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Citalopram information


Citalopram
(R)-(−)-citalopram (top),
(S)-(+)-citalopram (bottom)
Clinical data
Pronunciation/sˈtæləˌpræm, sɪ-/;[1]
Trade namesCelexa, Cipramil, others[2]
AHFS/Drugs.comMonograph
MedlinePlusa699001
License data
  • US DailyMed: Citalopram
Pregnancy
category
  • AU: C[3]
Routes of
administration
oral, intravenous[4][5][6]
Drug classSelective serotonin reuptake inhibitor (SSRI)[7]
ATC code
  • N06AB04 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[9]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[8]Rx-only[10]
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
IUPAC name
  • (RS)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
  • 59729-33-8 checkY
PubChem CID
  • 2771
IUPHAR/BPS
  • 7547
DrugBank
  • DB00215 checkY
ChemSpider
  • 2669 checkY
UNII
  • 0DHU5B8D6V
KEGG
  • D07704 checkY
  • as salt: D00822 checkY
ChEBI
  • CHEBI:3723 checkY
ChEMBL
  • ChEMBL549 checkY
CompTox Dashboard (EPA)
  • DTXSID8022826 Edit this at Wikidata
ECHA InfoCard100.056.247 Edit this at Wikidata
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic 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 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 2021, it was the 31st most commonly prescribed medication in the United States, with more than 18 million prescriptions.[13][14]

  1. ^ "Citalopram". Merriam-Webster.com Dictionary.
  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 (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  12. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 361. ISBN 9780857113382.
  13. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  14. ^ "Citalopram Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Citalopram

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Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used...

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Escitalopram

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Escitalopram is the (S)-enantiomer of citalopram (which exists as a racemate), hence the name es-citalopram. Escitalopram was approved for medical use...

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Enantiomer

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escitalopram and citalopram. Citalopram is a racemate [1:1 mixture of (S)-citalopram and (R)-citalopram]; escitalopram [(S)-citalopram] is a pure enantiomer...

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Macropsia

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prescription drugs with side effects of macropsia deals with zolpidem and citalopram. Zolpidem is a drug prescribed for insomnia, and although it has proven...

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Venlafaxine

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respond to an SSRI were switched to either venlafaxine or another SSRI (citalopram); similar improvement was observed in both groups. Studies have not established...

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Reuptake

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kidney cells (HEK-SERT). They presented SERT with varying doses of either citalopram (an SSRI) or desipramine (an inhibitor of norepinephrine reuptake protein...

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The American Journal of Psychiatry

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Forest pleaded guilty to the charges of misbranding the drug Celexa (citalopram). The Complaint in Intervention clearly identifies a 2004 ghostwritten...

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Spontaneous orgasm

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psychotherapy, selective serotonin reuptake inhibitors (SSRIs) (e.g., paroxetine, citalopram, sertraline), the alpha-1 blocker silodosin, and anxiolytics. Medications...

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Pipamperone

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accelerate and enhance the antidepressant effect of citalopram (40 mg once daily), in a combination (citalopram/pipamperone) referred to as PipCit (code name...

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Pliva

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Food and Drug Administration to sell a generic version of Azithromycin, Citalopram, and Ondansetron. In October 2006, Barr Pharmaceuticals acquired Pliva...

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Death of Conrad Roy

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Like Carter, he had also been taking the antidepressant citalopram In the United States, citalopram carries a boxed warning stating it may increase suicidal...

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Didesmethylcitalopram

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antidepressant drug citalopram (racemic). Didesmethylescitalopram is an active metabolite of the antidepressant escitalopram, the S-enantiomer of citalopram. Like citalopram...

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Selective serotonin reuptake inhibitor

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and fluvoxamine were later approved for it as well. Escitalopram and citalopram are used off-label with acceptable efficacy, while fluoxetine is not considered...

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Desmethylcitalopram

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antidepressant drugs citalopram (racemic) and escitalopram (the S-enantiomer, which would be called desmethylescitalopram). Like citalopram and escitalopram...

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Ketamine

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reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine...

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Fluoxetine

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as an agonist of the σ1-receptor, with a potency greater than that of citalopram but less than that of fluvoxamine. However, the significance of this property...

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Antidepressants in Japan

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fluvoxamine, paroxetine, sertraline, and escitalopram; others such as citalopram and fluoxetine are either pending approval or no longer being considered...

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Lundbeck

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nervous system. In 1989, Lundbeck launched the antidepressant Celexa (citalopram), which became the cornerstone for the company's international expansion...

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MDMA

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moclobemide (Aurorix, Manerix). Serotonin reuptake inhibitors such as citalopram (Celexa), duloxetine (Cymbalta), fluoxetine (Prozac), and paroxetine (Paxil)...

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Allosteric serotonin reuptake inhibitor

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stereoisomer of the SSRI citalopram is included in this category. It is based on the observation that the R isomer of citalopram can decrease the potency...

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International nonproprietary name

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medications Celexa, Celapram and Citrol all contain the same active ingredient: citalopram; and the antibiotic widely known by the brand name Bactrim contains two...

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Cocaine

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reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine...

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Libido

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libido are fluoxetine (Prozac), paroxetine (Paxil), fluvoxamine (Luvox), citalopram (Celexa) and sertraline (Zoloft). Some antidepressant users have tried...

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Enantioselective synthesis

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S-(+)-carvone smells like caraway. Drug effectiveness: the antidepressant drug Citalopram is sold as a racemic mixture. However, studies have shown that only the...

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Development and discovery of SSRI drugs

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into a potent SSRI, called citalopram. But citalopram can also be viewed as a constrained analogue of paroxetine. Citalopram has the second most selectivity...

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Dapoxetine

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other SSRIs such as fluoxetine, paroxetine, sertraline, fluvoxamine, and citalopram have been used off-label to treat PE. Waldinger's meta-analysis shows...

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Methamphetamine

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(SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine...

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Serotonin reuptake inhibitor

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see other monoamine reuptake inhibitor pages such as SNRI and SNDRI. Citalopram (Celexa) Dapoxetine (Priligy) Escitalopram (Lexapro, Cipralex) Fluoxetine...

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