| Candidate ID: | R0082 |
| Source ID: | DB00215 |
| Source Type: | approved |
| Compound Type: |
small molecule
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| Compound Name: |
Citalopram
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| Synonyms: |
Citalopram; Nitalapram
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| Molecular Formula: |
C20H21FN2O
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| SMILES: |
CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
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| Structure: |
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| DrugBank Description: |
Citalopram belongs to a class of antidepressant agents known as selective _serotonin-reuptake inhibitors_ (SSRIs) and is widely used to treat the symptoms of depression. Its chemical structure is unrelated to that of other SSRIs or of tricyclic, tetracyclic, or other prescribed antidepressants . Citalopram is also known as _Celexa_, and available in tablet and solution forms . This drug was initially approved by the FDA in 1998 .
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| CAS Number: |
59729-33-8
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| Molecular Weight: |
324.3919
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| DrugBank Indication: |
For the treatment of depression, as indicated by the 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 , , , , , , , .
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| DrugBank Pharmacology: |
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 . 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 .
<i>In vitro</i> 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 .
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| DrugBank MoA: |
The mechanism of action of citalopram results from its inhibition of CNS neuronal reuptake of serotonin (5-HT) . The molecular target for citalopram is the serotonin transporter (solute carrier family 6 member 4, _SLC6A4_), inhibiting its serotonin reuptake in the synaptic cleft .
Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs . 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 .
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| Targets: |
Sodium-dependent serotonin transporter inhibitor; Histamine H1 receptor binder
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| Inclusion Criteria: |
Indication associated
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