Citalopram

This article is about the racemic form of the drug. For its (S)-enantiomer, see Escitalopram.

Citalopram
(R)-(−)-citalopram (top),
(S)-(+)-citalopram (bottom)
Clinical data
Pronunciation/saɪˈtæləˌpræm, sɪ-/;[1]
Trade namesCelexa, Cipramil, others[2]
AHFS/Drugs.comMonograph
MedlinePlusa699001
License data
Pregnancy
category
Dependence
liability		Low
Addiction
liability		Low
Routes of
administration		oral, intravenous[4][5][6]
Drug classSelective serotonin reuptake inhibitor (SSRI)[7]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80%
peak at 4 hours[7]
Protein binding<80%[10]
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 Edit this at Wikidata
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • 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 checkY
  • Key:WSEQXVZVJXJVFP-UHFFFAOYSA-N checkY
  (verify)

Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class.[7][10] It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia.[7] The antidepressant effects may take one to four weeks to occur.[7] It is typically taken orally (swallowed by mouth).[7][10] 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.[4] It has also been used intravenously in other parts of the world in some other circumstances.[5][6]

Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating.[7] Serious side effects include an increased risk of suicide in those under the age of 25, serotonin syndrome, glaucoma, and QT prolongation.[7] It should not be used in persons who take or have recently taken an MAO inhibitor.[7] There are concerns that use during pregnancy may harm the fetus.[3]

Citalopram was approved for medical use in the United States in 1998.[7] It is on the World Health Organization's List of Essential Medicines.[11] It is available as a generic medication.[12] In 2022, it was the 40th most commonly prescribed medication in the United States, with more than 15 million prescriptions.[13][14]

  1. ^ "Citalopram". Merriam-Webster.com Dictionary. Merriam-Webster.
  2. ^ Cite error: The named reference Citalopram International was invoked but never defined (see the help page).
  3. ^ a b "Citalopram (Celexa) Use During Pregnancy". Drugs.com. Retrieved 23 December 2018.
  4. ^ a b Kasper S, Müller-Spahn F (June 2002). "Intravenous antidepressant treatment: focus on citalopram". European Archives of Psychiatry and Clinical Neuroscience. 252 (3): 105–109. doi:10.1007/s00406-002-0363-8. PMID 12192466. S2CID 24991131.
  5. ^ a b Cite error: The named reference ivocd was invoked but never defined (see the help page).
  6. ^ a b Altamura AC, Dell'Osso B, Buoli M, Zanoni S, Mundo E (August 2008). "Intravenous augmentative citalopram versus clomipramine in partial/nonresponder depressed patients: a short-term, low dose, randomized, placebo-controlled study". J Clin Psychopharmacol. 28 (4): 406–410. doi:10.1097/JCP.0b013e31817d5931. PMID 18626267. S2CID 25013120. Retrieved 12 August 2023.
  7. ^ a b c d e f g h i j "Citalopram Hydrobromide Monograph for Professionals". Drugs.com. AHFS. Retrieved 23 December 2018.
  8. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  9. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  10. ^ a b c d "Celexa- citalopram tablet, film coated". DailyMed. 15 August 2019. Retrieved 28 October 2020.
  11. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  12. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 361. ISBN 9780857113382.
  13. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  14. ^ "Citalopram Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.