Moclobemide

Summary

Moclobemide (CHEMBL86304) is an approved small-molecule antidepressant (ATC N06AG02) targeting MAOA and MAOB; indicated across 7 conditions including depressive disorder and anxiety.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N06AG02
• Targets: 2 (MAOA, MAOB)
• Indications: 7 conditions
• Clinical trials: 4
• Chemistry: 268.74 Da · C13H17ClN2O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL86304
Name	Moclobemide
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4235
ChEBI	CHEBI:83531
ATC	N06AG02
Molecular formula	C13H17ClN2O2
Molecular weight	268.74
InChIKey	YHXISWVBGDMDLQ-UHFFFAOYSA-N

SMILES: C1COCCN1CCNC(=O)C2=CC=C(C=C2)Cl

IUPAC name: 4-chloro-N-(2-morpholin-4-ylethyl)benzamide

ChEBI definition: A member of the class of benzamides that is benzamide substituted by a chloro group at position 4 and a 2-(morpholin-4-yl)ethyl group at the nitrogen atom. It acts as a reversible monoamine oxidase inhibitor and is used in the treatment of depression.

Pharmacological roles (ChEBI): antidepressant.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant.

Also known as: Aurorix, GNF-PF-695, Manerix, Moclobemida, Moclobemide, RO-111163000, moclobemide, GNF-Pf-695, SID846440, SID90340853, SID104171398, SID50086440

Patent coverage: 3,816 distinct patent families (13,492 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
MAOA	Monoamine oxidase A	Inhibition	8.3	0.2%	P21397
MAOB	Monoamine oxidase B	Inhibition	5.97	0%	P27338

Broader ChEMBL bioactivity targets: 9 (assay-derived). Sample: Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] B, 5-hydroxytryptamine receptor 1A, Voltage-gated inwardly rectifying potassium channel KCNH2, Amine oxidase [flavin-containing] B, Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] A, Aldehyde dehydrogenase 1A1, Programmed cell death 1 ligand 1.

Bioactivity

ChEMBL activities: 30 potent at pChembl ≥ 5 of 48 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
MAOA	9.3	Ki	0.5	nM	CHEMBL_ACT_25111693
MAOA	8.3	Ki	5	nM	CHEMBL_ACT_13478481
P21396	8.3	Ki	5	nM	CHEMBL_ACT_3088850
MAOA	8.3	Ki	5	nM	CHEMBL_ACT_6259885
P21396	8.26	Ki	5.53	nM	CHEMBL_ACT_3068544
MAOA	7.85	Ki	14	nM	CHEMBL_ACT_15050674
MAOA	7	Ki	100	nM	CHEMBL_ACT_22811621
MAOA	6.99	Ki	102	nM	CHEMBL_ACT_18728744
MAOA	6.96	Ki	110	nM	CHEMBL_ACT_16513009
MAOA	6.44	IC50	360	nM	CHEMBL_ACT_25461183
MAOB	5.97	Ki	1080	nM	CHEMBL_ACT_13478460
P19643	5.97	Ki	1080	nM	CHEMBL_ACT_3068568
P19643	5.97	Ki	1080	nM	CHEMBL_ACT_3088851
MAOB	5.97	Ki	1080	nM	CHEMBL_ACT_6259909
MAOB	5.87	Ki	1340	nM	CHEMBL_ACT_15050702
MAOB	5.65	Ki	2240	nM	CHEMBL_ACT_16513022
MAOA	5.44	IC50	3614	nM	CHEMBL_ACT_16483359
P21396	5.41	IC50	3900	nM	CHEMBL_ACT_2391725
CD274	5.41	IC50	3865	nM	CHEMBL_ACT_25852050
P21396	5.41	IC50	3900	nM	CHEMBL_ACT_2593480
MAOB	5.38	Ki	4220	nM	CHEMBL_ACT_18728731
MAOA	5.33	IC50	4664	nM	CHEMBL_ACT_22753934
HTR1A	5.3	Kd	5012	nM	CHEMBL_ACT_2930075
P21396	5.24	IC50	5700	nM	CHEMBL_ACT_3068532
MAOA	5.22	IC50	6061	nM	CHEMBL_ACT_18380661
MAOA	5.22	IC50	6061	nM	CHEMBL_ACT_24886560
P21396	5.2	IC50	6300	nM	CHEMBL_ACT_18680295
P21396	5.17	IC50	6800	nM	CHEMBL_ACT_3123707
MAOB	5.12	Ki	7660	nM	CHEMBL_ACT_22811663
P21396	5	IC50	10000	nM	CHEMBL_ACT_12654763

Target pathways

Aggregated over 2 target gene(s): MAOA, MAOB.

