5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 727
• Molecular Formular: C13H14N2O3
• Molecular Mass: 246.26186
• Monoisotopic Mass: 246.10044232
• SMILES: O=C1N(C(=O)NC(=O)C1(CC)c1ccccc1)C
• Canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)C)c1ccccc1
• 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)
• InChIKey: ALARQZQTBTVLJV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: methylphenobarbital; mephobarbital; 5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione
• Brand Name: Enfenemal; Enphenemal; Enphenemalum; Isonal; Mebaral; Meberal; Mebroin; Menta-Bal; Mephytal; Methyl-Calminal; Metylfenemal; Metyna; Morbusan; Phemetone; Phemiton; Phemitone; Phenmiton; Prominal
• Synonyms: 5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Ethyl-1-methyl-5-phenylbarbituric Acid; 5-Phenyl-5-ethyl-3-methylbarbituric Acid; Mebaral; Phemiton; Prominal; Mephobarbital; Mephobarbital; Mephobarbitone; Methyl Phenobarbitone; Methylphenobarbitalum [INN-Latin]; Methylphenobarbitonum; Methylphenolbarbital; Methylphenylbarbituric acid; Metilfenobarbital [INN-Spanish]; Metilfenobarbitale [Dcit]; N-Ethylmethylphenylbarbituric acid; N-Methylethylphenylbarbituric acid; N-Methylphenobarbital; N-Methylphenolbarbitol; Methylphenobarbital; Methylphenobarbitone; Enfenemal; Enphenemal; Mefobarbital; Mentabal; Phemitone; Methylphenobarbital

Database IDs

• CAS Number: 115-38-8
• PubChem SID: 46505197; 160964190
• PubChem CID: 8271
• CHEBI ID: 6758
• ATC CODE: N03AA01
• CHEMBL: 45029
• Chemspider ID: 7972
• DrugBank ID: DB00849
• KEGG ID: D00700
• Unique Ingredient Identifier: 5NC67NU76B
• Wikipedia Title: Methylphenobarbital
• Medline Plus: a605022

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.399005
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6294647
• LogD (pH = 7.4): 1.5890191
• Log P: 1.6300062
• Molar Refractivity: 64.643 cm^3
• Polarizability: 25.007318 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.95
• LOG S: -2.54
• Solubility (Water): 7.10e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Slightly soluble
• Apperance: White Solid
• Melting Point: 175-1770C
• Hydrophobicity(logP): 1.84 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

Pharmacology Properties

• Half Life: 34 hours
• Metabolism: Hepatic
• Protein Bound: 70-76%
• Legal Status: Class B (UK); Schedule IV (US)
• Mechanism of Action: Binds brain tissue protein; Binds plasma-protein; Dose-dependent respiratory depressant; Produces all levels of CNS mood alteration

Product Information

• Application(s): Analgesic; Anticonvulsant; Antispasmodic; Sedative

DETAILS

DrugBank - DB00849

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, primarily by the hepatic microsomal enzyme system. About 75% of a single oral dose of mephobarbital is metabolized to phenobarbital in 24 hours.
• Absorption: Approximately 50% of an oral dose of mephobarbital is absorbed from the gastrointestinal tract.
• Half Life: 34 (range 11-67) hours
• Protein Binding: 70-76%
• External Links: Wikipedia; RxList

Toronto Research Chemicals - M225020

Controlled substance (depressant). Anticonvulsant; sedative; hypnotic.

REFERENCES

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