Citalopram

Summary

Citalopram (CHEMBL549) is an approved small molecule (ATC N06AB04) targeting SLC6A4; indicated across 21 conditions including major depressive disorder and depressive disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N06AB04
• Targets: 1 (SLC6A4)
• Indications: 21 conditions
• Clinical trials: 158
• Chemistry: 324.4 Da · C20H21FN2O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL549
Name	Citalopram
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2771
ChEBI	CHEBI:77397
ATC	N06AB04
Molecular formula	C20H21FN2O
Molecular weight	324.4
InChIKey	WSEQXVZVJXJVFP-UHFFFAOYSA-N

SMILES: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F

IUPAC name: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile

ChEBI definition: A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.

Also known as: Citadur, Citalopram, citalopram, SID855965, SID90340852, SID50104852, rac-citalopram, CITALOPRAM, SID174007166, (+/-)-Citalopram, ESCITALOPRAM OXALATE, rac-Citalopram

Parent form; salt/anhydrous children: CHEMBL1200781, CHEMBL1628605

Patent coverage: 8,983 distinct patent families (33,242 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 33,197 (100%) of the total. 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
SLC6A4	SERT	Inhibition	8.3	0.7%	P31645

Broader ChEMBL bioactivity targets: 32 (assay-derived). Sample: Survival motor neuron protein, NPC intracellular cholesterol transporter 1, 5-hydroxytryptamine receptor 2B, Histamine H2 receptor, D(1A) dopamine receptor, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, Acetylcholinesterase, Sodium-dependent noradrenaline transporter.

Bioactivity

ChEMBL activities: 76 potent at pChembl ≥ 5 of 92 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
SLC6A4	9.32	Ki	0.48	nM	CHEMBL_ACT_7695150
SLC6A4	9.04	IC50	0.9	nM	CHEMBL_ACT_7695149
P31652	8.82	Ki	1.5	nM	CHEMBL_ACT_612629
P31652	8.8	Ki	1.6	nM	CHEMBL_ACT_1422527
SLC6A4	8.8	Ki	1.6	nM	CHEMBL_ACT_22850856
SLC6A4	8.8	Ki	1.6	nM	CHEMBL_ACT_512920
P31652	8.74	IC50	1.8	nM	CHEMBL_ACT_121517
P31652	8.71	Ki	1.94	nM	CHEMBL_ACT_3403705
Q60857	8.54	Ki	2.9	nM	CHEMBL_ACT_199301
P31652	8.52	IC50	3	nM	CHEMBL_ACT_13846729
SLC6A4	8.52	IC50	3	nM	CHEMBL_ACT_22967063
SLC6A4	8.52	AC50	3	nM	CHEMBL_ACT_25151030
P31652	8.5	IC50	3.17	nM	CHEMBL_ACT_3217749
P31652	8.41	IC50	3.9	nM	CHEMBL_ACT_12168527
SLC6A4	8.36	Ki	4.38	nM	CHEMBL_ACT_2348889
SLC6A4	8.36	Ki	4.38	nM	CHEMBL_ACT_2571709
SLC6A4	8.24	IC50	5.81	nM	CHEMBL_ACT_24416219
SLC6A4	8.2	IC50	6.27	nM	CHEMBL_ACT_18291222
SLC6A4	8.17	IC50	6.7	nM	CHEMBL_ACT_17998833
SLC6A4	8.09	AC50	8.2	nM	CHEMBL_ACT_25149831
SLC6A4	8.04	IC50	9.2	nM	CHEMBL_ACT_26036266
P31652	8.03	IC50	9.45	nM	CHEMBL_ACT_29098138
KCNH2	8	IC50	10	nM	CHEMBL_ACT_13828643
SLC6A4	7.87	IC50	13.41	nM	CHEMBL_ACT_20667772
SLC6A4	7.8	Ki	16	nM	CHEMBL_ACT_12682774
SLC6A4	7.72	IC50	19	nM	CHEMBL_ACT_5219263
SLC6A4	7.48	Ki	32.8	nM	CHEMBL_ACT_2348897
SLC6A4	7.48	Ki	32.8	nM	CHEMBL_ACT_2571718
SLC6A4	7.23	IC50	59	nM	CHEMBL_ACT_23305404
SLC6A4	7.05	IC50	90	nM	CHEMBL_ACT_13852383

Target pathways

Aggregated over 1 target gene(s): SLC6A4.

