Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H21FN2O.BrH |
Molecular Weight | 405.304 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C3=CC=C(F)C=C3
InChI
InChIKey=WIHMBLDNRMIGDW-UHFFFAOYSA-N
InChI=1S/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
Citalopram (brand names: Celexa, Cipramil, and others) is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. It has U.S. Food and Drug Administration approval to treat major depression,[2]which it received in 1998, and is prescribed off-label for other conditions. In Australia, the UK, Germany, Portugal, Poland, and most European countries, it is licensed for depressive episodes and panic disorder with or without agoraphobia. In Spain, it is also used for obsessive-compulsive disorder. Citalopram HBr is a racemic bicyclic phthalane derivative designated (±)-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5carbonitrile, HBr. The mechanism of action of citalopram HBr as an antidepressant is presumed to be linked to potentiation of serotonergic activity in the central nervous system (CNS) resulting from its inhibition of CNS neuronal reuptake of serotonin (5-HT). In vitro and in vivo studies in animals suggest that citalopram is a highly selective serotonin reuptake inhibitor (SSRI) with minimal effects on norepinephrine (NE) and dopamine (DA) neuronal reuptake. The single-and multiple-dose pharmacokinetics of citalopram are linear and dose-proportional in a dose range of 10-60 mg/day. Biotransformation of citalopram is mainly hepatic, with a mean terminal half-life of about 35 hours.
Originator
Sources: https://lakemedelsverket.se/LMF/Lakemedelsinformation/?nplid=19980626000180Bigler, Allan J., et al. 'Quantitative structure-activity-relationships in a series of selective 5-HT uptake inhibitors.' EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 12.3 (1977): 289-295.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19616061 |
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Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23265880 |
0.78 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CELEXA Approved UseCitalopram HBr is indicated for the treatment of depression. The efficacy of citalopram HBr in the treatment of depression was established in 4 to 6 week, controlled trials of outpatients whose diagnosis corresponded most closely to the DSM-III and DSM-III-R category of major depressive disorder (see CLINICAL PHARMACOLOGY ). A major depressive episode (DSM-IV) implies a prominent and relatively persistent (nearly every day for at least 2 weeks) depressed or dysphoric mood that usually interferes with daily functioning, and includes at least five of the following nine symptoms: depressed mood, loss of interest in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt or suicidal ideation. The antidepressant action of citalopram HBr in hospitalized depressed patients has not been adequately studied. The efficacy of citalopram HBr in maintaining an antidepressant response for up to 24 weeks following 6 to 8 weeks of acute treatment was demonstrated in two placebo-controlled trials (see CLINICAL PHARMACOLOGY ). Nevertheless, the physician who elects to use citalopram HBr for extended periods should periodically re-evaluate the long-term usefulness of the drug for the individual patient. Launch Date1998 |
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Primary | Celexa Approved UseINDICATIONS AND USAGE. Celexa (citalopram HBr) is indicated for the treatment of depression. Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.2 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.5 ng/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.1 ng/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
21.7 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
43.7 ng/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
65.6 ng/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.6 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
204.5 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1153.2 ng × h/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
843.7 ng × h/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1010.4 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2070.3 ng × h/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2946.5 ng × h/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
533.2 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
77.5 h |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
79.3 h |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
38.5 h |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
40 h |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
39.5 h |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
36.3 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26% |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
26% |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
26% |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESMETHYLCITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
18% |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
18% |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
18% |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
18% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CITALOPRAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Other AEs: Dizziness, Drowsiness... Other AEs: Dizziness (mild, 1 patient) Sources: Drowsiness (mild, 1 patient) |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Disc. AE: Asthenia, Nausea... AEs leading to discontinuation/dose reduction: Asthenia (1%) Sources: Nausea (4%) Dry mouth (1%) Vomiting (1%) Dizziness (2%) Insomnia (3%) Somnolence (2%) Agitation (1%) |
760 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Other AEs: Seizures, Tachycardia... Other AEs: Seizures (1 patient) Sources: Tachycardia (1 patient) Neuromuscular disorders NEC (1 patient) Hyperthermia (severe, 1 patient) |
360 mg 1 times / day multiple, oral Highest studied dose Dose: 360 mg, 1 times / day Route: oral Route: multiple Dose: 360 mg, 1 times / day Sources: |
unhealthy, adult |
|
2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
Other AEs: Dizziness, Sweating... Other AEs: Dizziness (grade 5) Sources: Sweating Nausea Vomiting Tremor Somnolence Sinus tachycardia |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | mild, 1 patient | 800 mg single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Drowsiness | mild, 1 patient | 800 mg single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Agitation | 1% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Asthenia | 1% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Dry mouth | 1% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Vomiting | 1% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Dizziness | 2% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Somnolence | 2% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Insomnia | 3% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Nausea | 4% Disc. AE |
