General
Preferred name
CITALOPRAM
Synonyms
CITALOPRAM HYDROBROMIDE ()
(+)-(S)-CITALOPRAM ()
(¡À)-Citalopram hydrobromide ()
escitalopram ()
Nitalapram HBr ()
Lu 10-171 ()
Citalopram HBr ()
Lu 10-171 HBr ()
Bonitrile HBr ()
(??)-Citalopram hydrobromide ()
Citalopram HBr ()
Citalopram derivative 1 ()
Citalopram (hydrobromide) ()
(±)-Citalopram hydrobromide ()
Nitalapram HBr, Prepram HBr, Bonitrile HBr, Lu 10-171 HBr ()
ESCITALOPRAM OXALATE ()
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile ()
Citalopram-d4 (hydrobromide) ()
LU-10-171-B ()
Paxoran ()
Celexa ()
Citalopram (as hydrobromide) ()
Cipramil ()
LU 10-171-B ()
NSC-758684 ()
Citadur ()
citalopram ()
Citalopram (hydrobromide) (CRM) ()
P&D ID
PD000475
CAS
59729-32-7
207559-01-1
59729-33-8
219861-08-2
1219803-58-3
Tags
available
probe
drug
Approved by
FDA
First approval
1998
Drug indication
Stroke
autism
Depression
Drug Status
approved
Max Phase
4.0
Probe info
Probe type
P&D approved
calculated probe
Probe selectivity
protein-selective
Probe sources
High-quality chemical probes
Probe Miner (suitable probes)
Probe targets
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Citalopram belongs to a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It has been found to relieve or manage symptoms of depression, anxiety, eating disorders and obsessive-compulsive disorder among other mood disorders. The antidepressant, anti-anxiety, and other actions of citalopram are linked to its inhibition of CNS central uptake of serotonin [FDA label]. Serotonergic abnormalities have been reported in patients with mood disorders. Behavioral and neuropsychological of effects of serotonin include the regulation of mood, perception, reward, anger, aggression, appetite, memory, sexuality, and attention, as examples. The onset of action for depression is approximately 1 to 4 weeks. The complete response may take 8-12 weeks after initiation of citalopram [L5224]. In vitro studies demonstrate that citalopram is a strong and selective inhibitor of neuronal serotonin reuptake and has weak effects on norepinephrine and dopamine central reuptake. The chronic administration of citalopram has been shown to downregulate central norepinephrine receptors, similar to other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase [A325].
ROE 12-23% of an oral dose of citalopram is found unchanged in the urine, while 10% of the dose is found in the faeces [FDA label].
MOA The mechanism of action of citalopram results from its inhibition of CNS neuronal reuptake of serotonin (5-HT) [FDA label]. The molecular target for citalopram is the serotonin transporter (solute carrier family 6 member 4, _SLC6A4_), inhibiting its serotonin reuptake in the synaptic cleft [A37688]. Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs [FDA label]. This drug has no or neglible affinity for _5-HT1A_, _5-HT2A_, _dopamine D_1 and _D2_, _α1-_, _α2_-, and_ β­ adrenergic_, _histamine H1_, _gamma-aminobutyric acid_ (GABA), _muscarinic_, _cholinergic_, and _benzodiazepine_ receptors. Antagonism of _muscarinic_, _histaminergic_, and _adrenergic receptors_ is thought to be associated with several anticholinergic, sedative, and cardiovascular effects of other psychotropic drugs [FDA label].
INDICATION For the treatment of depression, as indicated by the FDA label [FDA label]. Off-label indications include but are not limited to: treatment of sexual dysfunction, post-stroke behavioural changes, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy [FDA label], [A321], [A322], [A323], [A324], [A174406], [A174409], [A174412].
HALF-LIFE About 35 hours [FDA label].
TOXICITY **Oral (Human) LD**: 56 mg/kg **Intraperitoneal (Mouse) LD50**: 179 mg/kg **Acute toxicity** Symptoms of toxicity include dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. Rarely, symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and extremely rare cases of cardiac torsade de pointes) may occur. Acute renal failure has been a rare occurrence [A325]. In cases of overdose, establish and maintain the airway to ensure adequate ventilation and oxygen delivery. Due to the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are advised, in addition to supportive care. With the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit [FDA label]. **Pregnancy** This drug is categorized as pregnancy category C. In animal reproduction studies, citalopram has been shown to have adverse effects on embryo/fetal and postnatal development, which includes teratogenic effects when given at doses higher than human therapeutic doses. There are no sufficient and well-controlled studies in pregnant women; therefore, citalopram should be used during pregnancy only in cases where the potential benefit justifies the possible risk to the fetus [FDA label]. **Pregnancy-Nonteratogenic Effects** Neonates exposed to celexa and other SSRIs or SNRIs, late in the third trimester, have undergone complications requiring prolonged hospitalization, respiratory support, and parenteral feeding. Complications such as these can arise immediately upon delivery [FDA label]. **Nursing Mothers** Citalopram is excreted in human breast milk. There have been two reports of infants demonstrating high levels of somnolence, reduced feeding, and weight loss associated with breastfeeding from a mother taking citalopram. In one specific case, the infant was reported to recover completely after the discontinuation of citalopram. In the second case, no follow-up information was available for assessment. The decision whether to continue or discontinue either nursing or celexa should consider the risks of citalopram exposure for the infant versus the benefits of celexa treatment for the mother [FDA label].
