MOCLOBEMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H17ClN2O2
Molecular Weight	268.739
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(C=C1)C(=O)NCCN2CCOCC2

InChI

InChIKey=YHXISWVBGDMDLQ-UHFFFAOYSA-N

InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)

HIDE SMILES / InChI

Molecular Formula	C13H17ClN2O2
Molecular Weight	268.739
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con097060.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7905288

Moclobemide ia an antidepressant that acts on the monoaminergic cerebral neurotransmitter system by reversibly inhibiting monoamine oxidase, primarily type A (RIMA). The metabolism of noradrenaline, dopamine and serotonin is thereby reduced, resulting in increased extracellular concentrations of these neurotransmitters. Increase in the level of serotonin is the most pronounced. Moclobemide administration also leads to increased monoamine receptor stimulation, reversal of reserpine induced behavioral effects, selective depression of the rapid eye movement (REM) sleep, down regulation of beta-adrenoceptors and increases in plasma prolactin and growth hormone levels. It reduces scopolamine-induced performance decrement and alcohol induced performance deficit which suggest a neuroprotective role. Moclobemide is indicated for the treatment of major depressive episodes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con097060.pdf	Inhibitor 8504		0.005 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 179 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con097060.pdf	Palliative		Approved 8583	MOCLOBEMIDE Approved Use Moclobemide is indicated for the treatment of major depressive episodes. Launch Date 2003

C_max

Value	Dose	Co-administered	Analyte	Population
1.05 mg/L CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.94 mg/L CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2.66 mg × h/L CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.36 mg × h/L CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.2 h CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.16 h CLINICAL TRIAL https://www.ingentaconnect.com/contentone/govi/pharmaz/2019/00000074/00000002/art00006?crawler=true&mimetype=application/pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		MOCLOBEMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1550 mg single, oral Overdose Dose: 1550 mg Route: oral Route: single Dose: 1550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	Disc. AE: Stupor, Agitation... AEs leading to discontinuation/dose reduction: Stupor Agitation Disorientation Amnesia Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
20550 mg single, oral Overdose Dose: 20550 mg Route: oral Route: single Dose: 20550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7617806/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7617806/	Sources: https://pubmed.ncbi.nlm.nih.gov/7617806/

AEs

AE	Significance	Dose	Population
Agitation	Disc. AE	1550 mg single, oral Overdose Dose: 1550 mg Route: oral Route: single Dose: 1550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
Amnesia	Disc. AE	1550 mg single, oral Overdose Dose: 1550 mg Route: oral Route: single Dose: 1550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
Disorientation	Disc. AE	1550 mg single, oral Overdose Dose: 1550 mg Route: oral Route: single Dose: 1550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
Stupor	Disc. AE	1550 mg single, oral Overdose Dose: 1550 mg Route: oral Route: single Dose: 1550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/
Nausea	Disc. AE	20550 mg single, oral Overdose Dose: 20550 mg Route: oral Route: single Dose: 20550 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1546127/

