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 49 Target ID: CHEMBL1951 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con097060.pdf	Inhibitor 8297		0.005 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con097060.pdf	Palliative		Approved 8429	MOCLOBEMIDE Approved Use Moclobemide is indicated for the treatment of major depressive episodes. Launch Date 2003

PubMed

Title	Date	PubMed
Antidepressant-induced sexual dysfunction during treatment with moclobemide, paroxetine, sertraline, and venlafaxine.	2000 Apr	10830148
Meta-analytical studies on new antidepressants.	2001	11719915
A fatal case of serotonin syndrome after combined moclobemide-citalopram intoxication.	2001 Mar	11300508
Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism.	2001 May 18	11412837
Antidepressants in social anxiety disorder.	2001 Sep	11588653
Antidepressants for smoking cessation.	2002	11869562
Treatment of comorbid opiate addiction and attention-deficit hyperactivity disorder (residual type) with moclobemide: a case report.	2002 Apr	11999916
Efficacy of citalopram and moclobemide in patients with social phobia: some preliminary findings.	2002 Dec	12457375
The influence on treatment gain of comorbid avoidant personality disorder in patients with social phobia.	2002 Jan	11838470
Pharmacotherapy of social anxiety disorder.	2002 Jan 1	11801236
Interactive model of therapeutic response in panic disorder: moclobemide, a case in point.	2002 Jun	12006898
Antidepressant side effects in depression patients treated in a naturalistic setting: a study of bupropion, moclobemide, paroxetine, sertraline, and venlafaxine.	2002 Mar	11926080
Characterization of the discriminable stimulus produced by 2-BFI: effects of imidazoline I(2)-site ligands, MAOIs, beta-carbolines, agmatine and ibogaine.	2002 Mar	11877331
Differential effects of chronic antidepressant treatments on micro- and delta-opioid receptors in rat brain.	2002 May 17	12044796
[Seasonal affective disorder].	2003	12876991
Analysis of eighteen antidepressants, four atypical antipsychotics and active metabolites in serum by liquid chromatography: a simple tool for therapeutic drug monitoring.	2003 Aug 25	12888196
cDNA gene expression profile of rat hippocampus after chronic treatment with antidepressant drugs.	2003 Dec	14666413
In vitro metabolism of zolmitriptan in rat cytochromes induced with beta-naphthoflavone and the interaction between six drugs and zolmitriptan.	2003 Dec 15	14642738
Attenuation of MPTP-induced dopaminergic neurotoxicity by TV3326, a cholinesterase-monoamine oxidase inhibitor.	2003 Jul	12871570
Antidepressants are functional antagonists at the serotonin type 3 (5-HT3) receptor.	2003 Nov	14647397
Moclobemide: therapeutic use and clinical studies.	2003 Spring	12595913
Effect of combined administration of 5-HT1A or 5-HT1B/1D receptor antagonists and antidepressants in the forced swimming test.	2004 Mar 8	15033385

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 `Fri Dec 15 14:57:49 GMT 2023` Edited by `admin` on `Fri Dec 15 14:57:49 GMT 2023`
Record UNII	PJ0Y7AZB63
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MOCLOBEMIDE

Official 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

AURORIX

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667