METABOLISM Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, _demethylcitalopram_ by CYP2C19 and CYP3A4 [A174382]. Other metabolites include _didemethylcitalopram_ via CYP2D6 metabolism, and _citalopram N-oxide_ via monoamine oxidase enzymes and aldehyde oxidase. It is a deaminated propionic acid derivative [A174382]. After a single dose of citalopram, peak blood concentrations occur at approximately 4 hours [FDA label]. This drug in is found mainly unchanged in the plasma as citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be heavily involved in producing _demethylcitalopram_. Demethylcitalopram appears to be further N-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites exert little pharmacologic activity in comparison to the parent drug and are not likely to contribute to the clinical effect of citalopram [A325].
PHARMACODYNAMICS Citalopram belongs to a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It has been found to relieve or manage symptoms of depression, anxiety, eating disorders and obsessive-compulsive disorder among other mood disorders. The antidepressant, anti-anxiety, and other actions of citalopram are linked to its inhibition of CNS central uptake of serotonin [FDA label]. Serotonergic abnormalities have been reported in patients with mood disorders. Behavioral and neuropsychological of effects of serotonin include the regulation of mood, perception, reward, anger, aggression, appetite, memory, sexuality, and attention, as examples. The onset of action for depression is approximately 1 to 4 weeks. The complete response may take 8-12 weeks after initiation of citalopram [L5224].; ; In vitro studies demonstrate that citalopram is a strong and selective inhibitor of neuronal serotonin reuptake and has weak effects on norepinephrine and dopamine central reuptake. The chronic administration of citalopram has been shown to downregulate central norepinephrine receptors, similar to other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase [A325].
MOA The mechanism of action of citalopram results from its inhibition of CNS neuronal reuptake of serotonin (5-HT) [FDA label]. The molecular target for citalopram is the serotonin transporter (solute carrier family 6 member 4, _SLC6A4_), inhibiting its serotonin reuptake in the synaptic cleft [A37688].; ; Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs [FDA label]. This drug has no or neglible affinity for _5-HT1A_, _5-HT2A_, _dopamine D_1 and _D2_, _α1-_, _α2_-, and_ β­ adrenergic_, _histamine H1_, _gamma-aminobutyric acid_ (GABA), _muscarinic_, _cholinergic_, and _benzodiazepine_ receptors. Antagonism of _muscarinic_, _histaminergic_, and _adrenergic receptors_ is thought to be associated with several anticholinergic, sedative, and cardiovascular effects of other psychotropic drugs [FDA label].
TOXICITY **Oral (Human) LD**: 56 mg/kg; **Intraperitoneal (Mouse) LD50**: 179 mg/kg; ; **Acute toxicity**; ; Symptoms of toxicity include dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. Rarely, symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and extremely rare cases of cardiac torsade de pointes) may occur. Acute renal failure has been a rare occurrence [A325].; ; In cases of overdose, establish and maintain the airway to ensure adequate ventilation and oxygen delivery. Due to the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are advised, in addition to supportive care. With the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit [FDA label].; ; **Pregnancy**; ; This drug is categorized as pregnancy category C. In animal reproduction studies, citalopram has been shown to have adverse effects on embryo/fetal and postnatal development, which includes teratogenic effects when given at doses higher than human therapeutic doses. There are no sufficient and well-controlled studies in pregnant women; therefore, citalopram should be used during pregnancy only in cases where the potential benefit justifies the possible risk to the fetus [FDA label].; ; **Pregnancy-Nonteratogenic Effects**; ; Neonates exposed to celexa and other SSRIs or SNRIs, late in the third trimester, have undergone complications requiring prolonged hospitalization, respiratory support, and parenteral feeding. Complications such as these can arise immediately upon delivery [FDA label]. ; ; **Nursing Mothers**; ; Citalopram is excreted in human breast milk. There have been two reports of infants demonstrating high levels of somnolence, reduced feeding, and weight loss associated with breastfeeding from a mother taking citalopram. In one specific case, the infant was reported to recover completely after the discontinuation of citalopram. In the second case, no follow-up information was available for assessment. The decision whether to continue or discontinue either nursing or celexa should consider the risks of citalopram exposure for the infant versus the benefits of celexa treatment for the mother [FDA label].; ;
HALF-LIFE About 35 hours [FDA label]. ; ;
DESCRIPTION The marketed formulation is a racemic mixture of stereo-isomers. We show the non-isomeric molecule to represent this mixture. The S enantiomer is known as . R-citalopram has PubChem CID 6101829.