PubMed

Title	Date	PubMed
A review of acute treatments for bipolar depression.	2004-05	15107653
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?	2004-04	15078174
Regulation of the human corticotropin-releasing-hormone gene promoter activity by antidepressant drugs in Neuro-2A and AtT-20 cells.	2004-04	14735130
Effect of combined administration of 5-HT1A or 5-HT1B/1D receptor antagonists and antidepressants in the forced swimming test.	2004-03-08	15033385
The effects of moclobemide on autonomic and cognitive functions in healthy volunteers.	2004-03	15048616
Death following acute poisoning by moclobemide.	2004-02-10	15013171
Use of the elevated T-maze to study anxiety in mice.	2004-01-05	14684253
Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation.	2004-01	14697899
Moclobemide and the risk of serotonin toxicity (or serotonin syndrome).	2004	15046013
In vitro metabolism of zolmitriptan in rat cytochromes induced with beta-naphthoflavone and the interaction between six drugs and zolmitriptan.	2003-12-15	14642738
Effects of the antidepressant drug moclobemide on learning and memory in rats.	2003-12	14735229
cDNA gene expression profile of rat hippocampus after chronic treatment with antidepressant drugs.	2003-12	14666413
Antidepressants are functional antagonists at the serotonin type 3 (5-HT3) receptor.	2003-11	14647397
Cytoprotective effect is one of common action pathways for antidepressants.	2003-10	14531941
A high-performance liquid chromatography method with photodiode-array UV detection for therapeutic drug monitoring of the nontricyclic antidepressant drugs.	2003-10	14508379
Moclobemide poisoning: toxicokinetics and occurrence of serotonin toxicity.	2003-10	12968990
Questions & answers. My friend swears by her antidepressant, moclobemide, which she gets from Canada because it is not available in the United States. She is content with the relief she is getting and happy about the absence of sexual side effects. What is moclobemide, and how can I decide whether it would be a good choice for me?	2003-09	14505964
Are gender differences important for the clinical effects of antidepressants?	2003-09	12944340
Possible involvement of opioid receptors in moclobemide-induced hypothermia in mice.	2003-09	12860440
Analysis of eighteen antidepressants, four atypical antipsychotics and active metabolites in serum by liquid chromatography: a simple tool for therapeutic drug monitoring.	2003-08-25	12888196
Efficacy of combined therapy and pharmacotherapy for depressed patients with or without personality disorders.	2003-08-02	12893503
Attenuation of MPTP-induced dopaminergic neurotoxicity by TV3326, a cholinesterase-monoamine oxidase inhibitor.	2003-07	12871570
Pharmacological treatment of frontotemporal dementia: treatment response to the MAO-A inhibitor moclobemide.	2003-07	12833310
Mapping the cerebral monoamine oxidase type A: positron emission tomography characterization of the reversible selective inhibitor [11C]befloxatone.	2003-05	12606609
Pre- and post-treatment with pirlindole and dehydropirlindole protects cultured brain cells against nitric oxide-induced death.	2003-04-11	12679138
Moclobemide in the treatment of hot flashes in postmenopausal women.	2003-04-01	12665046
[Prognostic value of pharmaco-EEG in depression treated with moclobemide].	2003-03-22	12647427
Fatal combination of moclobemide overdose and whisky.	2003-03	12765230
Death following ingestion of MDMA (ecstasy) and moclobemide.	2003-03	12603236
Changes in personality pathology after pharmacotherapy and combined therapy for depressed patients.	2003-02	12659547
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003-01-01	12464242
Antidepressants and driver impairment: empirical evidence from a standard on-the-road test.	2003-01	12590619
Treatment of depression with comorbid anxiety disorders: differential efficacy of paroxetine versus moclobemide.	2003-01	12490770
A preliminary open-label study of moclobemide treatment of pain disorder.	2003	14608245
Antidepressants versus placebo for people with bulimia nervosa.	2003	14583971
Antidepressant-related erectile dysfunction: management via avoidance, switching antidepressants, antidotes, and adaptation.	2003	12971811
[Seasonal affective disorder].	2003	12876991
Antidepressants for smoking cessation.	2003	12804385
Moclobemide: therapeutic use and clinical studies.	2003	12595913
Efficacy of citalopram and moclobemide in patients with social phobia: some preliminary findings.	2002-12	12457375
LC determination of moclobemide and three metabolites in plasma.	2002-11-07	12408918
The lack of a placebo effect in a trial of fluoxetine in the treatment of fibromyalgia.	2002-11	12459412
Limited potentiation of blood pressure response to oral tyramine by brain-selective monoamine oxidase A-B inhibitor, TV-3326 in conscious rabbits.	2002-11	12423669
World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the pharmacological treatment of anxiety, obsessive-compulsive and posttraumatic stress disorders.	2002-10	12516310
Moclobemide discontinuation syndrome predominantly presenting with influenza-like symptoms.	2002-09	12236637
Moclobemide response in depressed patients: association study with a functional polymorphism in the monoamine oxidase A promoter.	2002-07	12163988
Moclobemide is effective and well tolerated in the long-term pharmacotherapy of social anxiety disorder with or without comorbid anxiety disorder.	2002-07	12131599
[Serotonin syndrome--several cases of this often overlooked diagnosis].	2002-06-30	12555608
Moclobemide: evolution, pharmacodynamic, and pharmacokinetic properties.	2002	12353059
Clinical pharmacokinetics of intranasal sumatriptan.	2002	12190330

Patents

Sample Use Guides

In Vivo Use Guide

Initial usual dose for adults is 300 mg, administered in divided doses after meals. The tablets should be taken with fluid. If necessary, the daily dose can be increased to 600 mg per day.

Route of Administration: Oral

In Vitro Use Guide

The inhibition of monoamine oxidase (MAO) in rat liver by the short-acting MAO-A inhibitor moclobemide, administered p.o. at roughly equieffective doses 2 h before decapitation, was investigated for its reversibility under various in vitro conditions. MAO A activity in liver homogenates, inhibited by moclobemide (300 mumol/kg) to approx. 15% of control, time dependently recovered during 0.5 to 2 h of incubation at 37 degrees C, irrespective of whether the homogenates were prepared and incubated in distilled water or Krebs-Ringer buffer. Dialysis of such homogenates for 4 h in distilled water at 37 degrees C (but not at 13 degrees C) led to a complete return of the MAO activity.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:02 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:02 GMT 2025`
Record UNII	PJ0Y7AZB63
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MOCLOBEMIDE

Official Name

English

AURORIX

Preferred Name

English

MOCLOBEMIDE [MART.]

Common Name

English

Moclobemide [WHO-DD]

Common Name

English

4-Chloro-N-(2-morpholinoethyl)benzamide

Systematic Name

English

GNF-PF-695

Code

English

RO-11-1163/000

Code

English

RO 11-1163/000

Code

English

BENZAMIDE, 4-CHLORO-N-(2-(4-MORPHOLINYL)ETHYL)-

Systematic Name

English

MOCLOBEMIDE [MI]

Common Name

English

MOCLOBEMIDE [HSDB]

Common Name

English

RO-111163000

Code

English

P-CHLORO-N-(2-MORPHOLINOETHYL)BENZAMIDE

Common Name

English

moclobemide [INN]

Common Name

English

MOCLOBEMIDE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667