Top Reactome pathways

23 total, by targets touching each:

Pathway	Targets	Genes
Amine Oxidase reactions	2	MAOA, MAOB
Biogenic amines are oxidatively deaminated to aldehydes by MAOA and MAOB	2	MAOA, MAOB
Metabolism	2	MAOA, MAOB
Biological oxidations	2	MAOA, MAOB
Phase I - Functionalization of compounds	2	MAOA, MAOB
Neurotransmitter release cycle	1	MAOA
Neurotransmitter clearance	1	MAOA
Transmission across Chemical Synapses	1	MAOA
Neuronal System	1	MAOA
Cytokine Signaling in Immune system	1	MAOA
Disease	1	MAOA
Immune System	1	MAOA
Norepinephrine Neurotransmitter Release Cycle	1	MAOA
Enzymatic degradation of dopamine by COMT	1	MAOA
Enzymatic degradation of Dopamine by monoamine oxidase	1	MAOA
Dopamine clearance from the synaptic cleft	1	MAOA
Metabolism of serotonin	1	MAOA
Serotonin clearance from the synaptic cleft	1	MAOA
Signaling by Interleukins	1	MAOA
Defective MAOA causes BRUNS	1	MAOA
Metabolic disorders of biological oxidation enzymes	1	MAOA
Diseases of metabolism	1	MAOA
Interleukin-4 and Interleukin-13 signaling	1	MAOA

Dominant GO biological processes

GO term	Targets
dopamine catabolic process	2
biogenic amine metabolic process	1
positive regulation of signal transduction	1
serotonin catabolic process	1
catecholamine metabolic process	1
substantia nigra development	1
hydrogen peroxide biosynthetic process	1

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
depressive disorder	4	MONDO:0002050	MONDO:0002050

4 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
anxiety	3	MONDO:0011918	EFO:0005230
dementia	3	MONDO:0001627	HP:0000726
nicotine dependence	2	MONDO:0008575	EFO:0003768
drug dependence	2	MONDO:0005303	EFO:0003890

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE3	2
PHASE2	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00534573	PHASE3	COMPLETED	Benzamide Derivates as Treatment of Clozapine-induced Hypersalivation
NCT02374567	PHASE3	TERMINATED	Pharmacovigilance in Gerontopsychiatric Patients
NCT01926626	PHASE2	COMPLETED	Evaluation of Moclobemide, a Reversible MAO-A Inhibitor, as an Adjunct to Nicotine Replacement Therapy in Female Smokers
NCT03010761	PHASE2	TERMINATED	Establishment of Cessation Therapy by Clinical Trials for Subjects With Betel-quid Dependence and Oral Pre-cancer

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of DPWG Guideline for moclobemide and CYP2C19	DPWG	CYP2C19

PharmGKB also curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

174 molecules share ≥1 primary target. Top 100 by shared-target count:

