Banner
targets (10) enzymes (2)
for drugs
Identification
Name Methylphenobarbital
Accession Number DB00849 (APRD00047)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Mephobarbital
Mephobarbitone
Methyl Phenobarbitone
Methylphenobarbitalum [INN-Latin]
Methylphenobarbitonum
Methylphenolbarbital
Methylphenylbarbituric acid
Metilfenobarbital [INN-Spanish]
Metilfenobarbitale [Dcit]
N-Ethylmethylphenylbarbituric acid
N-Methylethylphenylbarbituric acid
N-Methylphenobarbital
N-Methylphenolbarbitol
First Prev Next Last
Salts Not Available
Brand names
Name Company
Enfenemal
Enphenemal
Enphenemalum
Mebaral
Meberal
Mebroin
Menta-Bal
Mephytal
Methyl-Calminal
Metylfenemal
Metyna
Morbusan
Phemetone
Phemiton
Phemitone
Phenmiton
Prominal
First Prev Next Last
Brand mixtures Not Available
Categories
  • Hypnotics and Sedatives
  • Anticonvulsants
  • GABA Modulators
CAS number 115-38-8
Weight Average: 246.2619
Monoisotopic: 246.100442324
Chemical Formula C13H14N2O3
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec show (8.57 KB)
Taxonomy
Kingdom Organic
Classes
  • Barbiturates
  • Phenethylamines
Substructures
  • Barbiturates
  • Carbonyl Compounds
  • Carboxylic Acids and Derivatives
  • Amino Ketones
  • Benzene and Derivatives
  • Ureas and Derivatives
  • Pyrimidines and Derivatives
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
Pharmacology
Indication For the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy.
Pharmacodynamics Methylphenobarbital, 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 action Methylphenobarbital 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.
Absorption Approximately 50% of an oral dose of mephobarbital is absorbed from the gastrointestinal tract.
Volume of distribution Not Available
Protein binding 70-76%
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.
Route of elimination Not Available
Half life 34 (range 11-67) hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Mentax 1% cream 4.0 USD g
Mebaral 100 mg tablet 1.73 USD tablet
Mebaral 50 mg tablet 1.28 USD tablet
Mebaral 32 mg tablet 0.87 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 176 °C PhysProp
water solubility Slightly soluble Not Available
logP 1.84 HANSCH,C ET AL. (1995)
pKa 7.8 Not Available
Predicted Properties
Property Value Source
water solubility 7.10e-01 g/l ALOGPS
logP 1.95 ALOGPS
logP 1.63 ChemAxon
logS -2.5 ALOGPS
pKa (strongest acidic) 8.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 66.48 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 64.64 ChemAxon
polarizability 24.62 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00700 Link_out
KEGG Compound C07829 Link_out
PubChem Compound 8271 Link_out
PubChem Substance 46505197 Link_out
ChemSpider 7972 Link_out
ChEBI 6758 Link_out
ChEMBL 6758 Link_out
Therapeutic Targets Database DAP000680 Link_out
PharmGKB PA450374 Link_out
RxList http://www.rxlist.com/cgi/generic2/mephobarbital.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Mephobarbital Link_out
ATC Codes
  • N03AA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Aminophylline The barbiturate, methylphenobarbital, decreases the effect of aminophylline.
Betamethasone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, betamethasone.
Clomifene The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, clomifene.
Conjugated Estrogens The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, conjugated estrogens.
Cyclosporine The barbiturate, methylphenobarbital, increases the effect of cyclosporine.
Delavirdine The anticonvulsant, methylphenobarbital, decreases the effect of delavirdine.
Dexamethasone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, dexamethasone.
Diethylstilbestrol The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Doxycycline The anticonvulsant, methylphenobarbital, decreases the effect of doxycycline.
Estradiol The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, estradiol.
Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
Felodipine The barbiturate, methylphenobarbital, decreases the effect of felodipine.
Fludrocortisone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, fludrocortisone.
Folic Acid Folic acid decreases the effect of anticonvulsant, methylphenobarbital.
Gefitinib The CYP3A4 inducer, methylphenobarbital, may decrease the serum concentration and therapeutic effects of gefitinib.
Griseofulvin The barbiturate, methylphenobarbital, decreases the effect of griseofulvin.
Hydrocortisone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, hydrocortisone.
Levonorgestrel Phenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, megestrol.
Methadone The barbiturate, methylphenobarbital, decreases the effect of methadone.
Metronidazole The barbiturate, methylphenobarbital, decreases the effect of metronidazole.
Nifedipine The barbiturate, methylphenobarbital, decreases the effect of the calcium channel blocker, nifedipine.
Norethindrone This product may cause a slight decrease of contraceptive effect
Oxtriphylline The barbiturate, methylphenobarbital, decreases the effect of oxtriphylline.
Prednisolone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, prednisolone.
Prednisone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, prednisone.
Quinidine The anticonvulsant, methylphenobarbital, decreases the effect of quinidine.
Theophylline The barbiturate, methylphenobarbital, decreases the effect of theophylline.
Triamcinolone The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, triamcinolone.
Verapamil Methylphenobarbital, 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 Interactions Not Available
Targets

1. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P14867 Link_out
Gene: GABRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P47869 Link_out
Gene: GABRA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P34903 Link_out
Gene: GABRA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P48169 Link_out
Gene: GABRA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P31644 Link_out
Gene: GABRA5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: potentiator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: Q16445 Link_out
Gene: GABRA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: P43681 Link_out
Gene: CHRNA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: P36544 Link_out
Gene: CHRNA7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

Receptor for glutamate. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. This receptor binds AMPA(quisqualate) > glutamate > kainate

Organism class: human
UniProt ID: P42262 Link_out
Gene: GRIA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. May be involved in the transmission of light information from the retina to the hypothalamus. This receptor binds domoate > kainate > quisqualate > 6-cyano-7-nitroquinoxaline-2,3-dione > L-glutamate = 6,7- dinitroquinoxaline-2,3-dione > dihydrokainate

Organism class: human
UniProt ID: Q13002 Link_out
Gene: GRIK2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. Cytochrome P450 2C19

Actions: substrate, inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20813 Link_out
Gene: CYP2B6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19