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HomeProduct name listMEPHOBARBITAL

MEPHOBARBITAL

Synonym(s):Methylphenobarbital

  • CAS NO.:115-38-8
  • Empirical Formula: C13H14N2O3
  • Molecular Weight: 246.26
  • MDL number: MFCD00057563
  • EINECS: 204-085-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-15 10:44:01
MEPHOBARBITAL Structural

What is MEPHOBARBITAL?

Absorption

Approximately 50% of an oral dose of mephobarbital is absorbed from the gastrointestinal tract.

Chemical properties

White Crystalline Solid

Originator

Isonal, Roussel

The Uses of MEPHOBARBITAL

Controlled substance (depressant). Anticonvulsant; sedative; hypnotic

Background

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.

Indications

For the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy.

Definition

ChEBI: 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 Process

46 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 name

Mebaral (Sterling Winthrop); Menta-Bal (Marion Merrell Dow).

Therapeutic Function

Anticonvulsant

General Description

Mephobarbital, 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.

Pharmacokinetics

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.

Clinical Use

Mephobarbital 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 Profile

Poison 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.

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.

Properties of MEPHOBARBITAL

Melting point: 1760C
Boiling point: 389.26°C (rough estimate)
Density  1.1855 (rough estimate)
refractive index  1.6450 (estimate)
Flash point: 11 °C
storage temp.  Controlled Substance, -20°C Freezer
solubility  Practically insoluble in water, very slightly soluble in ethanol (96 per cent).
pka 7.99±0.10(Predicted)
form  Solid
color  White to Off-White
Water Solubility  0.15g/L(20 ºC)
CAS DataBase Reference 115-38-8
EPA Substance Registry System 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl- (115-38-8)

Safety information for MEPHOBARBITAL

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H370:Specific target organ toxicity, single exposure
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for MEPHOBARBITAL

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