mephobarbital

Also known as 1-methylphenobarbital, mephobarbitone, 5-ethyl-1-methyl-5-phenylbarbituric acid, N-methylphenobarbital, methylphenobarbitone, 5-ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trione, 5-ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

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, but also as a sedative and anxiolytic. It is the N-methylated analogue of phenobarbital and has similar indications, therapeutic value, and tolerability.

Chemical data

Formula: C13H14N2O3
Molecular weight: 246.26 g/mol
IUPAC name: 5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione
SMILES: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2
InChIKey: ALARQZQTBTVLJV-UHFFFAOYSA-N
XLogP: 1.8
Polar surface area: 66.5 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Wikidata facts

Mass: 246.100442

Show 5 more facts

defined daily dose: 0.5
chemical formula: C₁₃H₁₄N₂O₃
canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2
World Health Organisation international non-proprietary name: methylphenobarbital
Commons category: Methylphenobarbital

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Article

5 sections

Contents

Approval history
Side effects
Overdose
See also
References

== 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 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."