Molecule	Source	Status	Shared targets
TEDIZOLID	ChEMBL + PubChem	Phase 4 (approved)	MAOA, MAOB
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
DANTHRON	ChEMBL	Phase 4 (approved)	MAOA, MAOB
FENTANYL	ChEMBL	Phase 4 (approved)	MAOA, MAOB
IPRONIAZID	ChEMBL	Phase 4 (approved)	MAOA, MAOB
LINEZOLID	ChEMBL	Phase 4 (approved)	MAOA, MAOB
MENADIONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
METHYLENE BLUE CATION	ChEMBL	Phase 4 (approved)	MAOA, MAOB
MICONAZOLE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PARGYLINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PHENELZINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PIOGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PRIMAQUINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
RASAGILINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
ROSIGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
SAFINAMIDE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
SELEGILINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TOLOXATONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TRANYLCYPROMINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TROGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
CURCUMIN	ChEMBL	Phase 3	MAOA, MAOB
IDAZOXAN	ChEMBL	Phase 3	MAOA, MAOB
QUERCETIN	ChEMBL	Phase 3	MAOA, MAOB
RESVERATROL	ChEMBL	Phase 3	MAOA, MAOB
BROFAROMINE	ChEMBL	Phase 2	MAOA, MAOB
CIGLITAZONE	ChEMBL	Phase 2	MAOA, MAOB
CLORGILINE	ChEMBL	Phase 2	MAOA, MAOB
DAIDZEIN	ChEMBL	Phase 2	MAOA, MAOB
FORMONONETIN	ChEMBL	Phase 2	MAOA, MAOB
GENISTEIN	ChEMBL	Phase 2	MAOA, MAOB
LADOSTIGIL	ChEMBL	Phase 2	MAOA, MAOB
LUTEOLIN	ChEMBL	Phase 2	MAOA, MAOB
MOFEGILINE	ChEMBL	Phase 2	MAOA, MAOB
PHENAMAZOLINE	ChEMBL	Phase 2	MAOA, MAOB
PIPERINE	ChEMBL	Phase 2	MAOA, MAOB
SEMBRAGILINE	ChEMBL	Phase 2	MAOA, MAOB
SUTEZOLID	ChEMBL	Phase 2	MAOA, MAOB
TIOXOLONE	ChEMBL	Phase 2	MAOA, MAOB
CRIZOTINIB	ChEMBL + PubChem	Phase 4 (approved)	MAOA
REGORAFENIB	ChEMBL + PubChem	Phase 4 (approved)	MAOA
TAFAMIDIS	ChEMBL + PubChem	Phase 4 (approved)	MAOA
ABROCITINIB	ChEMBL	Phase 4 (approved)	MAOA
AMILORIDE	ChEMBL	Phase 4 (approved)	MAOA
ANISINDIONE	ChEMBL	Phase 4 (approved)	MAOA
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	MAOA
ATALUREN	ChEMBL	Phase 4 (approved)	MAOA
BENOXAPROFEN	ChEMBL	Phase 4 (approved)	MAOA
BIFONAZOLE	ChEMBL	Phase 4 (approved)	MAOA
CABOZANTINIB	ChEMBL	Phase 4 (approved)	MAOA
CHLOROPROCAINE	ChEMBL	Phase 4 (approved)	MAOA
COCAINE	ChEMBL	Phase 4 (approved)	MAOA
DEBRISOQUIN	ChEMBL	Phase 4 (approved)	MAOA
DELAVIRDINE	ChEMBL	Phase 4 (approved)	MAOA
DEQUALINIUM	ChEMBL	Phase 4 (approved)	MAOA
DEXTROAMPHETAMINE	ChEMBL	Phase 4 (approved)	MAOA
DISULFIRAM	ChEMBL	Phase 4 (approved)	MAOA
DONEPEZIL	ChEMBL	Phase 4 (approved)	MAOB
ETHOPROPAZINE	ChEMBL	Phase 4 (approved)	MAOA
ETHYNODIOL DIACETATE	ChEMBL	Phase 4 (approved)	MAOA
FAMOTIDINE	ChEMBL	Phase 4 (approved)	MAOA
GUANABENZ	ChEMBL	Phase 4 (approved)	MAOA
GUANFACINE	ChEMBL	Phase 4 (approved)	MAOA
HYDRALAZINE	ChEMBL	Phase 4 (approved)	MAOA
IDEBENONE	ChEMBL	Phase 4 (approved)	MAOA
ISTRADEFYLLINE	ChEMBL	Phase 4 (approved)	MAOB
LAMOTRIGINE	ChEMBL	Phase 4 (approved)	MAOA
LEFLUNOMIDE	ChEMBL	Phase 4 (approved)	MAOA
LYNESTRENOL	ChEMBL	Phase 4 (approved)	MAOA
METAXALONE	ChEMBL	Phase 4 (approved)	MAOA
METHOPHOLINE	ChEMBL	Phase 4 (approved)	MAOA
METHOXSALEN	ChEMBL	Phase 4 (approved)	MAOA
METHYLENE BLUE	ChEMBL	Phase 4 (approved)	MAOA
MEXILETINE	ChEMBL	Phase 4 (approved)	MAOA
NABUMETONE	ChEMBL	Phase 4 (approved)	MAOA
NICLOSAMIDE	ChEMBL	Phase 4 (approved)	MAOA
NIFEDIPINE	ChEMBL	Phase 4 (approved)	MAOA
NITAZOXANIDE	ChEMBL	Phase 4 (approved)	MAOA
NITROFURANTOIN	ChEMBL	Phase 4 (approved)	MAOA
PENTAMIDINE	ChEMBL	Phase 4 (approved)	MAOA
PHENOXYPROPAZINE	ChEMBL	Phase 4 (approved)	MAOA
PONATINIB	ChEMBL	Phase 4 (approved)	MAOA
PROCAINE	ChEMBL	Phase 4 (approved)	MAOA
PROPARACAINE	ChEMBL	Phase 4 (approved)	MAOA
PYRANTEL	ChEMBL	Phase 4 (approved)	MAOA
PYRVINIUM	ChEMBL	Phase 4 (approved)	MAOA
SERTINDOLE	ChEMBL	Phase 4 (approved)	MAOA
SIROLIMUS	ChEMBL	Phase 4 (approved)	MAOA
SORAFENIB	ChEMBL	Phase 4 (approved)	MAOA
STIRIPENTOL	ChEMBL	Phase 4 (approved)	MAOA
TEGASEROD	ChEMBL	Phase 4 (approved)	MAOA
TERIFLUNOMIDE	ChEMBL	Phase 4 (approved)	MAOA
TETRACAINE	ChEMBL	Phase 4 (approved)	MAOA
THIORIDAZINE	ChEMBL	Phase 4 (approved)	MAOA
TIAPROFENIC ACID	ChEMBL	Phase 4 (approved)	MAOA
TRIMETREXATE	ChEMBL	Phase 4 (approved)	MAOA
TRIOXSALEN	ChEMBL	Phase 4 (approved)	MAOA
VARDENAFIL	ChEMBL	Phase 4 (approved)	MAOA
XANOMELINE	ChEMBL	Phase 4 (approved)	MAOA
ZONISAMIDE	ChEMBL	Phase 4 (approved)	MAOB
2-HYDROXYPROPYL-BETA-CYCLODEXTRIN	ChEMBL	Phase 3	MAOA