Top Reactome pathways

5 total, by targets touching each:

Pathway	Targets	Genes
Neurotransmitter clearance	1	SLC6A4
Transmission across Chemical Synapses	1	SLC6A4
Neuronal System	1	SLC6A4
Serotonin clearance from the synaptic cleft	1	SLC6A4
SLC-mediated transport of neurotransmitters	1	SLC6A4

Dominant GO biological processes

GO term	Targets
response to hypoxia	1
neurotransmitter transport	1
amino acid transport	1
response to nutrient	1
memory	1
circadian rhythm	1
response to xenobiotic stimulus	1
response to toxic substance	1
positive regulation of gene expression	1
positive regulation of serotonin secretion	1
obsolete monoamine transport	1
negative regulation of cerebellar granule cell precursor proliferation	1
negative regulation of synaptic transmission, dopaminergic	1
response to estradiol	1
sodium ion transmembrane transport	1

Indications & clinical

Indications

21 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
major depressive disorder	4	MONDO:0002009	MONDO:0002009
depressive disorder	4	MONDO:0002050	MONDO:0002050
stroke disorder	3	MONDO:0005098	EFO:0000712
obsessive-compulsive disorder	3	MONDO:0008114	EFO:0004242
anxiety	3	MONDO:0011918	EFO:0005230
dementia	3	MONDO:0001627	HP:0000726
burning mouth syndrome	3	MONDO:0006687	EFO:1000850
cocaine dependence	2	MONDO:0005186	EFO:0002610
irritable bowel syndrome	2	MONDO:0005052	EFO:0000555
panic disorder	2	MONDO:0005383	EFO:0004262
opiate dependence	2	MONDO:0005530	EFO:0005611
alcohol abuse	2	MONDO:0002046	MONDO:0002046
Parkinson disease	2	MONDO:0005180	MONDO:0005180
bipolar disorder	2	MONDO:0004985	MONDO:0004985
acute coronary syndrome	1	MONDO:0005542	EFO:0005672
autism spectrum disorder	1	MONDO:0005258	EFO:0003756

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

Clinical trials

Total trials: 158.

