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    5-Ethyl-5-phenylbarbituric acid sodium salt

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    2D Structure
    Also known as: 57-30-7, Phenobarbital sodium salt, Sodium phenobarbital, Sodium phenobarbitone, Luminal sodium, Sodium luminal
    Molecular Formula
    C12H11N2NaO3
    Molecular Weight
    254.22  g/mol
    InChI Key
    WRLGYAWRGXKSKG-UHFFFAOYSA-M
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;5-ethyl-4,6-dioxo-5-phenyl-1H-pyrimidin-2-olate
    2.1.2 InChI
    InChI=1S/C12H12N2O3.Na/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16;/h3-7H,2H2,1H3,(H2,13,14,15,16,17);/q;+1/p-1
    2.1.3 InChI Key
    WRLGYAWRGXKSKG-UHFFFAOYSA-M
    2.1.4 Canonical SMILES
    CCC1(C(=O)NC(=NC1=O)[O-])C2=CC=CC=C2.[Na+]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Acid, Phenylethylbarbituric

    2. Gardenal

    3. Hysteps

    4. Luminal

    5. Monosodium Salt Phenobarbital

    6. Phenemal

    7. Phenobarbital

    8. Phenobarbital, Monosodium Salt

    9. Phenobarbitone

    10. Phenylbarbital

    11. Phenylethylbarbituric Acid

    12. Sodium, Phenobarbital

    2.2.2 Depositor-Supplied Synonyms

    1. 57-30-7

    2. Phenobarbital Sodium Salt

    3. Sodium Phenobarbital

    4. Sodium Phenobarbitone

    5. Luminal Sodium

    6. Sodium Luminal

    7. Sodium Phenobarbiturate

    8. Phenobarbital Sodique

    9. Sodium Phenylethylbarbiturate

    10. Sodium Phenylethylmalonylurea

    11. Sodium 5-ethyl-5-phenylbarbiturate

    12. Phenobarbital, Sodium

    13. Phenobarbitalum Natricum

    14. Sodium 5-ethyl-4,6-dioxo-5-phenyl-1,4,5,6-tetrahydropyrimidin-2-olate

    15. 5-ethyl-5-phenylbarbituric Acid Sodium Salt

    16. Phenyl-aethyl-barbitursaeure Natrium

    17. Sodium 5-ethyl-4,6-dioxo-5-phenyl-1h-pyrimidin-2-olate

    18. Phenobarbitone Sodium

    19. Phenemalnatrium

    20. Phenobal Sodium

    21. Phenobarbital Na

    22. Sol Phenobarbital

    23. Sol Phenobarbitone

    24. Phenobarbitalnatrium

    25. Phenobarbital Elixir

    26. Phenobarbiton-natrium

    27. Soluble Phenobarbital

    28. Soluble Phenobarbitone

    29. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-ethyl-5-phenyl-, Monosodium Salt

    30. Sodium;5-ethyl-4,6-dioxo-5-phenyl-1h-pyrimidin-2-olate

    31. Sw9m9bb5k3

    32. Phenobarbitone Sodium Salt

    33. Chebi:8070

    34. Fenobarbital Sodico

    35. Fenobarbital Natrium

    36. Ccris 503

    37. Fenobarbital Natrium [polish]

    38. Fenobarbital Sodico [inn-spanish]

    39. Phenobarbital Sodique [inn-french]

    40. Einecs 200-322-3

    41. Phenobarbitalum Natricum [inn-latin]

    42. Unii-sw9m9bb5k3

    43. Phenylethylbarbituric Acid, Sodium Salt

    44. Phenyl-aethyl-barbitursaeure Natrium [german]

    45. Phenobarbital Sodium [usp:inn:jan]

    46. Luminal Sodium (tn)

    47. 5-ethyl-5-phenyl-2,4,6-(1h,3h,5h)pyrimidinetrione Monosodium Salt

    48. Dsstox_cid_1123

    49. Dsstox_rid_75954

    50. Barbituric Acid, 5-ethyl-5-phenyl-, Sodium Salt

    51. Dsstox_gsid_21123

    52. Schembl42037

    53. Dtxsid0021123

    54. Tox21_300271

    55. Phenobarbital Sodium (jan/usp/inn)

    56. Akos015960550

    57. Cas-57-30-7

    58. Ncgc00253999-01

    59. Ac-11674

    60. Db-053032

    61. P0890

    62. D00701

    63. A831383

    64. W-105476

    65. Q26840934

    66. Sodium;5-ethyl-5-phenylpyrimidin-3-ide-2,4,6-trione

    67. 5-ethyl-5-phenyl-2,4,6(1h,3h,5h)-pyrimidinetrione Sodium Salt

    68. Sodium 5-ethyl-4,6-bis(oxidanylidene)-5-phenyl-1h-pyrimidin-2-olate

    2.3 Create Date
    2008-02-05
    3 Chemical and Physical Properties
    Molecular Weight 254.22 g/mol
    Molecular Formula C12H11N2NaO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass254.06673650 g/mol
    Monoisotopic Mass254.06673650 g/mol
    Topological Polar Surface Area81.6 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity378
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Cytochrome P-450 CYP2B6 Inducers

    Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP2B6. (See all compounds classified as Cytochrome P-450 CYP2B6 Inducers.)

    Cytochrome P-450 CYP3A Inducers

    Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inducers.)

    Excitatory Amino Acid Antagonists

    Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists. (See all compounds classified as Excitatory Amino Acid Antagonists.)

    GABA Modulators

    Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

    Hypnotics and Sedatives

    Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)