QuickView for Isocarboxazid (compound)

Summary
General Info

PubChem

PubChem Compound 3759

Name:	Isocarboxazid
PubChem Compound ID:	3759
Description:	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)
Molecular formula:	C₁₂H₁₃N₃O₂
Molecular weight:	231.251 g/mol
Synonyms:	Isocarboxazidum [INN-Latin]; 3-Isoxazolecarboxylic acid, 5-methyl-, 2-benzylhydrazide; Maraplan; EINECS 200-438-4; 3-Isoxazolecarboxylic acid, 5-methyl-, 2-(phenylmethyl)hydrazide; Isocarboxazide; Ro 5-0831/1; Isocarbonazid; 1-Benzyl-1-(5-methyl-3-isoxazolylcarbonyl)hydrazine; Isocarbossazide [DCIT]. show more » Isocarboxazidum [INN-Latin]; 3-Isoxazolecarboxylic acid, 5-methyl-, 2-benzylhydrazide; Maraplan; EINECS 200-438-4; 3-Isoxazolecarboxylic acid, 5-methyl-, 2-(phenylmethyl)hydrazide; Isocarboxazide; Ro 5-0831/1; Isocarbonazid; 1-Benzyl-1-(5-methyl-3-isoxazolylcarbonyl)hydrazine; Isocarbossazide [DCIT]; CAS-59-63-2; SPBio_002869; Isocarboxyzid; NSC 169893; Marplon; Isocarboxazida [INN-Spanish]; Benazide; 1-Benzyl-2-(5-methyl-3-isoxazolyl-carbonyl)hydrazine; D02580; Marplan (TN); N'-Benzyl N-methyl-5-isoxazolecarboxylhydrazide-3; Prestwick1_000795; Isocarboxazide [INN-French]; Marplan; 59-63-2; 1-Benzyl-2-(5-methyl-3-isoxazolylcarbonyl)hydrazine; Isocarboxazid [BAN:INN]; NSC169893; Isocarboxazid; 3-Isoxazolecarboxylic acid, 5-methyl-, 2- (phenylmethyl)hydrazide; Isocarbossazide; BMIH; 5-Methyl-3-isoxazolecarboxylic acid 2-benzylhydrazide; Enerzer; Ro 5-0831; Prestwick0_000795; NCGC00016267-01; BRN 0201295; 4-27-00-03999 (Beilstein Handbook Reference) show less «

DrugBank

Identification

Name:	Isocarboxazid
Name (isomeric):	DB01247
Drug Type:	small molecule
Description:	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)
Synonyms:	Isocarbonazid; Isocarboxazidum [INN-Latin]; Isocarbossazide [Dcit]; Isocarboxazide [INN-French]; Isocarboxyzid; Isocarboxazide; Isocarboxazida [INN-Spanish]
Brand:	Marplan, BMIH, Marplon, Maraplan, Benazide, Enerzer
Category:	Antidepressants, Monoamine Oxidase Inhibitors, Antidepressive Agents
CAS number:	59-63-2

Pharmacology

Indication:	May be used to treat major depressive disorder.
Pharmacology:	Isocarboxazid is a non-selective hydrazine monoamine oxidase (MAO) inhibitor used to treat depression. In vivo and in vitro studies demonstrated inhibition of MAO in the brain, heart, and liver. Depression is a complicated disease that is not fully understood. It is thought that depression may be linked to an imbalance of chemicals within the brain... show more » Isocarboxazid is a non-selective hydrazine monoamine oxidase (MAO) inhibitor used to treat depression. In vivo and in vitro studies demonstrated inhibition of MAO in the brain, heart, and liver. Depression is a complicated disease that is not fully understood. It is thought that depression may be linked to an imbalance of chemicals within the brain. When depression occurs, there may be a decrease in the amount of chemicals released from nerve cells in the brain. These chemicals are called monoamines. Monoamines are broken down by a chemical called monoamine oxidase. Isocarboxazid prevents monoamine oxidase from breaking down the monoamines. This results in an increased amount of active monoamines in the brain. By increasing the amount of monoamines in the brain, the imbalance of chemicals thought to be caused by depression is altered. This helps relieve the symptoms of depression. show less «
Mechanism of Action:	Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (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 irrevers... show more » Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (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). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors. show less «
Absorption:	Well absorbed from the gastrointestinal tract.
Biotransformation:	Hepatic and rapid (by oxidation).
Toxicity:	Signs of overdose include severe anxiety, confusion, convulsions, cool clammy skin, severe dizziness, severe drowsiness, fast and irregular pulse, fever, hallucinations, severe headache, high or low blood pressure, hyperactive reflexes, muscle stiffness, respiratory depression or failure, slowed reflexes, sweating, severe trouble in sleeping, and unusual irritability.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals, avoid tyramine, caffeine and alcohol.

