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Encyclopedia > Citalopram
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 C20H21FN2O 
Mol. mass 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 in urine
Therapeutic considerations
Pregnancy cat.

? Image File history File links This is a lossless scalable vector image. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System containing Psychoanaleptics. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Distinguished from fluorene and fluorone. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... Cytochrome P450 2C19 (abbreviated CYP2C19), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a psychiatric medication taken to alleviate clinical depression or dysthymia (milder depression). ... This article does not cite any references or sources. ... On the Threshold of Eternity. ... A mood disorder is a condition whereby the prevailing emotional mood is distorted or inappropriate to the circumstances. ... Body dysmorphic disorder (BDD) is a mental disorder that involves a disturbed body image. ... what up?? Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components (Seligman, Walker & Rosenhan, 2001). ...


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™ , Citrol™, Seropram™ (Europe and Australia), Recital™ (Israel, Thrima Inc. for Unipharm Ltd.), Zetalo (India), Celepram™, Ciazil™ (Australia), Zentius™ (South America, Roemmers) and Cipram™ (Denmark, H. Lundbeck A/S). SSRI redirects here; for other uses, see SSRI (disambiguation). ... Forest Laboratories is a pharmaceutical company based in New York, New York, USA. It is Chaired by Howard Solomon, father of Novelist Andrew Solomon. ...

Contents

History

Citalopram was originally created in 1989[1] by the pharmaceutical company Lundbeck. The patent expired in 2003, allowing other companies legally to produce generic versions. H. Lundbeck A/S (also known as Lundbeck) is a Danish international pharmaceutical company engaged in the research and development, production, marketing and sale of drugs for the treatment of psychiatric and neurological disorders. ... For other uses, see Patent (disambiguation). ... A generic drug (pl. ...


Lundbeck has recently released an updated formulation called escitalopram (also known as Cipralex™ or Lexapro™), which is the S-enantiomer of the racemic citalopram (see below), and acquired a new patent for it. In the United States, Forest Laboratories licenses the rights for both Celexa and Lexapro from Lundbeck, which is based in Denmark. Lexapro pills Escitalopram (Lexapro, Cipralex, Sipralexa and Seroplex)[1] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ...


Indications

Approved

Citalopram is primarily used to treat the symptoms of depression but can also be prescribed for social anxiety disorder, panic disorder or obsessive-compulsive disorder. Also prescribed in Huntington's disease and premenstrual dysphoric disorder. On the Threshold of Eternity. ... Social anxiety is an experience of fear, apprehension or worry regarding social situations and being evaluated by others. ... Panic Disorder is a psychiatric condition characterized by reccurring panic attacks in combination with significant behavioral change or at least a month of ongoing worry about the implications or concern about having other attacks. ... Premenstrual dysphoric disorder (PMDD) is a severe form of premenstrual syndrome, afflicting 8% of all women. ...


Unapproved/Off-label/Investigational

Citalopram has been found to significantly reduce the symptoms of diabetic neuropathy[2] and premature ejaculation.[3] There is also evidence that citalopram may be effective in the treatment of post-stroke pathological crying.[4] Diabetic neuropathies are neuropathic disorders that are associated with diabetes mellitus. ... This article or section is in need of attention from an expert on the subject. ... Emotional lability or pseudobulbar affect is described in labile affect. ...


Dosage

Initially, 10 or 20mg once daily, in the morning or evening, with or without food. If response is inadequate, consider an increase to 40 mg/day in 20 mg increments at intervals of no less than 1 week. Some elderly patients may respond to 10 mg/day. Titrate to a maximum of 40 mg/day if needed and tolerated. Hepatic impairment: 30 mg/day (maximum dosage). If Celexa therapy is to be discontinued, taper the dose over 1-2 weeks.


Citalopram is formulated in 10, 20 and 40mg tablets.


Side effects and drug interactions

Citalopram is generally considered safe and well-tolerated in the therapeutic dose range of 20 to 60 mg/day. A doctor must always monitor a patient taking an SSRI like citalopram. 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.[5] This article does not cite any references or sources. ... SSRI is an acronym that stands for several things: It is a class of antidepressants called selective serotonin reuptake inhibitor SSRI also is used as the stock symbol for Silver Standard Resources Inc. ... Pharmacokinetics (in Greek: pharmacon meaning drug, and kinetikos meaning putting in motion) is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism. ... A drug interaction is a situation in which a substance affects the activity of a drug, i. ... In medicine and in psychiatry, comorbidity is either The presence of one or more disorders (or diseases) in addition to a primary disease or disorder; or The effect of such additional disorders or diseases. ...


