QuickView for Moclobemide (compound)

Summary
General Info

PubChem

PubChem Compound 4235

Name:	Moclobemide
PubChem Compound ID:	4235
Description:	A reversible inhibitor of monoamine oxidase type A; (RIMA); (see MONOAMINE OXIDASE INHIBITORS) that has antidepressive properties.
Molecular formula:	C₁₃H₁₇ClN₂O₂
Molecular weight:	268.739 g/mol
Synonyms:	SMR000012114; Moclobemide [USAN:BAN:INN]; MLS000070549; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; Manerix; 4-Chlor-N-(2-morpholinoethyl)benzamid; Moclobemidum [INN-Latin]; Benzamide, 4-chloro-N-(2-(4-morpholinyl)ethyl)-; CBMicro_048319; Aurorix. show more » SMR000012114; Moclobemide [USAN:BAN:INN]; MLS000070549; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; Manerix; 4-Chlor-N-(2-morpholinoethyl)benzamid; Moclobemidum [INN-Latin]; Benzamide, 4-chloro-N-(2-(4-morpholinyl)ethyl)-; CBMicro_048319; Aurorix; Aurorix (TN); Moclobemide (USAN); Ro 11-1163/000; Moclobemide; HSDB 7180; D02561; BRN 0530974; Ro 11-1163; 71320-77-9; Moclobemid; Moclobemida [INN-Spanish]; BIM-0048213.P001; p-Chloro-N-(2-morpholinoethyl)benzamide; BAS 03214735; Ro-11-1163; 4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide; Moclamine show less «

DrugBank

Identification

Name:	Moclobemide
Name (isomeric):	DB01171
Drug Type:	small molecule
Description:	A reversible inhibitor of monoamine oxidase type A; (RIMA); (see MONOAMINE OXIDASE INHIBITORS) that has antidepressive properties.
Synonyms:	Moclobemide [Usan:Ban:Inn]; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; Moclamide; Moclaime; Moclobemid; Moclobemida [INN-Spanish]; 4-Chlor-N-(2-morpholinoethyl)benzamid; p-Chloro-N-(2-morpholinoethyl)benzamide; Moclobemidum [INN-Latin]; 4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide. show more » Moclobemide [Usan:Ban:Inn]; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; Moclamide; Moclaime; Moclobemid; Moclobemida [INN-Spanish]; 4-Chlor-N-(2-morpholinoethyl)benzamid; p-Chloro-N-(2-morpholinoethyl)benzamide; Moclobemidum [INN-Latin]; 4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide; Moclamine show less «
Brand:	Manerix, Aurorix
Category:	Monoamine Oxidase Inhibitors, Antidepressive Agents
CAS number:	71320-77-9

Pharmacology

Indication:	For the treatment of depression.
Pharmacology:	Moclobemide belongs to a class of MAOI antidepressants known as reversible inhibitors of monoamine oxidase type-A (RIMAs). The primary role of monoamine oxidase MAO lies in the metabolism of and regulation of the levels of monoamines (serotonin, norepinephrine, and dopamine). Within neurons, MAO appears to regulate the levels of monoamines released... show more » Moclobemide belongs to a class of MAOI antidepressants known as reversible inhibitors of monoamine oxidase type-A (RIMAs). The primary role of monoamine oxidase MAO lies in the metabolism of and regulation of the levels of monoamines (serotonin, norepinephrine, and dopamine). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms. RIMAs demonstrate transient inhibition of the substrate binding site of MAO-A as well as competitive displacement from this site by bioamines. The RIMAs are distinguished from the older monoamine oxidase inhibitors (MAOIs) by their selectivity and reversibility. show less «
Mechanism of Action:	The mechanism of action of moclobemide involves the selective, reversible inhibition of MAO-A. This inhibition leads to a decrease in the metabolism and destruction of monoamines in the neurotransmitters. This results in an increase in the monoamines, relieving depressive symptoms.
Absorption:	Well absorbed from the gastrointestinal tract (> 95%). The presence of food reduces the rate but not the extent of absorption. Hepatic first pass metabolism reduces bioavailability to 45-70% following administration of a single dose, but increases to 80% with multiple dosing as a result of saturation of the first pass effect. Peak plasma concentrations are reached within 1 - 2 hours following oral administration.
Protein binding:	Approximately 50% (primarily to albumin)
Biotransformation:	Moclobemide is almost completely metabolized in the liver by Cytochrome P450 2C19 and 2D6.
Half Life:	1-2 hours (4 hours in cirrhotic patients); metabolites are renally excreted
Toxicity:	LD50 (mouse) is 730mg/kg and LD50 (rat) is 1,300mg/kg. Signs of toxicity include hypertension, drowsiness, dizziness, confusion, tremors, headache, agitation, muscle rigidity and seizures.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Food slows absorption a little. Avoid alcohol. Take after meals in order to minimize the risk of interaction with tyramine.

