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Statements

Subject Item
n2:DB00215
rdf:type
n3:Drug
n3:description
Citalopram hydrobromide belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Citalopram and its N-demethylated metabolites exist as a racemic mixture but its effects are largely due to the S-enantiomer, S-citalopram and S-demthylcitalopram. Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize &alpha;- or &beta;-adrenergic, dopamine D<sub>2</sub> or histamine H<sub>1</sub> receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT<sub>1A</sub> and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT<sub>1A</sub> and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Citalopram is approved for treatment of depression. Unlabeled indications include mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy. Citalopram has the fewest drug-drug interactions of the SSRIs.
n3:dosage
n29:271B5E3C-363D-11E5-9242-09173F13E4C5 n29:271B5E3D-363D-11E5-9242-09173F13E4C5 n29:271B5E3E-363D-11E5-9242-09173F13E4C5 n29:271B5E3F-363D-11E5-9242-09173F13E4C5 n29:271B5E3A-363D-11E5-9242-09173F13E4C5 n29:271B5E3B-363D-11E5-9242-09173F13E4C5 n29:271B5E40-363D-11E5-9242-09173F13E4C5 n29:271B5E41-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. Clin Pharmacol Ther. 1992 Nov;52(5):547-52. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1424428 # Atmaca M, Kuloglu M, Tezcan E, Semercioz A: The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. Int J Impot Res. 2002 Dec;14(6):502-5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12494286 # Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8104273 # Clayton A, Keller A, McGarvey EL: Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord. 2006 Mar;91(1):27-32. Epub 2006 Jan 20. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16430968 # Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8732438 # FDA label # Hyttel J, Bogeso KP, Perregaard J, Sanchez C: The pharmacological effect of citalopram residues in the (S)-(+)-enantiomer. J Neural Transm Gen Sect. 1992;88(2):157-60. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1632943 # Caccia S: Metabolism of the newer antidepressants. An overview of the pharmacological and pharmacokinetic implications. Clin Pharmacokinet. 1998 Apr;34(4):281-302. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9571301
n3:group
approved
n3:halfLife
35 hours
n3:indication
For the treatment of depression. Unlabeled indications include: treatment of mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy.
n3:manufacturer
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owl:sameAs
n13:DB00215 n22:DB00215
dcterms:title
Citalopram
adms:identifier
n18:2771 n19:46508746 n20:0378-6231-01 n21:PA449015 n23:3723 n24:2669 n25:25870 n26:C07572 n27:D07704 n28:DB00215 n30:Citalopram
n3:mechanismOfAction
The antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT<sub>1A</sub> autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
n3:packager
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n3:patent
n10:2049368 n10:2353693
n3:routeOfElimination
12-23% of an oral dose of citalopram is recovered unchanged in the urine, while 10% of the dose is recovered in the feces.
n3:synonym
Nitalapram Citadur
n3:toxicity
Symptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.
n3:volumeOfDistribution
* 12 L/kg Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, demethylcitalopram does not cross the barrier well.
n8:hasAHFSCode
n32:28-16-04-20
n3:foodInteraction
Take without regard to meals. Avoid St.John's Wort. Avoid alcohol.
n3:proteinBinding
Citalopram, dimethylcitalopram, and didemethylcitalopram is 80% bound to plasma proteins.
n3:salt
n3:synthesisReference
Hans Petersen, "Method for the preparation of citalopram." U.S. Patent US6229026, issued December, 1992.
n6:hasConcept
n7:M0023529
foaf:page
n15:citalo.htm n16:citalopram.html
n3:IUPAC-Name
n4:271B5E46-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5E4C-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5E4B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5E48-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5E49-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5E4A-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5E44-363D-11E5-9242-09173F13E4C5 n4:271B5E5B-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5E42-363D-11E5-9242-09173F13E4C5 n4:271B5E45-363D-11E5-9242-09173F13E4C5 n4:271B5E5D-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5E43-363D-11E5-9242-09173F13E4C5
n8:hasATCCode
n9:N06AB04
n3:H-Bond-Acceptor-Count
n4:271B5E52-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5E53-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5E4D-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5E4E-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5E50-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5E4F-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5E51-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
59729-33-8
n3:category
n3:clearance
The systemic clearance of citalopram was 330 mL/min, with approximately 20% of that due to renal clearance.
n3:containedIn
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n4:271B5E47-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5E54-363D-11E5-9242-09173F13E4C5