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Isocarboxazid

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Also known as: 59-63-2, Isocarboxazide, Marplan, Enerzer, N'-benzyl-5-methylisoxazole-3-carbohydrazide, Isocarbonazid

Molecular Formula

C₁₂H₁₃N₃O₂

Molecular Weight

231.25 g/mol

InChI Key

XKFPYPQQHFEXRZ-UHFFFAOYSA-N

FDA UNII

34237V843T

An MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311)

Isocarboxazid is a Monoamine Oxidase Inhibitor. The mechanism of action of isocarboxazid is as a Monoamine Oxidase Inhibitor.

1 2D Structure

Isocarboxazid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

2.1.2 InChI

InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

2.1.3 InChI Key

XKFPYPQQHFEXRZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=NO1)C(=O)NNCC2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

34237V843T

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 59-63-2

2. Isocarboxazide

3. Marplan

4. Enerzer

5. N'-benzyl-5-methylisoxazole-3-carbohydrazide

6. Isocarbonazid

7. Benazide

8. Isocarbossazide

9. Isocarboxyzid

10. Marplon

11. N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

12. Isocarbossazide [dcit]

13. Maraplan

14. Isocarboxazide [inn-french]

15. Isocarboxazidum [inn-latin]

16. Ro 5-0831

17. Isocarboxazida [inn-spanish]

18. Bmih

19. Ro 5-0831/1

20. 5-methyl-3-isoxazolecarboxylic Acid 2-benzylhydrazide

21. 3-isoxazolecarboxylic Acid, 5-methyl-, 2-(phenylmethyl)hydrazide

22. N'-benzyl N-methyl-5-isoxazolecarboxylhydrazide-3

23. Nsc 169893

24. Isocarboxazid (inn)

25. Nsc-169893

26. 59-63-2 (free Base)

27. Mls003106729

28. 3-isoxazolecarboxylic Acid, 5-methyl-, 2-benzylhydrazide

29. 1-benzyl-2-(5-methyl-3-isoxazolylcarbonyl)hydrazine

30. Cas-59-63-2

31. Ncgc00016267-01

32. Isocarboxazida

33. Isocarboxazidum

34. Ro-5-0831

35. 34237v843t

36. Isocarboxazid [inn]

37. Smr001233334

38. Marplan (tn)

39. Ccris 9178

40. Sr-01000841192

41. Einecs 200-438-4

42. Brn 0201295

43. 1-benzyl-2-(5-methyl-3-isoxazolyl-carbonyl)hydrazine

44. Isocarboxazid [usp:inn:ban]

45. Unii-34237v843t

46. Isocarboxazid (icd)

47. Prestwick0_000795

48. Prestwick1_000795

49. Prestwick2_000795

50. Prestwick3_000795

51. Dsstox_cid_3171

52. Isocarboxazid [mi]

53. Dsstox_rid_76902

54. Dsstox_gsid_23171

55. Schembl49562

56. Bspbio_000930

57. 4-27-00-03999 (beilstein Handbook Reference)

58. Mls002154005

59. Isocarboxazid [mart.]

60. Isocarboxazid(200mg)

61. 5-methyl-n'-(phenylmethyl)isoxazole-3-carbohydrazide

62. Spbio_002869

63. Isocarboxazid [usp-rs]

64. Isocarboxazid [who-dd]

65. Bpbio1_001024

66. Gtpl7204

67. Zinc1587

68. Chembl1201168

69. Dtxsid4023171

70. Wln: T5noj C1 Evmm1r

71. Chebi:93635

72. Isocarboxazid (200 Mg)

73. Bdbm163692

74. Hms1570o12

75. Hms2097o12

76. Hms2230e11

77. Hms3369g18

78. Hms3714o12

79. Hms3887k05

80. Isocarboxazid [orange Book]

81. Tox21_110336

82. Nsc169893

83. Akos016003091

84. Ccg-220795

85. Db01247

86. Ncgc00016267-02

87. Ncgc00016267-03

88. Ncgc00016267-06

89. Ac-24841

90. Hy-13929

91. Ab00513923

92. Cs-0008613

93. Ft-0670438

94. 3-isoxazolecarboxylic Acid, 2-benzylhydrazide

95. D02580

96. N'-benzyl-5-methyl-3-isoxazolecarbohydrazide #

97. A914188

98. Q409595

99. Sr-01000841192-2

100. Sr-01000841192-3

101. 3-(2-benzylhydrazocarboxy)-5-methyl-isoxazole

102. 3-isoxazolecarboxylic Acid, 2-(phenylmethyl)hydrazide

103. 5-methyl-n'-(phenylmethyl)-3-isoxazolecarbohydrazide

104. Brd-k93332168-001-03-2

105. Isocarboxazid 5-methyl-3-isoxazole-carboxylic Acid 2-benzylhydrazide, Aldrichcpr

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₃N₃O₂
Molecular Weight	231.25 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	231.100776666 g/mol
Monoisotopic Mass	231.100776666 g/mol
Topological Polar Surface Area	67.2 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	254
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 Information