Citalopram can have a number of adverse effects. In clinical trials, over 10% of patients reported one or more of the following side effects: fatigue, drowsiness, dry mouth, increased sweating (hyperhidrosis), trembling, headache, dizziness, sleep disturbances, insomnia, cardiac arrythmia, blood pressure changes, nausea/vomiting, diarrhea, heightened anorgasmia in females, impotence and ejaculatory problems in males. In rare cases (around over 1% of cases), some allergic reactions, convulsions, mood changes, anxiety and confusion have been reported. Also sedation may be present during treatment of citalopram. If this occurs it is advisable to take the dose at bedtime instead of in the morning. “Fatigue (physical)” redirects here. ... Somnolence (or drowsiness) is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods. ... Xerostomia is the medical term for a dry mouth due to a lack of saliva. ... Perspiration (also called sweating or sometimes transpiration) is the production and evaporation of a fluid, consisting primarily of water as well as a smaller amount of sodium chloride (the main constituent of table salt), that is excreted by the sweat glands in the skin of mammals. ... Primary hyperhidrosis is the condition characterized by abnormally increased perspiration, in excess of that required for regulation of body temperature. ... For the film see Tremors (film). ... A headache (cephalalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... // Pre-syncope is a sensation of feeling faint. ... A sleep disorder (somnipathy) is a disorder in the sleep patterns of a person or animal. ... This article is about the sleeping disorder. ... Cardiac arrhythmia is a group of conditions in which the muscle contraction of the heart is irregular or is faster or slower than normal. ... A sphygmomanometer, a device used for measuring arterial pressure. ... For other uses, see Nausea (disambiguation). ... Emesis redirects here. ... Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... Anorgasmia (also known as Retarded Ejaculation in males) is a form of sexual dysfunction, sometimes classified as a psychiatric disorder, where the patient cannot achieve orgasm, even with adequate stimulation. ... Erectile dysfunction (ED) or impotence is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis. ... Ejaculation is the ejecting of semen from the penis, and is usually accompanied by orgasm. ... An allergy is an abnormal, acquired sensitivity to a given substance, including pollen, drugs, or numerous environmental triggers. ... This article is about epileptic seizures. ... A mood swing is an extreme or rapid change in mood. ... what up?? Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components (Seligman, Walker & Rosenhan, 2001). ... Severe confusion of a degree considered pathological usually refers to loss of orientation (ability to place oneself correctly in the world by time, location, and personal identity), and often memory (ability to correctly recall previous events or learn new materal). ...


Another uncommon side effect is bruxism (teeth grinding).[6] When patients start using Citalopram they may experience a feeling similar to electricity or minor shocks in their upper body and in their hands. This is caused by the chemical changes occurring in the brain and they pass with time. Occasionally, panic attacks, thoughts of suicide or self-harm may occur or increase in the first few weeks, before the antidepressant effect starts.[7] Bruxism (from the Greek βρυγμός (brugmós), gnashing of teeth] is the grinding of the teeth, typically accompanied by the clenching of the jaw. ... Panic attacks are sudden, discrete periods of intense anxiety, fear and discomfort that are associated with a variety of somatic and cognitive symptoms[1]. The onset of these episodes is typically abrupt, and may have no obvious trigger. ... For other uses, see Suicide (disambiguation). ... Self-harm (SH) is deliberate injury to ones own body. ...


Citalopram and other SSRIs have been shown to cause sexual side effects in some patients, both males and females.[8] 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. Post SSRI Sexual Dysfunction (PSSD) is a type of sexual dysfunction caused by the previous use of SSRI antidepressants. ...


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.[9] In medicine, a contraindication is a condition or factor that increases the risk involved in using a particular drug, carrying out a medical procedure or engaging in a particular activity. ... This article does not cite any references or sources. ...


