Citalopram

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Citalopram

Citalopram is an antidepressant

Antidepressant

An antidepressant is a psychiatric medication used for alleviating major depressive disorder or dysthymia. Drug groups known as MAOIs, tricyclics, and second-generation antidepressants such as SSRIs, and serotonin-norepinephrine reuptake inhibitors are particularly associated with the term....
drug

Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
used to treat major depression associated with mood disorder

Mood disorder

A mood disorder is the term given for a group of diagnoses in the Diagnostic and Statistical Manual of Mental Disorders classification system where a disturbance in the person's Mood is hypothesised to be the main underlying feature....
s. It is also used on occasion in the treatment of body dysmorphic disorder

Body dysmorphic disorder

Body dysmorphic disorder is a mental disorder in which the affected person is excessively concerned about and preoccupied by an imagined or minor defect in their Body image....
and anxiety

Anxiety

Anxiety is a psychological and physiological state characterized by cognitive, somatic, emotional, and behavioral components. These components combine to create an unpleasant feeling that is typically associated with uneasiness, fear, or worry....
.

Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitor

Selective serotonin reuptake inhibitor

Selective serotonin reuptake inhibitors or serotonin-specific reuptake inhibitor are a class of antidepressants used in the treatment of Clinical depression, anxiety disorders, and some personality disorders....
s (SSRIs). It is sold under the brand-names Celexa (U.S. and Canada, Forest Laboratories, Inc.

Forest Laboratories

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Encyclopedia

Citalopram is an antidepressant

Antidepressant

Medication

Mood disorder

Body dysmorphic disorder

Body dysmorphic disorder is a mental disorder in which the affected person is excessively concerned about and preoccupied by an imagined or minor defect in their Body image....
and anxiety

Anxiety

Selective serotonin reuptake inhibitor

Forest Laboratories

Forest Laboratories is a pharmaceutical company headquartered in New York City, USA. Its revenues for the year ended 31 March 2007 were US$3.4 billion....
), Cipramil (Australia, Brazil, Finland, Germany, Ireland, Sweden, United Kingdom), Citrol, Seropram, Talam (Europe and Australia), Citabax, Citaxin (Poland), Citalec (Slovakia), Recital (Israel, Thrima Inc. for Unipharm Ltd.), Zetalo (India), Celapram, Ciazil (Australia, New Zealand), Zentius (South America, Roemmers), Ciprapine (Ireland), Cilift (South Africa), Citox (Mexico),Citopam , Akarin (Denmark, Nycomed), and Cipram (Denmark, H. Lundbeck A/S).

History

Citalopram (si-'tal-?-?pram) was originally created in 1989, by the pharmaceutical company Lundbeck

Lundbeck

H. Lundbeck A/S is a Denmark international pharmaceutical company engaged in the research and development, production, marketing and sale of medication for the psychotherapy of Psychiatry and Neurology mental illnesss....
. The patent

Patent

A patent is a set of exclusive rights granted by a state to an inventor or his assignee for a term of patent in exchange for a disclosure of an invention....
expired in 2003, allowing other companies to legally produce generic

Generic drug

A generic drug is a medication which isproduced and distributed without patent protection. The generic drug may still have a patent on the formulation but not on the active ingredient....
versions.

Lundbeck has recently released an updated formulation called escitalopram

Escitalopram

Escitalopram is the pure enantiomer of racemic citalopram and is a selective serotonin reuptake inhibitor . Escitalopram is used in the treatment of Major depressive disorder and anxiety....
(also known as Cipralex or Lexapro), which is the S-enantiomer

Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
of the racemic

Racemic

In chemistry, a racemic mixture, or racemate, is one that has equal Amount of substance of left- and right-handed enantiomer of a Chirality molecule....
citalopram (see below

Citalopram

Citalopram is an antidepressant Medication used to treat Major depressive disorder associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety....
), 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.

