MEPHOBARBITAL

MEPHOBARBITAL Basic information
Product Name:MEPHOBARBITAL
Synonyms:METHYLPHENOBARBITAL;MEPHOBARBITAL;1-Methyl-5-ethyl-5-phenylbarbituric acid;1-methyl-5-ethyl-5-phenylbarbituricacid;1-Methyl-5-ethyl-5-phenyl-pyrimidine-2,4,6-trione;1-Methyl-5-phenyl-5-ethylbarbituric acid;1-methyl-5-phenyl-5-ethylbarbituricacid;1-Methylphenobarbital
CAS:115-38-8
MF:C13H14N2O3
MW:246.26
EINECS:204-085-7
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:115-38-8.mol
MEPHOBARBITAL Structure
MEPHOBARBITAL Chemical Properties
Melting point 1760C
Boiling point 389.26°C (rough estimate)
density 1.1855 (rough estimate)
refractive index 1.6450 (estimate)
Fp 11 °C
storage temp. Controlled Substance, -20°C Freezer
solubility Practically insoluble in water, very slightly soluble in ethanol (96 per cent).
pka7.99±0.10(Predicted)
form Solid
color White to Off-White
Water Solubility 0.15g/L(20 ºC)
CAS DataBase Reference115-38-8
EPA Substance Registry System2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl- (115-38-8)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 22-39/23/24/25-23/24/25-11
Safety Statements 36/37/39-45-36/37-16-7
RIDADR 3249
HazardClass 6.1(b)
PackingGroup III
HS Code 2933530000
Hazardous Substances Data115-38-8(Hazardous Substances Data)
Toxicitycat,LD50,oral,230mg/kg (230mg/kg),Drugs in Japan Vol. 6, Pg. 851, 1982.
MSDS Information
MEPHOBARBITAL Usage And Synthesis
Chemical PropertiesWhite Crystalline Solid
OriginatorIsonal, Roussel
UsesControlled substance (depressant). Anticonvulsant; sedative; hypnotic
DefinitionChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by ethyl and phenyl groups.
Manufacturing Process46 parts metallic sodium was dissolved in 1000 parts absolute alcohol. The obtained solution was mixed with 264 parts of phenyl ethyl malonic acid diethyl ester and 80 parts of monomethyl urea and heated for 8 hours at reflux. Alcohol was distilled off, the residue was dissolved in water and neutralized with diluted sulfuric acid. N-Methylethylphenylbarbituric acid precipitated as a powder. It was filtered off, washed to neutral and dissolved in 50 parts of boiling alcohol. On cooling the obtained methylphenobarbital precipitated as the colorless prisms. MP: 176.5°C. This compound may be also prepared by condensation of equivalents of phenyl malonic ester and monomethyl urea, which was dissolved in above described solution of sodium ethylate.
Brand nameMebaral (Sterling Winthrop); Menta-Bal (Marion Merrell Dow).
Therapeutic FunctionAnticonvulsant
General DescriptionMephobarbital, 3-methyl-5-ethyl-5-phenylbarbituric acid (metharbital), is metabolicallyN-demethylated to phenobarbital, which many consider toaccount for almost all of the activity. Its principal use is asan anticonvulsant.
Clinical UseMephobarbital is a barbiturate-derivative AED with a pKa of 7.7 (log P = 1.84 at pH 7.4). Approximately 50% of an oral dose of mephobarbital is absorbed from the gastrointestinal tract. The plasma concentrations required for its therapeutic effects are unknown. The principal route of mephobarbital metabolism is N-demethylation by the liver to form phenobarbital, which may be excreted in the urine unchanged and as its p-hydroxy metabolite and glucuronide or sulfate conjugates. Conversion to the 4-hydroxy metabolite is stereoselective, being catalyzed by either CYP2C19 (R-enantiomer) or CYP2B6 (S-enantiomer); individuals who are CYP2C19 poor metabolizers show decreased clearance. Approximately 75% of a single oral dose of mephobarbital is converted to phenobarbital. It has not been determined whether mephobarbital contributes to the antiseizure effect or whether it results from its active metabolite, phenobarbital. Similarly, it is unclear whether mephobarbital, like phenobarbital, is a potent inducer of the enzymes involved in the metabolism of other drugs, but because the drug is chemically and pharmacologically similar to phenobarbital and is metabolized to phenobarbital, this possibility is likely.
Mephobarbital is less commonly used in the treatment of generalized and partial seizures. Like phenobarbital, it is classified as a long-acting barbiturate. No evidence exists that it is more effective than phenobarbital in equivalent doses; however, it may be less sedating in children.
Safety ProfilePoison by ingestion and intraperitoneal routes. A human teratogen by an unspecified route with developmental abnormalities of the cardovascular (circulatory) system. When heated to decomposition it emits toxic NOx. See also BARBITURATES.
MEPHOBARBITAL Preparation Products And Raw materials
Raw materialsSodium-->Methylurea
Preparation Products(S)-MEPHENYTOIN
febarbamate PHENOBARBITAL-1-BUTYRIC ACID AURORA KA-4706 1,3-Bis(phenylmethyl)-5-ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrion e MEPHOBARBITAL Diphenylhydantoin and Mephobarbital(1:2) dimethylphenobarbital ADIPHENE Eterobarb 5-ETHYL-1-(2-FLUOROBENZOYL)-5-PHENYLPYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE N-Methoxymethyl Phenobarbital (S)-Mephobarbital difebarbamate IMET 176-68 5-ETHYL-1,3-BIS(2-FLUOROBENZOYL)-5-PHENYLPYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE (R)-Mephobarbital Benzobarbital MEPHOBARBITAL CONTROLLED SUBSTANCE CIV USP(CRM STANDARD)

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