Discontinuation or withdrawal syndrome has been reported when treatment is stopped. Tapering off of Citalopram therapy, as opposed to abrupt discontinuation, is recommended in order to diminish the occurrence of discontinuation symptoms. SSRI discontinuation syndrome, also known as SSRI withdrawal syndrome or SSRI cessation syndrome, is a condition that can occur during or following the interruption, lowering of dose or discontinuation of regular SSRI or SNRI antidepressant drug usage. ...


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. A stereocenter in organic chemistry generally refers to a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to it. ... Some important fluorocarbons. ... The structure of the phenyl group In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 where the six carbon atoms are arranged in a cyclic ring structure. ... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ...

S-(+)-citalopram R-(−)-citalopram
S-(+)-citalopram R-(−)-citalopram
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 (hydrooxalate).[10] In both cases, the salt forms of the amine makes these otherwise lipophilic compounds water-soluble. Image File history File links Download high-resolution version (1100x1079, 174 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Escitalopram Citalopram ... Image File history File links Download high-resolution version (991x1100, 227 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Citalopram ... Image File history File links Download high-resolution version (1100x865, 20 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Citalopram ... Image File history File links Download high-resolution version (1100x865, 20 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Citalopram ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... H. Lundbeck A/S (also known as Lundbeck) is a Danish international pharmaceutical company engaged in the research and development, production, marketing and sale of drugs for the treatment of psychiatric and neurological disorders. ... Lexapro pills Escitalopram (Lexapro, Cipralex, Sipralexa and Seroplex)[1] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... It has been suggested that this article or section be merged into hydrogen bromide. ... An oxalate (called also: ethanedioate) is a salt or ester of oxalic acid. ... A magnified crystal of salt In chemistry, salt is a term used for ionic compounds composed of positively charged cations and negatively charged anions, so that the product is neutral and without a net charge. ... This article or section does not cite its references or sources. ...


References

  1. ^ Karin Dorell, M.D., Mary Ann Cohen, M.D., Shirish S. Huprikar, M.D., Jack M. Gorman, M.D., and Makeda Jones, M.D. (2005). "Citalopram-Induced Diplopia". Psychosomatics 46 (1): 91-93. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Andersen G., Vestergaard K., Riis JO. (1993). "Citalopram for post-stroke pathological crying.". Lancet(British edition) 342 (8875): 837-839. PMID 8104273. 
  5. ^ http://www.biopsychiatry.com/citalopram.html
  6. ^ Bruxism/Teeth grinding. Mayo Clinic (2007-05-18). Retrieved on 2007-07-25.
  7. ^ Citalopram Hydrobromide Brand name: Celexa Drug monograph; Contraindications. Internet Mental Health (August 1999). Retrieved on 2007-07-25.
  8. ^ Clayton A, Keller A, McGarvey EL. Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord 2006;91:27-32. PMID 16430968.
  9. ^ Citalopram Hydrobromide Brand name: Celexa Drug monograph; Symptoms and Treatment of Overdosage. Internet Mental Health (August 1999). Retrieved on 2007-07-25.]
  10. ^ Celexa.com

Main campus in downtown Rochester, Minnesota. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 206th day of the year (207th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 206th day of the year (207th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 206th day of the year (207th in leap years) in the Gregorian calendar. ...

External links

Pharmacological information and treatment study information:

Lunbeck's official websites for citalopram under the trade name Cipramil:

Forest's official websites for citalopram under the trade name Celexa:


  Results from FactBites:
 
Citalopram: Home (372 words)
Citalopram works by increasing the amount of serotonin, a natural substance in the brain that helps maintain mental balance.
Citalopram is also sometimes used to treat eating disorders, alcoholism, panic disorder, premenstrual dysphoric disorder, and social phobia.
Do not take citalopram if you are taking monoamine oxidase (MAO) inhibitors, including phenelzine (Nardil) and tranylcypromine (Parnate), or have stopped taking them within the past two weeks.
MedlinePlus Drug Information: Citalopram (1096 words)
Studies have shown that children and teenagers who take antidepressants ('mood elevators') such as citalopram may be more likely to think about harming or killing themselves or to plan or try to do so than children who do not take antidepressants.
If your child's doctor has prescribed citalopram for your child, you should watch his or her behavior very carefully, especially at the beginning of treatment and any time his or her dose is increased or decreased.
Citalopram is also sometimes used to treat eating disorders, alcoholism, panic disorder, premenstrual dysphoric disorder, and social phobia.
  More results at FactBites »

 

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