Methylphenobarbital

Methylphenobarbital
Methylphenobarbital
Systematic (IUPAC) name
5-phenyl-5-ethyl-
3-methylbarbituric acid
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a605022
Pregnancy cat.  ?
Legal status Schedule IV (US)
Routes  ?
Pharmacokinetic data
Bioavailability  ?
Protein binding 70-76%
Metabolism Hepatic
Half-life 34 hours
Excretion  ?
Identifiers
CAS number 115-38-8 YesY
ATC code N03AA01
PubChem CID 8271
DrugBank APRD00047
ChemSpider 7972 YesY
UNII 5NC67NU76B YesY
KEGG D00700 YesY
ChEBI CHEBI:6758 N
ChEMBL CHEMBL45029 YesY
Chemical data
Formula C13H14N2O3 
Mol. mass 246.3
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Methylphenobarbital, also known as mephobarbital, (marketed in the US under the brand name Mebaral by Lundbeck) is a drug which is a barbiturate derivative.

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

Contents

Approval History

  • 1935 Mebaral was introduced by Winthrop Pharmaceuticals.
  • 2001 Methylphenobarbital discontinued in the UK.
  • 2003 Mebaral acquired by Ovation Pharmaceuticals (a specialty pharmaceutical company that acquired underpromoted branded pharmaceutical products).
  • 2009 Ovation was acquired by Lundbeck, which now markets Mebaral. However, Lundbeck recently announced that they are abandoning the product because, under the FDA unapproved-drug campaign, FDA is no longer willing to allow it to be grandfathered. A new drug application was never submitted to the FDA to gain marketing approval. The drug will no longer be available when supplies are depleted, which is anticipated by the end of 2011.

Overdose symptoms

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

Chemistry

Mephobarbital (5-ethyl-1-methyl-5-phenylbarbituric acid) is synthesized according to one of the diagrams used for the phenobarbital synthesis, except one uses methylurea instead.

References

  • The Treatment of Epilepsy 2nd Ed by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
v · d · eAnticonvulsants (N03)
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#WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III

M: CNS

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