Citalopram

Citalopram

(R)-(−)-citalopram (top), (S)-(+)-citalopram (bottom)
Clinical data
Pronunciation	/saɪˈtæləˌpræm, sɪ-/;
Trade names	Celexa, Cipramil, others (see below)
AHFS/Drugs.com	Monograph
MedlinePlus	a699001
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N06AB04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	80% peak at 4 h
Metabolism	Liver (CYP3A4 and CYP2C19)
Metabolites	Desmethylcitalopram (DCT) and didesmethylcitalopram (DDCT)
Biological half-life	35 h
Excretion	Mostly as unmetabolized citalopram, partly DCT and traces of DDCT in urine
Identifiers
IUPAC name (RS)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number	59729-33-8 Y
PubChem (CID)	2771
IUPHAR/BPS	7547
DrugBank	DB00215 Y
ChemSpider	2669 Y
UNII	0DHU5B8D6V Y
KEGG	D07704 Y
ChEBI	CHEBI:3723 Y
ChEMBL	CHEMBL549 Y
ECHA InfoCard	100.056.247
Chemical and physical data
Formula	C20H21FN2O
Molar mass	324.392 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
InChI 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

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, 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.

In the National Institute for Health and Clinical Excellence ranking of 10 antidepressants for efficacy and cost-effectiveness citalopram is fifth in effectiveness (after mirtazapine, escitalopram, venlafaxine, and sertraline) and fourth in cost-effectiveness. The ranking results were based on the meta-analysis by Andrea Cipriani. In another analysis by Cipriani, citalopram turned out to be more efficacious than paroxetine and reboxetine and more acceptable than tricyclics, reboxetine, and venlafaxine, but it seemed to be less efficacious than escitalopram.

Evidence for effectiveness of citalopram for treating depression in children is uncertain.

Controversy exists regarding the efficacy of antidepressants in treating depression depending on its severity and duration, as discussed in Selective serotonin reuptake inhibitor.