80 mg 1 times / day steady, oral (max) Studied dose Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, 18-66 years n = 1063 Health Status: unhealthy Condition: depression Age Group: 18-66 years Sex: M+F Population Size: 1063 Sources: |
Neuromuscular disorders NEC | 1 patient | 760 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Seizures | 1 patient | 760 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Tachycardia | 1 patient | 760 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Hyperthermia | severe, 1 patient | 760 mg single, oral Overdose |
unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: |
Nausea | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Sinus tachycardia | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Somnolence | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Sweating | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Tremor | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Vomiting | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
|
Dizziness | grade 5 | 2800 mg single, oral Overdose Dose: 2800 mg Route: oral Route: single Dose: 2800 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Citalopram and sexual side effects of selective serotonin reuptake inhibitors. | 1999 May |
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Citalopram and clozapine: potential drug interaction. | 2000 Apr |
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Antidepressant drugs appear to enhance cocaine-induced toxicity. | 2000 Feb |
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Near fatal case of atrio-ventricular block induced by amitriptyline at therapeutic dose. | 2000 Sep |
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Clinical significance of monitoring early symptom change to predict outcome. | 2001 |
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Involvement of 5-HT1A and 5-HT1B receptors for citalopram-induced hypothermia in the rat. | 2001 Apr |
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Are newer antidepressants really "better tolerated"? | 2001 Apr |
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S33005, a novel ligand at both serotonin and norepinephrine transporters: II. Behavioral profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine. | 2001 Aug |
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Reboxetine plus citalopram for refractory depression not responding to venlafaxine: possible mechanisms. | 2001 Feb |
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Disinhibition of libido: an adverse effect of SSRI? | 2001 Feb |
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The mood-lowering effect of tryptophan depletion: possible explanation for discrepant findings. | 2001 Feb |
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Too much hypothalamic serotonin transporter is bad for your mood. | 2001 Jan |
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Citalopram for OCD and Tourette's syndrome. | 2001 Jul |
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Involvement of adenosine in the effect of antidepressants on glutamate and aspartate release in the rat prefrontal cortex. | 2001 Jun |
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Pharmacological treatment of childhood obsessive-compulsive disorder: from theory to practice. | 2001 Mar |
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Effects of MDMA (ecstasy) on prepulse inhibition and habituation of startle in humans after pretreatment with citalopram, haloperidol, or ketanserin. | 2001 Mar |
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A comparison of citalopram and paroxetine in the treatment of panic disorder: a randomized, single-blind study. | 2001 May |
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Risk profile of SSrIs in elderly depressive patients with co-morbid physical illness. | 2001 May |
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Low-dose citalopram as a 5-HT neuroendocrine probe. | 2001 May |
|
Does mirtazapine have a more rapid onset than SSRIs? | 2001 May |
|
Trichotillomania associated with dementia: a case report. | 2001 May-Jun |
|
A retrospective study of citalopram in adolescents with depression. | 2001 Summer |
Sample Use Guides
Initial Treatment Celexa (citalopram HBr) should be administered at an initial dose of 20 mg once daily, with an increase to a maximum dose of 40 mg/day at an interval of no less than one week. Doses above 40 mg/day are not recommended due to the risk of QT prolongation. Additionally, the only study pertinent to dose response for effectiveness did not demonstrate an advantage for the 60 mg/day dose over the 40 mg/day dose. Special Populations 20 mg/day is the maximum recommended dose for patients who are greater than 60 years of age, patients with hepatic impairment, and for CYP2C19 poor metabolizers or those patients taking cimetidine or another CYP2C19 inhibitor.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27271269
It was investigated the mechanisms of cytotoxic effects of in vitro and in vivo citalopram treatment on liver and the following cytolethal events. For in vitro experiments, freshly isolated rat hepatocytes were exposed to citalopram along with/without various agents. In the in vitro experiments, citalopram (500 µM) exposure demonstrated cell death, a marked elevation in ROS formation, mitochondrial potential collapse, lysosomal membrane leakiness, glutathione (GSH) depletion and lipid peroxidation. In vivo biochemistry panel assays for liver enzymes function (AST, ALT and GGTP) and histological examination confirmed citalopram (20 mg/kg)-induced damage. Citalopram-induced oxidative stress cytotoxicity markers were significantly prevented by antioxidants, ROS scavengers, MPT pore sealing agents, endocytosis inhibitors, ATP generators and CYP inhibitors.
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C265
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C94725
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C28932
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KK-125
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ACTIVE MOIETY
SUBSTANCE RECORD