Classification Term: 623

Barbituric acid derivatives (ontology term: CHEMONTID:0000292)

Compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups." []

found 35 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Pyrimidones

Child Taxonomies: There is no child term of current ontology term.

Methohexital

5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

C14H18N2O3 (262.1317)


Methohexital is only found in individuals that have used or taken this drug. It is an intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]Methohexital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain N - Nervous system > N01 - Anesthetics > N01A - Anesthetics, general > N01AF - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Aprobarbital

5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

C10H14N2O3 (210.1004)


Aprobarbital is a barbiturate derivative synthesized in the 1920s by Ernst Preiswerk. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia. Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed. N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Butabarbital

2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, monosodium salt

C10H16N2O3 (212.1161)


Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia] D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Phenobarbital

5-Ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione

C12H12N2O3 (232.0848)


Phenobarbital is only found in individuals that have used or taken this drug. It is a barbituric acid derivative that acts as a nonselective central nervous system depressant.Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal. Phenobarbital appears as odorless white crystalline powder or colorless crystals. A saturated aqueous solution is acid to litmus (approximately pH 5). Slightly bitter taste. (NTP, 1992) Phenobarbital is a member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups. It has a role as an anticonvulsant, a sedative, an excitatory amino acid antagonist and a drug allergen. Phenobarbital is a DEA Schedule IV controlled substance. Substances in the DEA Schedule IV have a low potential for abuse relative to substances in Schedule III. It is a Depressants substance. A barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. Phenobarbital is a barbiturate that is widely used as a sedative and an antiseizure medication. Phenobarbital has been linked to rare instances of idiosyncratic liver injury that can be severe and even fatal. Phenobarbital is a long-acting barbituric acid derivative with antipsychotic property. Phenobarbital binds to and activates the gamma-aminobutyric acid (GABA)-A receptor, thereby mimicking the inhibitory actions of GABA in the brain. The activation effects of the phenobarbital-receptor-ionophore complex include increased frequency of chloride channel openings, membrane hyperpolarization and ultimately synaptic inhibition and decreased neuronal excitability. In addition, this agent inhibits glutamate induced depolarization. Phenobarbital is only found in individuals that have used or taken this drug. It is a barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem] Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal. A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.

   

Methylphenobarbital

5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

C13H14N2O3 (246.1004)


Methylphenobarbital is only found in individuals that have used or taken this drug. It is 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]Methylphenobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics > N03AA - Barbiturates and derivatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators D002491 - Central Nervous System Agents > D000927 - Anticonvulsants

   

Heptabarbital

5-(cyclohept-1-en-1-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

C13H18N2O3 (250.1317)


Heptabarbital is only found in individuals that have used or taken this drug. It is an intermediate or short term barbiturate used mainly for sedation and hypnosis.Heptabarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Heptabarbital also appears to bind neuronal nicotinic acetylcholine receptors. N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Bromelains

Sodium 5-ethyl-6-hydroxy-2-oxo-5-(pentan-2-yl)-2,5-dihydropyrimidin-4-olic acid

C11H17N2NaO3 (248.1137)


Enzymes occurring in pineapple juice (Ananas sativus); used in tenderising meat and chill-proofing beer [DFC]. Along with papain, bromelain is one of the most popular substances to use for meat tenderizing.; Bromelain can refer to one of two protease enzymes extracted from the plant family Bromeliaceae, or it can refer to a combination of those enzymes along with other compounds produced in an extract. [BioSpider]. Bromelains is found in pineapple and fruits. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives Enzymes occurring in pineapple juice (Ananas sativus); used in tenderising meat and chill-proofing beer [DFC] C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators

   

Secobarbital

5-(1-Methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

C12H18N2O3 (238.1317)


Secobarbital is only found in individuals that have used or taken this drug. It is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone. Secobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators

   

Butalbital

5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C11H16N2O3 (224.1161)


Butalbital, 5-allyl-5-isobutylbarbituric acid, is a barbiturate with an intermediate duration of action. It has the same chemical formula as talbutal but a different structure. Butalbital is often combined with other medications, such as acetaminophen or aspirin, and is commonly prescribed for the treatment of pain and headache. [Wikipedia] C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Metharbital

5,5-diethyl-1-methyl-1,3-diazinane-2,4,6-trione

C9H14N2O3 (198.1004)


Metharbital is only found in individuals that have used or taken this drug. It was patented in 1905 by Emil Fischer working for Merck. It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy. It has similar properties to phenobarbital. Metharbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission. N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics > N03AA - Barbiturates and derivatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

3'-Hydroxyhexobarbital

5-(3-hydroxycyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

C12H16N2O4 (252.111)


3-Hydroxyhexobarbital is only found in individuals that have used or taken Hexobarbital. 3-Hydroxyhexobarbital is a metabolite of Hexobarbital. 3-hydroxyhexobarbital belongs to the family of Barbituric Acid Derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

   

Epoxy-hexobarbital

1,5-dimethyl-5-{7-oxabicyclo[4.1.0]heptan-1-yl}-1,3-diazinane-2,4,6-trione

C12H16N2O4 (252.111)


