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Aprobarbital

July 24, 2017
Common Name

Aprobarbital Description

Aprobarbital is a barbiturate derivative synthesized in the 1920s by Ernst Preiswerk. It has sedative, hypnotic and anticonvlisant 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI 5-Allyl-5-isopropylbarbituric acidChEBI 5-Allyl-5-isopropylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI 5-Isopropyl-5-allylbarbituric acidChEBI AllypropymalChEBI AlurateChEBI 5-Allyl-5-isopropylbarbitateGenerator 5-Allyl-5-isopropylbarbitic acidGenerator 5-Isopropyl-5-allylbarbitateGenerator 5-Isopropyl-5-allylbarbitic acidGenerator Aluric acidGenerator AlateGenerator Alic acidGenerator AllylpropymalMeSH AprobarbitoneMeSH Allylpropymal, monosodium saltMeSH

Chemical Formlia

C10H14N2O3 Average Molecliar Weight

210.2298 Monoisotopic Molecliar Weight

210.100442324 IUPAC Name

5-(prop-2-en-1-yl)-5-(propan-2-yl)-1,3-diazinane-2,4,6-trione Traditional Name

aprobarbital CAS Registry Number

77-02-1 SMILES

CC(C)C1(CC=C)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)

InChI Key

UORJNBVJVRLXMQ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Diazines Direct Parent

Barbituric acid derivatives Alternative Parents

  • Ureides
  • Diazinanes
  • Dicarboximides
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Barbiturate
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • barbiturates (CHEBI:2791 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point141 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.17e+00 g/LNot Available LogP1.15HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility5.17 mg/mLALOGPS logP1.24ALOGPS logP1.14ChemAxon logS-1.6ALOGPS pKa (Strongest Acidic)8.48ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area75.27 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity53.45 m3·mol-1ChemAxon Polarizability20.5 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01352

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01352

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01352 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    6221 KEGG Compound ID

    C07826 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Aprobarbital NuGOwiki Link

    HMDB15441 Metagene Link

    HMDB15441 METLIN ID

    Not Available PubChem Compound

    6464 PDB ID

    Not Available ChEBI ID

    2791

    Product: Eslicarbazepine (acetate)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in ionotropic glutamate receptor activity
    Specific function:
    Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2
    Gene Name:
    GRIK2
    Uniprot ID:
    Q13002
    Molecular weight:
    102582.5
    References
    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
    General function:
    Involved in ionotropic glutamate receptor activity
    Specific function:
    Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
    Gene Name:
    GRIA2
    Uniprot ID:
    P42262
    Molecular weight:
    98820.3
    References
    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA1
    Uniprot ID:
    P14867
    Molecular weight:
    51801.4
    References
    1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [PubMed:14579514 ]
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    3. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA2
    Uniprot ID:
    P47869
    Molecular weight:
    51325.9
    References
    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA3
    Uniprot ID:
    P34903
    Molecular weight:
    55164.1
    References
    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA4
    Uniprot ID:
    P48169
    Molecular weight:
    61622.6
    References
    1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA5
    Uniprot ID:
    P31644
    Molecular weight:
    52145.6
    References
    1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
    2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA6
    Uniprot ID:
    Q16445
    Molecular weight:
    51023.7
    References
    1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
    2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]

    PMID: 15380378

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