Indications

Approved

Citalopram is used to treat the symptoms of major depression, social anxiety disorder and panic disorder

Panic disorder

Panic Disorder is an anxiety disorder characterized by recurring severe panic attacks. It may also include significant behavioral change lasting at least a month and of ongoing worry about the implications or concern about having other attacks....
.

Citalopram is a Pgp

P-glycoprotein

P-glycoprotein is a well-characterized ABC-transporter of the Multidrug_resistance/Transporter_associated_with_antigen_processing subfamily. P-gp is also called ABCB1, ATP-binding cassette sub-family B member 1, MDR1, and PGY1....
substrate and is actively transported by that protein from the brain. The efficacy of citalopram in people possessing a certain version of Pgp (genetic TT-allele) is likely to be diminished. This suggests that in non-responders to citalopram a switch to antidepressant which is not a Pgp substrate, such as fluoxetine

Fluoxetine

Fluoxetine hydrochloride is an antidepressant of the selective serotonin reuptake inhibitor class. Fluoxetine is approved for the treatment of major depressive disorder , obsessive-compulsive disorder , bulimia nervosa, anorexia nervosa, panic disorder and premenstrual dysphoric disorder....
(Prozac, Fontex) or mirtazapine

Mirtazapine

Mirtazapine is an antidepressant introduced by Organon International in 1994 used for the treatment of moderate to severe clinical depression....
(Remeron)—but not to venlafaxine

Venlafaxine

Venlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class first introduced by Wyeth in 1993. It is prescribed for the treatment of major depressive disorder and anxiety disorders, among other uses....
(Effexor), amitriptyline

Amitriptyline

Amitriptyline hydrochloride is a tricyclic antidepressant Medication. It is a white, odorless, crystalline compound which is freely soluble in water; it is usually dispensed in tablet form....
(Elavil) or paroxetine

Paroxetine

Paroxetine is a selective serotonin reuptake inhibitor antidepressant. It was released in 1992 by the pharmaceutical company GlaxoSmithKline. It is used to treat major depressive disorder, obsessive-compulsive disorder, panic disorder and social phobia disorders in adult Patient#Outpatient vs inpatient....
(Paxil), which are Pgp substrates—may be beneficial.

Unapproved, Off-label and Investigational

Citalopram has been found to significantly reduce the symptoms of diabetic neuropathy

Diabetic neuropathy

Diabetic neuropathies are neuropathy disorders that are associated with diabetes mellitus. These conditions are thought to result from diabetic microvascular disease involving small blood vessels that supply nerves ....
, and premature ejaculation

Premature ejaculation

Premature ejaculation , also known as rapid ejaculation, rapid climax, premature climax or early ejaculation , is a condition affecting 25%-40% of men in the U.S....
. There is also evidence that citalopram may be effective in the treatment of post-stroke pathological crying

Labile affect

Labile affect or pseudobulbar affect refers to the pathological expression of laughter, crying, or smile. It is also known as emotional lability, pathological laughter and crying, emotional incontinence, or, more recently, involuntary emotional expression disorder ....
.

While on its own Citalopram is less effective than amitriptyline

Amitriptyline

Side effects and drug interactions

Citalopram is generally considered safe and well-tolerated in the therapeutic dose

Effective dose

An effective dose in pharmacology is the amount of medication that produces a therapeutic response in 50% of the people taking it, sometimes also called ED-50....
range of 20 to 60 mg/day. A doctor must always monitor a patient taking an SSRI

Selective serotonin reuptake inhibitor

Selective serotonin reuptake inhibitors or serotonin-specific reuptake inhibitor are a class of antidepressants used in the treatment of Clinical depression, anxiety disorders, and some personality disorders....
like citalopram. Distinct from some other agents in its class, citalopram exhibits linear pharmacokinetics

Pharmacokinetics

Pharmacokinetics is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism....
and minimal drug interaction

Drug interaction

A drug interaction is a situation in which a substance affects the activity of a medication, i.e. the effects are increased or decreased, or they produce a new effect that neither produces on its own....
potential, making it a better choice for the elderly or comorbid

Comorbidity

In medicine, comorbidity is either:* The presence of one or more disorders in addition to a primary disease or disorder; or* The effect of such additional disorders or diseases....
patients.

