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Citalopram
Citalopram
Synonyms None notable
Brand names Celapram, Celexa, Celica, Ciazil, Cipramil, Citalo, Talam and others
IUPAC name

IUPAC name
1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
ChemSpider

2669

DrugBank

DB00215

PubChem

2771

PDB fields

N/A

Formula

C20H21FN2O

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
InChIKey
InChIKey
WSEQXVZVJXJVFP-UHFFFAOYSA-N
SMILES
SMILES
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
(Jmol 3D structure)
Mol. mass

324.3919 g/mol

Citalopram is selective serotonin reuptake inhibitor (SSRI) likely favoured over other SSRIs in the treatment of cocaine dependence, mostly due to its relative lack of drug interactions, when compared to other SSRIs, combined with its low cost when compared to its S-enantiomer, escitalopram (due to patent protection). It was also used in the Sequenced Treatment Alternatives to Relieve Depression (STAR*D) trial, for this very same reason, that is, because it lacks significant drug interactions besides that due to its serotonergic mechanism of action. Although it is more dangerous in overdose than the other SSRIs and is the only one, aside from escitalopram, that is known to prolong the QT interval.[1]

It is worth noting, however, that a recent meta-analysis has found that neither citalopram, nor desipramine, show significant efficacy in the treatment of cocaine dependence.[2]

Chemical structuresEdit

Citalopram racemate
(R)-citalopram
Escitalopram
250px (R)-citalopram
250px Escitalopram


External linksEdit

Reference listEdit

  1. Penberthy, JK; Ait-Daoud, N; Vaughan, M; Fanning, T (March 2010). "Review of treatment for cocaine dependence." (PDF). Current Drug Abuse Reviews 3 (1): 49–62. doi:10.2174/1874473711003010049. PMID 20088819.
  2. Pani, PP; Trogu, E; Vecchi, S; Amato, L (December 2011). "Antidepressants for cocaine dependence and problematic cocaine use.". The Cochrane Database of Systematic Reviews (12): CD002950. doi:10.1002/14651858.CD002950.pub3. PMID 22161371.

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