Citalopram

Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia. The antidepressant effects may take one to four weeks to occur. It is typically taken orally (swallowed by mouth). In some European countries, it is sometimes given intravenously (injected into a vein) to initiate treatment, before switching to the oral route of administration for continuation of treatment. It has also been used intravenously in other parts of the world in some other circumstances.

Citalopram
(R)-(−)-citalopram (top),
(S)-(+)-citalopram (bottom)
Clinical data
Pronunciation/sˈtæləˌpræm, sɪ-/;
Trade namesCelexa, Cipramil, others
AHFS/Drugs.comMonograph
MedlinePlusa699001
License data
Pregnancy
category
  • AU: C
Routes of
administration
oral, intravenous
Drug classSelective serotonin reuptake inhibitor (SSRI)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
Pharmacokinetic data
Bioavailability80%
peak at 4 hours
Protein binding<80%
MetabolismLiver (CYP3A4 and CYP2C19)
MetabolitesDesmethylcitalopram (DCT) and didesmethylcitalopram (DDCT)
Elimination half-life35 hours
ExcretionMostly as unmetabolized citalopram, partly DCT and traces of DDCT in urine
Identifiers
  • (RS)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.056.247
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
  • InChI=1S/C20H21FN2O/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 Y
  • Key:WSEQXVZVJXJVFP-UHFFFAOYSA-N Y
  (verify)

Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating. Serious side effects include an increased risk of suicide in those under the age of 25, serotonin syndrome, glaucoma, and QT prolongation. It should not be used in persons who take or have recently taken an MAO inhibitor. There are concerns that use during pregnancy may harm the fetus.

Citalopram was approved for medical use in the United States in 1998. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 31st most commonly prescribed medication in the United States, with more than 18 million prescriptions.

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