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Metharbital

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1 FDF Dossiers
1 FDA Orange Book

Synopsis

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Chemistry

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Also known as: Metharbitone, Methylbarbital, Gemonil, Metabarbital, N-methylbarbital, Endiemalum

Molecular Formula

C₉H₁₄N₂O₃

Molecular Weight

198.22 g/mol

InChI Key

FWJKNZONDWOGMI-UHFFFAOYSA-N

FDA UNII

02OS7K758T

Metharbital is a barbiturate anticonvulsant, similar to phenobarbital, marketed as Gemonil by Abbott Laboratories. It was patented in 1905 by Emil Fischer of Merck.

1 2D Structure

Metharbital

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)

2.1.3 InChI Key

FWJKNZONDWOGMI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC1(C(=O)NC(=O)N(C1=O)C)CC

2.2 Other Identifiers

2.2.1 UNII

02OS7K758T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Endiemal

2. Metharbitone

3. Methobarbitone

2.3.2 Depositor-Supplied Synonyms

1. Metharbitone

2. Methylbarbital

3. Gemonil

4. Metabarbital

5. N-methylbarbital

6. Endiemalum

7. Metharbutal

8. 50-11-3

9. 1-methylbarbital

10. Endiemal

11. Gemonit

12. 5,5-diethyl-1-methylbarbituric Acid

13. 5,5-diethyl-1-methyl-1,3-diazinane-2,4,6-trione

14. Sch 412

15. An 23

16. Metharbital Ciii

17. Nsc 27156

18. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5,5-diethyl-1-methyl-

19. Barbituric Acid, 5,5-diethyl-1-methyl-

20. Methabarbital

21. Nsc-27156

22. 5,5-diethyl-1-methylpyrimidine-2,4,6(1h,3h,5h)-trione

23. Methabarbitone

24. Metarbitale [dcit]

25. 02os7k758t

26. Metharbital Ciii (200 Mg)

27. Metarbital [inn-spanish]

28. Ncgc00181148-01

29. Metarbitale

30. Metharbitalum

31. Metarbital

32. Metharbitalum [inn-latin]

33. Gemonil (tn)

34. Metharbital (jan/inn)

35. Einecs 200-011-2

36. Brn 0184688

37. Unii-02os7k758t

38. 5,5-diethyl-1-methyl-2,4,6(1h,3h,5h)-pyrimidinetrione

39. Metharbital [usp:inn:ban:jan]

40. Metharbital [mi]

41. Metharbital [inn]

42. Metharbital [jan]

43. Dsstox_cid_3280

44. Chembl450

45. Metharbital [vandf]

46. Dsstox_rid_76955

47. Metharbital [mart.]

48. Dsstox_gsid_23280

49. Schembl78867

50. Metharbital [who-dd]

51. 5-24-09-00144 (beilstein Handbook Reference)

52. Gtpl7230

53. Dtxsid6023280

54. Schembl22556220

55. Chebi:31827

56. Metharbital [orange Book]

57. Metharbital 1.0 Mg/ml In Methanol

58. Nsc27156

59. Zinc5508997

60. Tox21_112752

61. Barbituric Acid,5-diethyl-1-methyl-

62. 1-methyl-5,5-diethyl Barbituric Acid

63. Akos006239548

64. Wln: T6vmvnv Fhj D1 F2 F2

65. Db00463

66. Cas-50-11-3

67. Ft-0692647

68. 5,5-diethyl-1-methyl-barbituric-acid

69. D01382

70. Q1176294

71. 5,5-diethyl-1-methyl-2,4,6-trioxo-hexahydropyrimidine

72. Z2205958937

73. 2,6(1h,3h,5h)-pyrimidinetrione, 5,5-diethyl-1-methyl-

74. 5,5-diethyl-1-methyl-2,4,6(1h,3h,5h)-pyrimidinetrione #

75. 5,5-diethyl-6-hydroxy-3-methyl-2,3,4,5-tetrahydropyrimidine-2,4-dione

76. Vok

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₄N₂O₃
Molecular Weight	198.22 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	198.10044231 g/mol
Monoisotopic Mass	198.10044231 g/mol
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	294
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Metharbital is used for the treatment of epilepsy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Metharbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.

5.2 ATC Code

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AA - Barbiturates and derivatives

N03AA30 - Metharbital

5.3 Mechanism of Action

Metharbital binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A 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.