Phase distribution

Phase	Trials
Not specified	48
PHASE4	41
PHASE1	20
PHASE2	19
PHASE3	16
PHASE2/PHASE3	6
EARLY_PHASE1	5
PHASE1/PHASE2	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT05004987	PHASE4	RECRUITING	Aβ Dynamics in LLMD
NCT05737511	PHASE4	NOT_YET_RECRUITING	Efficacy of Hydroxyzine for Patients With Panic Disorder
NCT00021528	PHASE4	COMPLETED	Sequenced Treatment Alternatives to Relieve Depression (STAR*D)
NCT00047671	PHASE4	COMPLETED	Ethnic Variations in Antidepressant Response
NCT00162916	PHASE4	UNKNOWN	Antidepressant Maintenance in Traumatic Brain Injury
NCT00221494	PHASE4	WITHDRAWN	Can Additional Drug Therapy Accelerate Response Time to Antidepressants
NCT00254007	PHASE4	COMPLETED	Depression and Traumatic Brain Injury
NCT00254020	PHASE4	COMPLETED	The Role of Cytokine-Serotonin Interactions in Post-Stroke Depression
NCT00376051	PHASE4	COMPLETED	Serotonergic Function and Behavioural and Psychological Symptoms of Frontotemporal Dementia
NCT00433121	PHASE4	COMPLETED	Discontinuation of Antipsychotics and Antidepressants Among Patients With BPSD
NCT00594269	PHASE4	COMPLETED	Dementia Antipsychotics And Antidepressants Discontinuation Study
NCT00602290	PHASE4	COMPLETED	Effectiveness of Methylphenidate in Improving Cognition and Function in Older Adults With Depression
NCT00666757	PHASE4	COMPLETED	A Study Comparing Duloxetine to Other Antidepressants in the Treatment of Severe Depression
NCT00825825	PHASE4	COMPLETED	Brain Effects of Escitalopram and Citalopram Using fMRI
NCT00834834	PHASE4	COMPLETED	Comparing Treatments for Self-Injury and Suicidal Behavior in People With Borderline Personality Disorder
NCT00893256	PHASE4	COMPLETED	Effect of Add-on Citalopram to Risperidone on Negative Symptoms in Schizophrenia
NCT00955474	PHASE4	TERMINATED	Seroquel Alone Versus Seroquel With an SSRI for Depression With Psychotic Symptoms
NCT01032083	PHASE4	COMPLETED	Antidepressant Controlled Trial for Negative Symptoms in Schizophrenia
NCT01041274	PHASE4	COMPLETED	DECIFER: Depression and Citalopram In First Episode Recovery
NCT01099592	PHASE4	TERMINATED	Antidepressants to Promote Recovery of Cardiac Patients Suffering From Depression
NCT01300364	PHASE4	UNKNOWN	Reboxetine and Citalopram as an Adjunct Treatment to Second Generation Antipsychotics in the Treatment of Negative Symptoms of Schizophrenia
NCT01436643	PHASE4	TERMINATED	Combination of Antidepressants and Fingolimod Relapsing-remitting Multiple Sclerosis (RRMS) Patients With Depression
NCT01473381	PHASE4	COMPLETED	Safety and Efficacy of Vilazodone in Major Depressive Disorder
NCT01557946	PHASE4	COMPLETED	Glutamatergic and GABAergic Mediators of Antidepressant Response in Major Depression
NCT01658228	PHASE4	COMPLETED	Combination Treatment Study for Memory Impairment and Depression
NCT01716221	PHASE4	COMPLETED	An Objective Double-blind Evaluation of Bupropion and Citalopram in an Individual With Friedreich Ataxia
NCT01764867	PHASE4	UNKNOWN	Algorithm Guided Treatment Strategies for Major Depressive Disorder
NCT01919216	PHASE4	COMPLETED	Placebo Effects in the Treatment of Depression: Cognitive and Neural Mechanisms
NCT02022709	PHASE4	COMPLETED	Efficacy of Exposure and Response Prevention(ERP) and SSRIs in Chinese OCD Patients
NCT02028026	PHASE4	WITHDRAWN	The Effects of Vilazodone on Glutamate in the Anterior Cingulate Cortex in Anxious Unipolar Depressives
NCT02237937	PHASE4	UNKNOWN	Optimizing Antidepressant Treatment by Genotype-dependent Adjustment of Medication According to the ABCB1 Gene
NCT02386475	PHASE4	COMPLETED	Effect of Serotonin and Levodopa in Ischemic Stroke
NCT02473250	PHASE4	COMPLETED	Prediction of Clinical Response to SSRI Treatment in Bipolar Disorder Using Serotonin 1A Receptor PET Imaging
NCT02711215	PHASE4	UNKNOWN	Patient Stratification and Treatment Response Prediction in Neuropharmacotherapy Using Hybrid Positron Emmission Tomography/Magnetic Resconance Imaging (PET/MR)
NCT02825342	PHASE4	TERMINATED	PPI’s and SSRI’s Therapy for the Management of NCCP
NCT03278938	PHASE4	WITHDRAWN	Add-on to Cognitive, Event-Related Potentials (ERP) and Electroencephalogram (EEG) Asymmetry in Affective Disorders
NCT03499171	PHASE4	UNKNOWN	Citalopram for Reflux Hypersensitivity and Functional Heartburn
NCT03746691	PHASE4	COMPLETED	Effect of Citalopram on Reflux Episodes in Healthy Volunteers
NCT03779789	PHASE4	COMPLETED	Vortioxetine in the Elderly vs. Selective Serotonin Reuptake Inhibitors (SSRIs): a Pragmatic Assessment
NCT04975724	PHASE4	UNKNOWN	Safety of Liposom With Citalopram in Elderly Patients With Major Depressive Disorder

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (5) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of DPWG Guideline for citalopram and CYP2C19	DPWG	CYP2C19	yes	yes
Annotation of CPIC Guideline for citalopram, escitalopram and CYP2C19	CPIC	CYP2C19	yes	yes
Annotation of DPWG Guideline for citalopram, escitalopram and CYP2D6	DPWG	CYP2D6
Annotation of CPIC Guideline for citalopram, escitalopram and HTR2A	CPIC	HTR2A
Annotation of CPIC Guideline for citalopram, desvenlafaxine, duloxetin	CPIC	SLC6A4

PharmGKB also curates 63 clinical and 219 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.

