Citalopram
From Wikipedia, the free encyclopedia
| Image:Citalopram-skeletal.png | |
| Citalopram
| |
| Systematic (IUPAC) name | |
| 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)- 1,3-dihydroisobenzofuran-5-carbonitrile | |
| Identifiers | |
| CAS number | 59729-33-8 |
| ATC code | N06AB04 N06AB10 |
| PubChem | 2771 |
| DrugBank | APRD00147 |
| Chemical data | |
| Formula | C20H21N2FO |
| Mol. weight | 324.392 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 80% |
| Metabolism | hepatic (CYP3A4 & CYP2C19) |
| Half life | 35 hours |
| Excretion | Mostly as unmetabolized Citalopram, partly DCT and traces of DDCT |
| Therapeutic considerations | |
| Pregnancy cat. |
C |
| Legal status |
℞ Prescription only |
| Routes | Oral |
Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety.
Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). It is sold under the brand-names Celexa™ (U.S., Forest Laboratories, Inc.), Cipramil™ , Seropram™ (Europe and Australia), Celepram™ and Ciazil™ (Australia).
Contents |
[edit] History
Citalopram was originally created by the pharmaceutical company Lundbeck and the patent for it expired in 2003, allowing other companies legally to produce generic versions.
Lundbeck has recently released an updated formulation called escitalopram oxalate (also known as Cipralex™ or Lexapro™), which is simply the S-enantiomer of the racemic citalopram (see below), and acquired a new patent for it.
[edit] Indications
[edit] Approved
Citalopram is primarily used to treat the symptoms of depression but can also be prescribed for panic disorder or obsessive- compulsive disorders.
[edit] Unapproved/Off-label/Investigational
Citalopram has been found to significantly reduce the symptoms of diabetic neuropathy<ref>Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF. (1992). "The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy.". Clinical Pharmacology & Therapeutics 52 (5): 547-552. PMID 1424428.</ref> and premature ejaculation.<ref>Atmaca M, Kuloglu M, Tezcan E, Semercioz A. (2002). "The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study.". International Journal of Impotence Research 14 (6): 502-505. PMID 12494286.</ref> There is also evidence that citalopram may be effective in the treatment of post-stroke pathological crying.<ref>Andersen G., Vestergaard K., Riis JO. (1993). "Citalopram for post-stroke pathological crying.". Lancet(British edition) 342 (8875): 837-839. PMID 8104273.</ref>
[edit] Side effects and drug interactions
Citalopram is safe and well-tolerated in the therapeutic dose range of 20 to 60 mg/day. Distinct from some other agents in its class, Citalopram exhibits linear pharmacokinetics and minimal drug interaction potential, making it a better choice for the elderly or comorbid patients.<ref name=http://www.biopsychiatry.com/citalopram.html>http://www.biopsychiatry.com/citalopram.html</ref>
Citalopram can have a number of adverse effects. In clinical trials, over 10% of patients reported fatigue, drowsiness, dry mouth, increased sweating (hyperhidrosis), trembling, headache, dizziness, sleep disturbances, cardiac arrythmia, blood pressure, nausea/vomiting, diarrhea, heightened anorgasmia in females, impotence and ejaculatory problems. In rare cases (around over 1% of cases), some allergic reactions, convulsions, mood changes, anxiety and confusion have been reported. Occasionally, panic attacks, thoughts of suicide or self-harm may occur or increase in the first few weeks, before the antidepressant effect starts.<ref name=http://www.mentalhealth.com/drug/p30-c04.html#Head_5>http://www.mentalhealth.com/drug/p30-c04.html#Head_5</ref>
Citalopram and other SSRIs have been shown to cause sexual side effects in most patients, both males and females<ref>Clayton A, Keller A, McGarvey EL. Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord 2006;91:27-32. PMID 16430968.</ref>. Although usually reversible, these sexual side effects can sometimes last for months, years or possibly indefinitely even after the drug has been completely withdrawn. This disorder is known as Post SSRI Sexual Dysfunction.
Citalopram is contraindicated in individuals taking MAOIs. It is considered relatively safe in overdose, although fatal cases of dosages 840 mg to 1960 mg have been reported.<ref name=http://www.mentalhealth.com/drug/p30-c04.html#Head_12 >http://www.mentalhealth.com/drug/p30-c04.html#Head_12</ref>
[edit] Stereochemistry
Citalopram has a stereocenter, to which a 4-fluorophenyl group and an N,N-dimethyl-3-aminopropyl group bind. Due to this chirality the molecule exists in (two) enantiomeric forms (mirror images). They are termed S-(+)-citalopram and R-(−)-citalopram.
| Image:S-(+)-citalopram-3D-sticks.png | Image:R-(−)-citalopram-3D-sticks.png |
| Image:S-(+)-citalopram.png | Image:R-(-)-citalopram.png |
| S-(+)-citalopram | R-(−)-citalopram |
Citalopram is sold as a racemic mixture, consisting of 50% R-(−)-citalopram and 50% S-(+)-citalopram. Only the S-(+) enantiomer has the desired antidepressant effect. Lundbeck now markets the S-(+) enantiomer, the generic name of which is escitalopram. Whereas citalopram is supplied as the hydrobromide, escitalopram is sold as the oxalate salt.<ref name=Celexa.com>Celexa.com</ref> The salt form makes these otherwise lipophilic compounds watersoluble.
[edit] External links
Pharmacological information and treatment study information:
- http://www.biopsychiatry.com/citalopram.html
- Celexa / Citalopram Fact Sheet
- FDA patient fact sheet on Citalopram hydrobromide
Lunbeck's official websites for citalopram under the trade name Cipramil:
Forest's official websites for citalopram under the trade name Celexa:
- Cipramil Patient Information Leaflet Cipramil Patient Information Leaflet
- Link page to external chemical sources.
[edit] References
<references/>
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