Citalopram should be taken with caution when using St John's wort

St John's wort

St John's wort used alone refers to the species Hypericum perforatum, also known as Tipton's Weed or Klamath weed, but, with qualifiers, is used to refer to any species of the genus Hypericum....
, as resulting drug interactions could be adverse. This may be caused by compounds in the plant extract reducing the efficacy of the hepatic

Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
cytochrome P enzymes that process citalopram. It has also been suggested that such compounds, including hypericin

Hypericin

Hypericin is a red-coloured anthraquinone-derivative, which is together with Hyperforin one of the principal active constituents of Hypericum . Hypericin is believed to act as an antibiotic and non-specific kinase Enzyme inhibitor....
, hyperforin

Hyperforin

Hyperforin is one of the principal constituents identified in St John's wort....
and flavonoids, could have SSRI-mimetic effects on the nervous system, although this is still subject to debate. One study found that Hypericum

Hypericum

Hypericum is a genus of about 400 species of flowering plants in the family Clusiaceae, subfamily Hypericoideae . The genus has a nearly world-wide distribution, missing only from tropical lowlands, deserts and polar regions....
extracts had similar effects in treating moderate depression as citalopram, with fewer side effects.

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

Somnolence

Somnolence is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods . It has two distinct meanings, referring both to the usual state preceding falling asleep, and the chronic condition referring to being in that state independent of a circadian rhythm....
, dry mouth

Xerostomia

Xerostomia is the medical term for a dry mouth due to a lack of saliva. Xerostomia is sometimes colloquially called pasties, cottonmouth, or doughmouth....
, increased sweating (hyperhidrosis

Hyperhidrosis

Hyperhidrosis is the condition characterized by abnormally increased perspiration, in excess of that required for regulation of body temperature....
), trembling

Tremor

Tremor is an unintentional, somewhat rhythmic, muscle movement involving to-and-fro movements of one or more body parts. It is the most common of all involuntary movements and can affect the hands, arms, head, face, vocal cords, trunk, and legs....
, headache

Headache

In medicine a headache or wiktionary:cephalalgia is a symptom of a number of different conditions of the head and sometimes neck. Some of the causes are benign while others are medical emergencies....
, dizziness

Dizziness

Dizziness describes a number of subjective symptoms, which the patient may describe as feelings of lightheadedness, floating, wooziness, giddiness, confusion, disorientation or loss of balance....
, sleep disturbances

Sleep disorder

A sleep disorder is a medical disorder of the sleep patterns of a person or animal. Some sleep disorders are serious enough to interfere with normal physical, mental and emotional functioning....
, insomnia

Insomnia

Insomnia is a symptom of a sleep disorder characterized by persistent difficulty falling sleep or staying asleep despite the opportunity. Insomnia is a symptom, not a stand-alone diagnosis or a disease....
, cardiac arrhythmia

Cardiac arrhythmia

Cardiac arrhythmia is a term for any of a large and heterogeneous group of conditions in which there is abnormal Electrical conduction system of the heart in the heart....
, hallucinations, blood pressure

Blood pressure

Blood pressure is the pressure exerted by circulating blood on the walls of blood vessels, and constitutes one of the principal vital signs. The pressure of the circulating blood decreases as it moves away from the heart through artery and capillary, and toward the heart through veins....
changes, nausea

Nausea

Nausea is the sensation of unease and discomfort in the stomach with an urge to vomit....
and/or vomiting

Vomiting

Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Undesired vomiting may result from many causes, ranging from gastritis or poisoning to brain tumors, or elevated intracranial pressure....
, diarrhea

Diarrhea

In medicine, diarrhea, also spelled diarrhoea , is characterized by frequent loose or liquid bowel movements. The spelling of "diarrhea" is an appropriation of the Greek "diarrhoia" meaning "a flowing through." ....
, heightened anorgasmia