441 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
CRIZOTINIB	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
OLODATEROL	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
TADALAFIL	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
TAFENOQUINE	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
UMECLIDINIUM	ChEMBL + PubChem	Phase 4 (approved)	SLC6A4
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	SLC6A4
ACRIVASTINE	ChEMBL	Phase 4 (approved)	SLC6A4
ALECTINIB	ChEMBL	Phase 4 (approved)	SLC6A4
ALLOPURINOL	ChEMBL	Phase 4 (approved)	SLC6A4
AMBENONIUM	ChEMBL	Phase 4 (approved)	SLC6A4
AMIODARONE	ChEMBL	Phase 4 (approved)	SLC6A4
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	SLC6A4
AMOXAPINE	ChEMBL	Phase 4 (approved)	SLC6A4
AMPHOTERICIN B	ChEMBL	Phase 4 (approved)	SLC6A4
APOMORPHINE	ChEMBL	Phase 4 (approved)	SLC6A4
ARFORMOTEROL	ChEMBL	Phase 4 (approved)	SLC6A4
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	SLC6A4
ASENAPINE	ChEMBL	Phase 4 (approved)	SLC6A4
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	SLC6A4
ATOMOXETINE	ChEMBL	Phase 4 (approved)	SLC6A4
ATRACURIUM	ChEMBL	Phase 4 (approved)	SLC6A4
AZATHIOPRINE	ChEMBL	Phase 4 (approved)	SLC6A4
AZELASTINE	ChEMBL	Phase 4 (approved)	SLC6A4
BALSALAZIDE	ChEMBL	Phase 4 (approved)	SLC6A4
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	SLC6A4
BENFLUOREX	ChEMBL	Phase 4 (approved)	SLC6A4
BENZPHETAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
BENZTROPINE	ChEMBL	Phase 4 (approved)	SLC6A4
BENZYDAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
BEPRIDIL	ChEMBL	Phase 4 (approved)	SLC6A4
BOSUTINIB	ChEMBL	Phase 4 (approved)	SLC6A4
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	SLC6A4
BROMHEXINE	ChEMBL	Phase 4 (approved)	SLC6A4
BROMODIPHENHYDRAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
BROMPERIDOL	ChEMBL	Phase 4 (approved)	SLC6A4
BROMPHENIRAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
BUPROPION	ChEMBL	Phase 4 (approved)	SLC6A4
BUTENAFINE	ChEMBL	Phase 4 (approved)	SLC6A4
CABERGOLINE	ChEMBL	Phase 4 (approved)	SLC6A4
CALCIPOTRIENE	ChEMBL	Phase 4 (approved)	SLC6A4
CALCITRIOL	ChEMBL	Phase 4 (approved)	SLC6A4
CANAGLIFLOZIN	ChEMBL	Phase 4 (approved)	SLC6A4
CARBINOXAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
CARIPRAZINE	ChEMBL	Phase 4 (approved)	SLC6A4
CARVEDILOL	ChEMBL	Phase 4 (approved)	SLC6A4
CEFONICID	ChEMBL	Phase 4 (approved)	SLC6A4
CELECOXIB	ChEMBL	Phase 4 (approved)	SLC6A4
CETIRIZINE	ChEMBL	Phase 4 (approved)	SLC6A4
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	SLC6A4
CHLORPHENIRAMINE	ChEMBL	Phase 4 (approved)	SLC6A4
CHLORPHENTERMINE	ChEMBL	Phase 4 (approved)	SLC6A4
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	SLC6A4
CHLORPROTHIXENE	ChEMBL	Phase 4 (approved)	SLC6A4
CINACALCET	ChEMBL	Phase 4 (approved)	SLC6A4
CINNARIZINE	ChEMBL	Phase 4 (approved)	SLC6A4
CISAPRIDE	ChEMBL	Phase 4 (approved)	SLC6A4
CLEMASTINE	ChEMBL	Phase 4 (approved)	SLC6A4
CLIDINIUM	ChEMBL	Phase 4 (approved)	SLC6A4
CLOBUTINOL	ChEMBL	Phase 4 (approved)	SLC6A4