Drug interaction:

Rizatriptan	The MAO inhibitor, moclobemide, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, rizatriptan. Concomitant therapy is contraindicated.
Protriptyline	Possible severe adverse reaction with this combination
Selegiline	Decrease in selectivity
Tetrabenazine	Tetrabenazine may increase the adverse/toxic effects of Moclobemide. Concomitant therapy is contraindicated.
Amitriptyline	Possible severe adverse reaction with this combination

Rizatriptan	The MAO inhibitor, moclobemide, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, rizatriptan. Concomitant therapy is contraindicated.
Protriptyline	Possible severe adverse reaction with this combination
Selegiline	Decrease in selectivity
Tetrabenazine	Tetrabenazine may increase the adverse/toxic effects of Moclobemide. Concomitant therapy is contraindicated.
Amitriptyline	Possible severe adverse reaction with this combination
Bezafibrate	MAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like moclobemide.
Meperidine	Increased CNS toxicity (can cause death)
Citalopram	Possible serotoninergic syndrome
Norepinephrine	Moclobemide increases the sympathomimetic effect of norepinephrine.
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Mephentermine	Moclobemide increases the sympathomimetic effect of mephentermine.
Paroxetine	Possible severe adverse reaction with this combination
Buprenorphine	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like moclobemide. 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.
Orciprenaline	Moclobemide increases the sympathomimetic effect of orciprenaline.
Trospium	Trospium and Moclobemide, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
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.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dobutamine	Moclobemide increases the sympathomimetic effect of dobutamine.
Methoxamine	Moclobemide increases the sympathomimetic effect of methoxamine.
Cimetidine	Cimetidine may increase the serum concentration of moclobemide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of moclobemide if cimetidine is initiated, discontinued or dose changed.
Triprolidine	Triprolidine and Moclobemide, 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.
Salbutamol	Moclobemide increases the sympathomimetic effect of salbutamol.
Galantamine	Possible antagonism of action
Fluvoxamine	Increased incidence of adverse effects with this association
Imipramine	Possible severe adverse reaction with this combination
Tolcapone	Tolcapone and Moclobemide 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.
Dopamine	Moclobemide increases the sympathomimetic effect of dopamine.
Ephedra	Moclobemide increases the sympathomimetic effect of ephedra.
Amoxapine	Possible severe adverse reaction with this combination
Ephedrine	Moclobemide increases the sympathomimetic effect of ephedrine.
Ticlopidine	Ticlopidine may decrease the metabolism and clearance of Moclobemide. Consider alternate therapy or monitor for adverse/toxic effects of Moclobemide if Ticlopidine is initiated, discontinued or dose changed.
Tryptophanyl-5'amp	Possible severe adverse reaction with this combination
Terbutaline	Moclobemide increases the sympathomimetic effect of terbutaline.
Rivastigmine	Possible antagonism of action
Sertraline	Possible severe adverse reaction with this combination
Pseudoephedrine	Moclobemide increases the sympathomimetic effect of pseudoephedrine.
Zolmitriptan	The MAO inhibitor, moclobemide, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing moclobemide are contraindicated.
Clomipramine	Possible severe adverse reaction with this combination
Metaraminol	Moclobemide increases the sympathomimetic effect of metaraminol.
Trimethobenzamide	Trimethobenzamide and Moclobemide, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Nortriptyline	Possible severe adverse reaction with this combination
Doxepin	Possible severe adverse reaction with this combination
Fenoterol	Moclobemide increases the sympathomimetic effect of fenoterol.
Donepezil	Possible antagonism of action
Pirbuterol	Moclobemide increases the sympathomimetic effect of pirbuterol.
Sibutramine	Possible serotoninergic syndrome with this combination
Brimonidine	MAO Inhibitors like moclobemide may enhance the hypertensive effect of Alpha2-Agonists (Ophthalmic). The concomitant use of monoamine oxidase inhibitors and ophthalmic alpha2 agonists is contraindicated.
Dextromethorphan	Increased CNS toxicity
Terbinafine	Terbinafine may reduce the metabolism and clearance of Moclobemide. Consider alternate therapy or monitor for therapeutic/adverse effects of Moclobemide if Terbinafine is initiated, discontinued or dose changed.
Phenylephrine	Moclobemide increases the sympathomimetic effect of phenylephrine.
Procaterol	Moclobemide increases the sympathomimetic effect of procaterol.
Fluoxetine	Risk of serotoninergic syndrome
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Moclobemide, 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.
Desipramine	Possible severe adverse reaction with this combination
Phenylpropanolamine	Moclobemide increases the sympathomimetic effect of phenylpropanolamine.
Isoproterenol	Moclobemide increases the sympathomimetic effect of isoproterenol.
Desvenlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Epinephrine	Moclobemide increases the sympathomimetic effect of epinephrine.
Tramadol	Tramadol may increase the risk of serotonin syndrome and seizure induction by the MAO inhibitor, moclobemide.
Venlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.

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Targets

Amine oxidase [flavin-containing] A

Enzymes

Amine oxidase [flavin-containing] A

Amine oxidase [flavin-containing] B