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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
    Isocarboxazid
    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 Weight 231.25 g/mol
    Molecular Formula C12H13N3O2
    XLogP31.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass231.100776666 g/mol
    Monoisotopic Mass231.100776666 g/mol
    Topological Polar Surface Area67.2 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity254
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameMarplan
    PubMed HealthIsocarboxazid (By mouth)
    Drug ClassesAntidepressant
    Drug LabelMarplan (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 IngredientIsocarboxazid
    Dosage FormTablet
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyValidus Pharms

    2 of 2  
    Drug NameMarplan
    PubMed HealthIsocarboxazid (By mouth)
    Drug ClassesAntidepressant
    Drug LabelMarplan (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 IngredientIsocarboxazid
    Dosage FormTablet
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyValidus 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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    ABOUT THIS PAGE

    Isocarboxazid Manufacturers

    A Isocarboxazid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Isocarboxazid, including repackagers and relabelers. The FDA regulates Isocarboxazid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Isocarboxazid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Isocarboxazid manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Isocarboxazid Suppliers

    A Isocarboxazid supplier is an individual or a company that provides Isocarboxazid active pharmaceutical ingredient (API) or Isocarboxazid finished formulations upon request. The Isocarboxazid suppliers may include Isocarboxazid API manufacturers, exporters, distributors and traders.

    click here to find a list of Isocarboxazid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Isocarboxazid USDMF

    A Isocarboxazid DMF (Drug Master File) is a document detailing the whole manufacturing process of Isocarboxazid active pharmaceutical ingredient (API) in detail. Different forms of Isocarboxazid DMFs exist exist since differing nations have different regulations, such as Isocarboxazid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Isocarboxazid DMF submitted to regulatory agencies in the US is known as a USDMF. Isocarboxazid USDMF includes data on Isocarboxazid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Isocarboxazid USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Isocarboxazid suppliers with USDMF on PharmaCompass.

    Isocarboxazid NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Isocarboxazid as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Isocarboxazid API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Isocarboxazid as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Isocarboxazid and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Isocarboxazid NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Isocarboxazid suppliers with NDC on PharmaCompass.

    Isocarboxazid GMP

    Isocarboxazid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Isocarboxazid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Isocarboxazid GMP manufacturer or Isocarboxazid GMP API supplier for your needs.

    Isocarboxazid CoA

    A Isocarboxazid CoA (Certificate of Analysis) is a formal document that attests to Isocarboxazid's compliance with Isocarboxazid specifications and serves as a tool for batch-level quality control.

    Isocarboxazid CoA mostly includes findings from lab analyses of a specific batch. For each Isocarboxazid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Isocarboxazid may be tested according to a variety of international standards, such as European Pharmacopoeia (Isocarboxazid EP), Isocarboxazid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Isocarboxazid USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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