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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/04 04:50:43」(JST)

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Methylphenobarbital (INN), also known as mephobarbital (USAN, JAN) and mephobarbitone (BAN), marketed under brand names such as Mebaral, Mephyltaletten, Phemiton, and Prominal, is a drug which is a barbiturate derivative and is used primarily as an anticonvulsant,^[1] but also as a sedative and anxiolytic. It is the N-methylated analogue of phenobarbital and has similar indications, therapeutic value, and tolerability.

Approval history

1935 – Mebaral was introduced by Winthrop Pharmaceuticals.
2001 – Methylphenobarbital discontinued in the UK.
2003 – Mebaral was acquired by Ovation Pharmaceuticals (a specialty pharmaceutical company that acquired under-promoted branded pharmaceutical products).
2009 – Ovation was acquired by Lundbeck, which now markets Mebaral.
2012 – Lundbeck announced that they were abandoning the product in the US as of January 6, 2012. The stated reason was because "the company thoroughly evaluated all avenues for keeping MEBARAL TABLETS available to patients, but ultimately concluded that no matter what steps they [i.e. Lundbeck] took, patients would be forced to transition to a new therapy."

The company further stated in a letter on its website ^[2] that under the FDA's Unapproved Drugs Initiative, FDA is no longer willing to allow the drug to be grandfathered. A new drug application would have needed to have been submitted to gain marketing approval, which would have taken an estimated five years, during which time patients would be required to change their therapies in any case. The last available tablets bore an expiration date of March 31, 2012, and the drug will no longer be available in the US when supplies are depleted.

Overdose

Symptoms of overdose of mephobarbital include confusion, decrease in or loss of reflexes, somnolence, fever, irritability, hypothermia, poor judgment, shortness of breath or slow/troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness.

References

^ S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson, ed. (2004). The Treatment of Epilepsy (2nd ed.). Blackwell. ISBN 0-632-06046-8.
^ Letter from Lundbeck to prescribers

English Journal

Multiple propofol-binding sites in a γ-aminobutyric acid type A receptor (GABAAR) identified using a photoreactive propofol analog.

Jayakar SS1, Zhou X2, Chiara DC1, Dostalova Z2, Savechenkov PY3, Bruzik KS3, Dailey WP4, Miller KW5, Eckenhoff RG6, Cohen JB7.
The Journal of biological chemistry.J Biol Chem.2014 Oct 3;289(40):27456-68. doi: 10.1074/jbc.M114.581728. Epub 2014 Aug 1.
Propofol acts as a positive allosteric modulator of γ-aminobutyric acid type A receptors (GABAARs), an interaction necessary for its anesthetic potency in vivo as a general anesthetic. Identifying the location of propofol-binding sites is necessary to understand its mechanism of GABAAR modulation.
PMID 25086038

Identifying barbiturate binding sites in a nicotinic acetylcholine receptor with [3H]allyl m-trifluoromethyldiazirine mephobarbital, a photoreactive barbiturate.

Hamouda AK1, Stewart DS, Chiara DC, Savechenkov PY, Bruzik KS, Cohen JB.
Molecular pharmacology.Mol Pharmacol.2014 May;85(5):735-46. doi: 10.1124/mol.113.090985. Epub 2014 Feb 21.
At concentrations that produce anesthesia, many barbituric acid derivatives act as positive allosteric modulators of inhibitory GABAA receptors (GABAARs) and inhibitors of excitatory nicotinic acetylcholine receptors (nAChRs). Recent research on [(3)H]R-mTFD-MPAB ([(3)H]R-5-allyl-1-methyl-5-(m-trifl
PMID 24563544

How did phenobarbital's chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?

Bialer M1.
Epilepsia.Epilepsia.2012 Dec;53 Suppl 8:3-11. doi: 10.1111/epi.12024.
Phenobarbital has been in clinical use as an antiepileptic drug (AED) since 1912. The initial clinical success of phenobarbital and other barbiturates affected the design of subsequent AEDs (e.g., phenytoin, primidone, ethosuximide), developed between 1938 and 1962, the chemical structures of which
PMID 23205958

Related Pictures

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★リンクテーブル★

リンク元	「メホバルビタール」

「メホバルビタール」

Methylphenobarbital
Systematic (IUPAC) name
	5-phenyl-5-ethyl-; 1-methylbarbituric acid
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a605022
Pregnancy; category	?;
Legal status	UK: Class B; US: Schedule IV;
Routes of; administration	?
Pharmacokinetic data
Bioavailability	?
Protein binding	70-76%
Metabolism	Hepatic
Biological half-life	34 hours
Excretion	?
Identifiers
CAS Registry Number	115-38-8
ATC code	N03AA01
PubChem	CID: 8271
DrugBank	DB00849
ChemSpider	7972
UNII	5NC67NU76B
KEGG	D00700
ChEBI	CHEBI:6758
ChEMBL	CHEMBL45029
Chemical data
Formula	C13H14N2O3
Molecular mass	246.3 g/mol
	SMILES O=C1N(C(=O)NC(=O)C1(c2ccccc2)CC)C ;
	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) ; Key:ALARQZQTBTVLJV-UHFFFAOYSA-N ;
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　　[★]

英: mephobarbital
商: Mebaral
関: メフォバルビタール

[1] S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson, ed. (2004). The Treatment of Epilepsy (2nd ed.). Blackwell. ISBN 0-632-06046-8.

[2] Letter from Lundbeck to prescribers

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案内

Mebaral