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Methohexital

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Chemistry

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Also known as: Methohexitone, 151-83-7, Methodrexitone, Enallynymall, Methohexitalum, Metohexital

Molecular Formula

C₁₄H₁₈N₂O₃

Molecular Weight

262.30 g/mol

InChI Key

NZXKDOXHBHYTKP-UHFFFAOYSA-N

FDA UNII

E5B8ND5IPE

An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.

Methohexital is a Barbiturate.

1 2D Structure

Methohexital

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione

2.1.2 InChI

InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)

2.1.3 InChI Key

NZXKDOXHBHYTKP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC#CC(C)C1(C(=O)NC(=O)N(C1=O)C)CC=C

2.2 Other Identifiers

2.2.1 UNII

E5B8ND5IPE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Brevimytal Natrium

2. Brevital

3. Brietal

4. Brietal Sodium

5. Brietal-sodium

6. Methohexital Sodium

7. Methohexital, Monosodium Salt

8. Methohexitone

9. Monosodium Salt Methohexital

10. Natrium, Brevimytal

11. Sodium, Methohexital

2.3.2 Depositor-Supplied Synonyms

1. Methohexitone

2. 151-83-7

3. Methodrexitone

4. Enallynymall

5. Methohexitalum

6. Metohexital

7. Brietal

8. 5-allyl-5-(3-hexyn-2-yl)-1-methylbarbituric Acid

9. Compound 22451

10. Compound 25398

11. 18652-93-2

12. (+-)-5-allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric Acid

13. 5-hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione

14. Chebi:102216

15. 5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1h,3h,5h)-pyrimidinetrione

16. E5b8nd5ipe

17. Metoesital

18. 5-allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione

19. Enallynymalum

20. Barbituric Acid, 5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-

21. Alpha-dl-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric Acid

22. Metoesital [dcit]

23. (+/-)-5-allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric Acid

24. .alpha.-dl-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric Acid

25. Barbituric Acid, 5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-, (.+/-.)-

26. Metohexital [inn-spanish]

27. Dea No. 2264

28. Methohexitalum [inn-latin]

29. Methohexital (usp/inn)

30. Unii-e5b8nd5ipe

31. Methohexital [usp:inn:ban]

32. Methohexital Civ

33. Einecs 205-798-6

34. Methohexital [mi]

35. Methohexital [inn]

36. Epitope Id:117125

37. Chembl7413

38. Methohexital [vandf]

39. Schembl80729

40. Methohexital [mart.]

41. Methohexital [who-dd]

42. Gtpl7233

43. Dtxsid1023287

44. Methohexital Civ [usp-rs]

45. Act02624

46. Methohexital [usp Monograph]

47. Methohexital 1.0 Mg/ml In Methanol

48. 5-allyl-5-(hex-3-yn-2-yl)-1-methylpyrimidine-2,4,6(1h,3h,5h)-trione

49. Db00474

50. 1-methyl-5-(1-methylpent-2-yn-1-yl)-5-(prop-2-en-1-yl)pyrimidine-2,4,6(1h,3h,5h)-trione

51. 1-methyl-5-(1-methylpent-2-yn-1-yl)-5-prop-2-en-1-ylpyrimidine-2,4,6(1h,3h,5h)-trione

52. 2,4,6(1h,3h,5h)-pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-

53. 5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

54. 2,4,6(1h,3h,5h)-pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-, (+/-)-

55. Bm164664

56. Db-043117

57. C07844

58. D04985

59. A809228

60. Q851813

61. 1-methyl-5-(1-methyl-2-pentynyl)-5-allyl-barbituric Acid

62. Dl-1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-2,4,6(1h,3h,5h)-pyrimidinetrione

63. 2,4(3h,5h)-pyrimidinedione, 6-hydroxy-3-methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-

64. 2,4,6(1h,3h,5h)-pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-, (+-)-

65. 2,4,6(1h,3h,5h)-pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-, (.+/-.)-

66. 5-(hex-3-yn-2-yl)-6-hydroxy-3-methyl-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydropyrimidine-2,4-dione

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₈N₂O₃
Molecular Weight	262.30 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	262.13174244 g/mol
Monoisotopic Mass	262.13174244 g/mol
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	497
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Methohexital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.

5.2 MeSH Pharmacological Classification

Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

METHOHEXITAL

5.3.2 FDA UNII

E5B8ND5IPE

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Barbiturates

5.4 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AF - Barbiturates, plain

N01AF01 - Methohexital

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CA - Barbiturates, plain

N05CA15 - Methohexital

5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability following rectal administration of methohexital is 17%.

Route of Elimination

Excretion occurs via the kidneys through glomerular filtration.

5.6 Metabolism/Metabolites

Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.

5.7 Biological Half-Life

5.6 ± 2.7 minutes

5.8 Mechanism of Action

Methohexital 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.

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DOSAGE - INJECTABLE;INJECTION - 2.5GM/VIAL

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DOSAGE - INJECTABLE;INJECTION - 500MG/VIAL

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