
    DiethylstilbestrolThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
    DoxycyclineThe anticonvulsant, methylphenobarbital, decreases the effect of doxycycline.
    EstradiolThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, estradiol.
    Ethinyl EstradiolThis product may cause a slight decrease of contraceptive effect
    FelodipineThe barbiturate, methylphenobarbital, decreases the effect of felodipine.
    FludrocortisoneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, fludrocortisone.
    Folic AcidFolic acid decreases the effect of anticonvulsant, methylphenobarbital.
    GefitinibThe CYP3A4 inducer, methylphenobarbital, may decrease the serum concentration and therapeutic effects of gefitinib.
    GriseofulvinThe barbiturate, methylphenobarbital, decreases the effect of griseofulvin.
    HydrocortisoneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, hydrocortisone.
    LevonorgestrelPhenobarbital decreases the effect of levonorgestrel
    Medroxyprogesterone AcetateThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
    Megestrol acetateThe enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, megestrol.
    MethadoneThe barbiturate, methylphenobarbital, decreases the effect of methadone.
    MetronidazoleThe barbiturate, methylphenobarbital, decreases the effect of metronidazole.
    NifedipineThe barbiturate, methylphenobarbital, decreases the effect of the calcium channel blocker, nifedipine.
    NorethindroneThis product may cause a slight decrease of contraceptive effect
    OxtriphyllineThe barbiturate, methylphenobarbital, decreases the effect of oxtriphylline.
    PrednisoloneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, prednisolone.
    PrednisoneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, prednisone.
    QuinidineThe anticonvulsant, methylphenobarbital, decreases the effect of quinidine.
    TheophyllineThe barbiturate, methylphenobarbital, decreases the effect of theophylline.
    TriamcinoloneThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, triamcinolone.
    VerapamilMethylphenobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Methylphenobarbital is initiated, discontinued or dose changed.
    Food InteractionsNot Available

    1. Gamma-aminobutyric acid receptor subunit alpha-1

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details

    References:

    1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. Pubmed
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    3. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
    6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
    7. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
    8. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed
    9. Roden WH, Peugh LD, Jansen LA: Altered GABA receptor subunit expression and pharmacology in human Angelman syndrome cortex. Neurosci Lett. 2010 Oct 15;483(3):167-72. Epub 2010 Aug 6. Pubmed

    2. Gamma-aminobutyric acid receptor subunit alpha-2

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    3. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed

    3. Gamma-aminobutyric acid receptor subunit alpha-3

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    3. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed

    4. Gamma-aminobutyric acid receptor subunit alpha-4

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details

    References:

    1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    2. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed

    5. Gamma-aminobutyric acid receptor subunit alpha-5

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    3. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed

    6. Gamma-aminobutyric acid receptor subunit alpha-6

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: potentiator

    Components

    Name UniProt ID Details
    Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details

    References:

    1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
    2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    3. Olsen RW, Li GD: GABA receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2010 Dec 31. Pubmed

    7. Neuronal acetylcholine receptor subunit alpha-4

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Neuronal acetylcholine receptor subunit alpha-4 P43681 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. Pubmed
    3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

    8. Neuronal acetylcholine receptor subunit alpha-7

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Neuronal acetylcholine receptor subunit alpha-7 P36544 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. Pubmed
    3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

    9. Glutamate receptor 2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Glutamate receptor 2 P42262 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

    10. Glutamate receptor ionotropic, kainate 2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Glutamate receptor ionotropic, kainate 2 Q13002 Details

    References:

    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
    2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

    1. Cytochrome P450 2C19

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 2C19 P33261 Details

    References:

    1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
    2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    2. Cytochrome P450 2B6

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 2B6 P20813 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    Comments
    Drug created on June 13, 2005 07:24 / Updated on October 23, 2013 09:14