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Tox21_300271

Tox21_300271

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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

Tox21_300271

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 Formula	C₁₂H₁₁N₂NaO₃
Molecular Weight	254.22 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	254.06673650 g/mol
Monoisotopic Mass	254.06673650 g/mol
Topological Polar Surface Area	81.6 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	378
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)