Marketed formulations may contain citalopram hydrobromide (PubChem CID 77995). (GtoPdb)
METABOLISM Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, _demethylcitalopram_ by CYP2C19 and CYP3A4 [A174382]. Other metabolites include _didemethylcitalopram_ via CYP2D6 metabolism, and _citalopram N-oxide_ via monoamine oxidase enzymes and aldehyde oxidase. It is a deaminated propionic acid derivative [A174382]. ; ; After a single dose of citalopram, peak blood concentrations occur at approximately 4 hours [FDA label]. This drug in is found mainly unchanged in the plasma as citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be heavily involved in producing _demethylcitalopram_. Demethylcitalopram appears to be further N-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites exert little pharmacologic activity in comparison to the parent drug and are not likely to contribute to the clinical effect of citalopram [A325].;
DESCRIPTION Citalopram is a racemate mixture of the active S(+)-enantiomer (Escitalopram; HY-14258) and R(-)-enantiomer. Citalopram is an orally active selective serotonin reuptake inhibitor (SSRI). Citalopram is an antidepressant and enhances serotoninergic neurotransmission[1][2][3].
PRICE 29
DESCRIPTION Citalopram (Lu 10-171 is an orally active, selective serotonin reuptake inhibitor (SSRI), a selective 5-hydroxytryptamine reuptake inhibitor, and a racemic mixture of the S(+)-enantiomer (Escitalopram) and the R(-)-enantiomer.Citalopram exhibits antidepressant activity and enhances serotonergic neurotransmission. It can be used to study Alzheimer's disease.
DESCRIPTION Citalopram hydrobromide is a selective serotonin reuptake inhibitor (SSRI). Citalopram hydrobromide inhibits 5-HT uptake into synaptosomes with an IC50 of 1.8 nM. Citalopram hydrobromideinhibits the 5-HT uptake in rabbit blood platelets with an IC50 of 14 nM. Antidepressant effect[1].
PRICE 33
DESCRIPTION DRUGMATRIX: Transporter Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) (TargetMol Bioactive Compound Library)
DESCRIPTION Sigma antagonist. Antipsychotic agent (Tocris Bioactive Compound Library)
DESCRIPTION Selective serotonin reuptake inhibitor (LOPAC library)
DESCRIPTION Highly potent and selective 5-HT uptake inhibitor (Tocriscreen Total)
DESCRIPTION Citalopram is a selective serotonin reuptake inhibitor (SSRI) used in the treatment of depression. (Enamine Bioactive Compounds)
DESCRIPTION Citalopram hydrobromide (XU-62-320) , a selective serotonin reuptake inhibitor (SSRI), selectively inhibits the CNS neuronal reuptake of serotonin, thereby potentiating serotonergic activity in the central nervous system (CNS). Citalopram hydrobromide is the orally bioavailable hydrobromide salt of the racemic bicyclic phthalene derivative citalopram with antidepressant activity. This agent has minimal effects on the CNS neuronal reuptake of norepinephrine (NE) and dopamine (DA). (TargetMol Bioactive Compound Library)
Cell lines
3
Organisms
1
Compound Sets
39
AdooQ Bioactive Compound Library
A10222
Axon Medchem Screening Library
1320
Cayman Chemical Bioactives
14572
23252
23253
22102
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL549
CHEMBL1200781
ChEMBL Drugs
CHEMBL549
CHEMBL1200781
Concise Guide to Pharmacology 2017/18
4621
7547
Concise Guide to Pharmacology 2019/20
4621
7547
Concise Guide to Pharmacology 2021/22
4621
7547
Concise Guide to Pharmacology 2023/24
4621
7547
CZ-OPENSCREEN Bioactive Library
DrugBank
DB00215
DrugBank Approved Drugs
DB00215
DrugCentral
663
DrugCentral Approved Drugs
663
DrugMAP
DM2G9AE
DMITX1G
DrugMAP Approved Drugs
DM2G9AE
DrugMatrix
Enamine Bioactive Compounds
EBC-12781
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS101224
Guide to Pharmacology
4621
7547
High-quality chemical probes
PD000475
Ki Database
CITALOPRAM
Escitalopram
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL549
CHEMBL1200781
Mcule NIBR MoA Box Subset
MCULE-1806848795
MedChem Express Bioactive Compound Library
HY-121203
HY-B1287
NCATS Inxight Approved Drugs
0DHU5B8D6V
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
Prestwick Chemical Library
Probe Miner (suitable probes)
P31645/1495162
ReFrame library
Selleckchem Bioactive Compound Library
citalopram-hbr
escitalopram-oxalate
TargetMol Bioactive Compound Library
H050-0003
T1483
The Spectrum Collection
Tocris Bioactive Compound Library
1427
Tocriscreen Total
External IDs
78
Properties
(calculated by RDKit )
Molecular Weight
324.16
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
0
Rotatable Bonds
5
Ring Count
3
Aromatic Ring Count
2
cLogP
3.81
TPSA
36.26
Fraction CSP3
0.35
Chiral centers
1.0
Largest ring
6.0
QED
0.84
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Serotonin Transporter
SSRI
5-HT Receptor,Serotonin Transporter
5-HT
Selectivity
Reuptake
MOA
serotonin transporter inhibitor
Inhibitor
5-HT Reuptake Inhibitors
Pathway
Autophagy
GPCR/G protein
Neuroscience
Neuronal Signaling
Primary Target
5-HT Transporters
Member status
member
Therapeutic Class
Antidepressants
Source data