Drug interaction:

Naratriptan	The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Methamphetamine	Possible hypertensive crisis
Procaterol	Increased arterial pressure
Ephedrine	Increased arterial pressure
Methylphenidate	Possible hypertensive crisis with this combination

Naratriptan	The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Methamphetamine	Possible hypertensive crisis
Procaterol	Increased arterial pressure
Ephedrine	Increased arterial pressure
Methylphenidate	Possible hypertensive crisis with this combination
Dexfenfluramine	Risk of hypertensive crisis.
Imipramine	Possibility of severe adverse effects
Clomipramine	Possibility of severe adverse effects
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Citalopram	Possible severe adverse reaction with this combination
Tramadol	Tramadol may increase the risk of serotonin syndrome and seizure induction by the MAO inhibitor, isocarboxazid.
Phentermine	Possible hypertensive crisis
Amphetamine	Possible hypertensive crisis
Ephedra	Increased arterial pressure
Phenylephrine	Increased arterial pressure
Amitriptyline	Possibility of severe adverse effects
Mazindol	Possible hypertensive crisis
Amoxapine	Possibility of severe adverse effects
Dopamine	Increased arterial pressure
Escitalopram	Possible severe adverse reaction with this combination
Paroxetine	Possible severe adverse reaction with this combination
Duloxetine	Possible severe adverse reaction with this combination
Trimipramine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Buspirone	Possible blood pressure elevation
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Mirtazapine	Possible severe adverse reaction with this combination
Dobutamine	Increased arterial pressure
Buprenorphine	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like isocarboxazid. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
L-Tryptophan	Possible severe adverse reaction with this combination
Norepinephrine	Increased arterial pressure
Phenylpropanolamine	Increased arterial pressure
Entacapone	Possible hypertensive crisis with this combination
Trimethobenzamide	Trimethobenzamide and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Dextromethorphan	Possible severe adverse reaction
Pirbuterol	Increased arterial pressure
Triprolidine	Triprolidine and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Desipramine	Possibility of severe adverse effects
Galantamine	Possible antagonism of action
Dextroamphetamine	Possible hypertensive crisis
Vilazodone	MAO Inhibitors may enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This may cause serotonin syndrome. Avoid combination.
Trospium	Trospium and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Isocarboxazid, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Midodrine	Possible hypertensive crisis with this combination
Rivastigmine	Possible antagonism of action
Brimonidine	MAO Inhibitors like isocarboxazid may enhance the hypertensive effect of Alpha2-Agonists (Ophthalmic). The concomitant use of monoamine oxidase inhibitors and ophthalmic alpha2 agonists is contraindicated.
Levodopa	Possible hypertensive crisis
Sertraline	Possible severe adverse reaction with this combination
Pseudoephedrine	Increased arterial pressure
Phendimetrazine	Possible hypertensive crisis
Tolcapone	Tolcapone and Isocarboxazid decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
Fluoxetine	Possible severe adverse reaction with this combination
Benzphetamine	MAO Inhibitors may enhance the hypertensive effect of Amphetamines. Concomitant use of amphetamines and monoamine oxidase inhibitors (MAOI) should be avoided. If used concomitantly, careful monitoring of blood pressure must occur. It may take up to 2 weeks after the discontinuation of an MAOI for the effects to dissipate enough to afford safety to the administration of interacting agents.
Bezafibrate	MAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like isocarboxazid.
Protriptyline	Possibility of severe adverse effects
Nefazodone	Possible severe adverse reaction with this combination
Atomoxetine	Possible severe adverse reaction with this combination
Bupropion	Possible severe adverse reaction with this combination
Isoproterenol	Increased arterial pressure
Doxepin	Possibility of severe adverse effects
Donepezil	Possible antagonism of action
Almotriptan	The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, almotriptan. Concomitant therapy is contraindicated.
Fenoterol	Increased arterial pressure
Sibutramine	Possible serotoninergic syndrome with this combination
Rizatriptan	The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, rizatriptan. Concomitant therapy is contraindicated.
Meperidine	Potentially fatal adverse effects
Epinephrine	Increased arterial pressure
Altretamine	Risk of severe hypotension
Salbutamol	Increased arterial pressure
Phenmetrazine	Possible hypertensive crisis
Terbutaline	Increased arterial pressure
Fluvoxamine	Possible severe adverse reaction with this combination
Orciprenaline	Increased arterial pressure
Methotrimeprazine	Possible severe adverse reaction with this combination
Metaraminol	Increased arterial pressure
Methoxamine	Increased arterial pressure
Nortriptyline	Possibility of severe adverse effects
Desvenlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Guanethidine	Isocarboxazid may decrease the effect of guanethidine.
Diethylpropion	Possible hypertensive crisis
Tetrabenazine	Tetrabenazine may increase the adverse/toxic effects of Isocarboxazid. Concomitant therapy is contraindicated.
Zolmitriptan	The MAO inhibitor, isocarboxazid, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing isocarboxazid are contraindicated.
Sumatriptan	The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, sumatriptan. Concomitant therapy is contraindicated.
Venlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Fenfluramine	Possible hypertensive crisis
Mephentermine	Increased arterial pressure

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Targets

Amine oxidase [flavin-containing] A

Amine oxidase [flavin-containing] B