1 of 2
Drug Name	Marplan
PubMed Health	Isocarboxazid (By mouth)
Drug Classes	Antidepressant
Drug Label	Marplan (isocarboxazid), a monoamine oxidase inhibitor, is available for oral administration in 10-mg tablets. Each tablet also contains lactose, corn starch, povidone, D&C Red No.27, FD&C Yellow No.6, and magnesium stearate. Chemically, isocarbo.
Active Ingredient	Isocarboxazid
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Validus Pharms

2 of 2
Drug Name	Marplan
PubMed Health	Isocarboxazid (By mouth)
Drug Classes	Antidepressant
Drug Label	Marplan (isocarboxazid), a monoamine oxidase inhibitor, is available for oral administration in 10-mg tablets. Each tablet also contains lactose, corn starch, povidone, D&C Red No.27, FD&C Yellow No.6, and magnesium stearate. Chemically, isocarbo.
Active Ingredient	Isocarboxazid
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Validus Pharms

4.2 Drug Indication

Isocarboxazid is indicated for the treatment of the enduring and debilitating symptoms of depression that have not responded to other antidepressant drugs. Depression is a common but serious mood disorder. The patient will present changes in its feelings, thoughts, and ability to handle everyday activities. For a mood disorder to be considered as depression, the symptoms should be present for at least two weeks.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

In vivo and in vitro studies demonstrated isocarboxazid-driven inhibition of MAO in the brain, heart, and liver. The reduced MAO activity, caused by isocarboxazid, results in an increased concentration of serotonin, epinephrine, norepinephrine, and dopamine in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. The increase of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors like isocarboxazid.

5.2 MeSH Pharmacological Classification

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

Monoamine Oxidase Inhibitors

A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414) (See all compounds classified as Monoamine Oxidase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ISOCARBOXAZID

5.3.2 FDA UNII

34237V843T

5.3.3 Pharmacological Classes

Monoamine Oxidase Inhibitors [MoA]; Monoamine Oxidase Inhibitor [EPC]

5.4 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AF - Monoamine oxidase inhibitors, non-selective

N06AF01 - Isocarboxazid

5.5 Absorption, Distribution and Excretion

Absorption

The pharmacokinetic profile of isocarboxazid have not been fully studied but it is suggested that its properties should be fairly similar to the ones of some analogs like phenelzine and tranylcypromine. These drugs are readily absorbed by the GI tract, present a low bioavailability and reach peak concentrations in 1-2 hours.

Route of Elimination

Most of the eliminated dose is found in the urine, accounting for the 42.5% of the administered dose after 24 hours. From this amount, 75% of the renally eliminated drug is in the form of hippuric acid. Another section of the eliminated dose is observed through the intestinal tract and it accounts for 22% of the administered dose after 24 hours.

5.6 Metabolism/Metabolites

The pharmacokinetic profile of isocarboxazid have not been fully studied but it is suggested that its properties should be fairly similar to the ones of some analogs like phenelzine and tranylcypromine. These drugs are rapidly metabolized by acetylation in the liver. As part of the metabolism, hippuric acid is a major metabolite.

5.7 Biological Half-Life

The pharmacokinetic profile of isocarboxazid have not been fully studied but it is suggested that its properties should be fairly similar to the ones of some analogs like phenelzine and tranylcypromine. The isocarboxazid half-life is of little interest as it is an irreversible monoamine oxidase inhibitor. These drugs present a very short half-life of 1.5-4 hours due to rapid hepatic metabolism.

5.8 Mechanism of Action

Isocarboxazid works by irreversibly blocking the action of monoamine oxidases (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase-A (MAO-A) and monoamine oxidase-B (MAO-B). Isocarboxacid, like other monoamine oxidase inhibitors, are unique psychopharmacological agents whose clinical effect is related to the direct action of the monoamine oxidases to transform them into reactive metabolites.

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Lifecare Laboratories Pvt Ltd

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Lifecare Laboratories Pvt Ltd

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About the Company : Lifecare Labs specializes in producing bulk drugs (APIs) and intermediates that adhere to the industry's stringent quality parameters. Its objective is to deliver excellence throug...

Lifecare Labs specializes in producing bulk drugs (APIs) and intermediates that adhere to the industry's stringent quality parameters. Its objective is to deliver excellence through its "quality designed for excellence" mission and meet its customers' requirements. Cost-effectiveness is a top priority for the company, and it aims to establish long-term relationships with its clients. Lifecare Labs possesses state-of-the-art facilities for manufacturing bulk drugs (APIs) and intermediates and has dedicated units for products. Its mission is to become a globally recognized company responsible for its customers, business partners and society.

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