Epoxy-hexobarbital is only found in individuals that have used or taken Hexobarbital. Epoxy-hexobarbital is a metabolite of Hexobarbital. Epoxy-hexobarbital belongs to the family of Barbituric Acid Derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

   

Talbutal

5-(butan-2-yl)-1,3-dimethyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C13H20N2O3 (252.1474)


Talbutal is only found in individuals that have used or taken this drug. It is a barbiturate with a short to intermediate duration of action. Talbutal is a schedule III drug in the U.S.Talbutal binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

   

Butethal

5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione

C10H16N2O3 (212.1161)


Butethal is only found in individuals that have used or taken this drug. It is a sedative and a hypnotic drug.Butethal binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Thymine glycol

5,6-Dihydroxy-5-methyldihydropyrimidine-2,4(1H,3H)-dione

C5H8N2O4 (160.0484)


Thymine glycol belongs to the family of Hydropyrimidines. These are compounds containing an hydrogenated pyrimidine ring (i.e containing less than the maximum bumber of double bonds.).

   

p-Hydroxyphenobarbital

2,4,6(1H,3H,5H)-Pyrimidinetrione,5-ethyl-5-(4-hydroxyphenyl)-

C12H12N2O4 (248.0797)


p-Hydroxyphenobarbital is a metabolite of Phenobarbital. Phenobarbital (INN) is a barbiturate and the most widely used anticonvulsant worldwide, and the oldest still commonly used. It also has sedative and hypnotic properties. (Wikipedia)

   

1,5-Dimethylbarbituric acid

1,5-dimethyl-1,3-diazinane-2,4,6-trione

C6H8N2O3 (156.0535)


   

3'-Hydroxyamobarbital

5-ethyl-5-(3-hydroxy-3-methylbutyl)-1,3-diazinane-2,4,6-trione

C11H18N2O4 (242.1267)


   

2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(3-hydroxy-1-methylbutyl)-

5-ethyl-5-(4-hydroxypentan-2-yl)-1,3-diazinane-2,4,6-trione

C11H18N2O4 (242.1267)


   

4'-Hydroxymethohexital

5-(5-hydroxyhex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C14H18N2O4 (278.1267)


   

5-Butyl-5-cycloheptenylbarbituric acid

5-butyl-5-(cyclooct-1-en-1-yl)-1,3-diazinane-2,4,6-trione

C16H24N2O3 (292.1787)


   

5-Ethyl-5-p-tolylbarbituric acid

5-ethyl-5-(4-methylphenyl)-1,3-diazinane-2,4,6-trione

C13H14N2O3 (246.1004)


   

Aethallymal

2,4,6(1H,3H,5H)-Pyrimidinetrione,5-ethyl-5-(2-propen-1-yl)-

C9H12N2O3 (196.0848)


N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain

   

Allobarbital

4,6-dihydroxy-5,5-bis(prop-2-en-1-yl)-2,5-dihydropyrimidin-2-one

C10H12N2O3 (208.0848)


N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

5-(Cycloocten-1-yl)-5-ethyl-barbituric acid

5-(cyclooct-1-en-1-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

C14H20N2O3 (264.1474)


   

Barbital

5,5-Diethylpyrimidine-2,4,6(1H,3H,5H)-trione

C8H12N2O3 (184.0848)


D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators

   

Cyclobarbital

5-(cyclohex-1-en-1-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

C12H16N2O3 (236.1161)


N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives > N05CA - Barbiturates, plain C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic

   

Cyclopentobarbital

5-(cyclopent-2-en-1-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C12H14N2O3 (234.1004)


C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Dialuric acid

5-hydroxy-1,3-diazinane-2,4,6-trione

C4H4N2O4 (144.0171)


   

Enallylpropymal

6-hydroxy-3-methyl-5-(prop-2-en-1-yl)-5-(propan-2-yl)-2,3,4,5-tetrahydropyrimidine-2,4-dione

C11H16N2O3 (224.1161)


   

Eterobarb

5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione

C16H20N2O5 (320.1372)


C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C67084 - Barbiturate

   

Febarbamate

{[1-butoxy-3-(5-ethyl-4-hydroxy-2,6-dioxo-5-phenyl-1,2,5,6-tetrahydropyrimidin-1-yl)propan-2-yl]oxy}carboximidic acid

C20H27N3O6 (405.19)


M - Musculo-skeletal system > M03 - Muscle relaxants > M03B - Muscle relaxants, centrally acting agents > M03BA - Carbamic acid esters C78272 - Agent Affecting Nervous System > C264 - Anticonvulsant Agent

   

N,N-Diallylpentobarbital

5-ethyl-5-(3-methylbutyl)-1,3-bis(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C17H26N2O3 (306.1943)


   

N,N'-Diallylpentobarbital

5-ethyl-5-(pentan-2-yl)-1,3-bis(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

C17H26N2O3 (306.1943)


   

VINBARBITAL

5-ethyl-5-(pent-2-en-2-yl)-1,3-diazinane-2,4,6-trione

C11H16N2O3 (224.1161)