Anorgasmia

Anorgasmia is a form of sexual dysfunction sometimes classified as a psychiatric disorder in which the patient cannot achieve orgasm, even with "adequate" stimulation....
in females, impotence

Erectile dysfunction

Erectile dysfunction is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis sufficient for satisfactory sexual performance....
and ejaculatory

Ejaculation

Ejaculation is the ejecting of semen from the penis, and is usually accompanied by orgasm. It is usually the result of sexual stimulation. Rarely, it is due to prostatic disease....
problems in males. In rare cases (around over 1% of cases), some allergic reactions

Allergy

Allergy is a Disorder of the immune system often also referred to as atopy. Allergic reactions occur to Natural environmental substances known as allergens; these reactions are Acquired disorder, predictable and rapid....
, convulsions

Seizure

An epileptic seizure is a transient symptom of abnormal, excessive or synchronous neuronal activity in the brain. It can manifest as an alteration in mental state, tonic or clonic movements, convulsions, and various other psychic symptoms ....
, mood swing

Mood swing

A mood swing is an extreme or rapid change in Emotional mood. They are commonly associated with mood disorders, of which the classic example is bipolar disorder and also a major factor in hyperactive or hyperactive/inattentive ADHD....
s, anxiety

Anxiety

Mental confusion

Confusion, of a pathological degree, usually refers to loss of orientation and often memory . Confusion as such is not synonymous with inability to focus attention, although severe inability to focus attention can cause, or greatly contribute to, 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.

One rare side effect of antidepressant medications is bruxism

Bruxism

Bruxism is the grinding of the teeth, and is typically accompanied by the clenching of the jaw. It is an oral Parafunctional habit that occurs in most humans at some time in their lives....
(teeth grinding). However there is no evidence directly implicating Citalopram with teeth grinding.

When taken with Prilosec, the clearance of Citalopram may be reduced, leading to higher blood levels of Citalopram. Prilosec inhibits the CYP450 2C19 enzyme, one of the two primary enzymes responsible for the metabolism of Citalopram. Dosage adjustments may be needed due to this effect.

Citalopram and other SSRIs have been shown to cause a preoccupation with sexual content in some patients, both males and females.

Citalopram is contraindicated

Contraindication

In medicine, a contraindication is a condition or factor that increases the risks involved in using a particular medication, carrying out a medical procedure, or engaging in a particular activity....
in individuals taking MAOIs

Monoamine oxidase inhibitor

Monoamine oxidase inhibitors are a class of powerful Antidepressants prescribed for the treatment of clinical depression. They are particularly effective in treating atypical depression, and have also shown efficacy in smoking cessation....
. The drug considered relatively safe in overdose, although fatal cases of dosages 840 mg to 1960 mg have been reported.

SSRI discontinuation syndrome

SSRI discontinuation syndrome

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

Stereochemistry

Citalopram has one stereocenter

Stereocenter

A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
, to which a 4-fluoro

Fluorocarbon

Fluorocarbons, sometimes referred to as perfluorocarbons, are organofluorine compounds that contain only carbon and fluorine bonded together in strong carbon?fluorine bonds....
phenyl group

Phenyl group

In organic chemistry, the phenyl group or phenyl ring is the functional group with the formulawhere the six carbon atoms are arranged in a cyclic ring structure....
and an N,N-dimethyl-3-aminopropyl group bind. Due to this chirality

Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
the molecule exists in (two) enantiomer

Enantiomer



*S-(+)-citalopram*	R-(-)-citalopram

Citalopram is sold as a racemic

Racemic

In chemistry, a racemic mixture, or racemate, is one that has equal Amount of substance of left- and right-handed enantiomer of a Chirality molecule....
mixture, consisting of 50% R-(-)-citalopram and 50% S-(+)-citalopram. Only the S-(+) enantiomer has the desired antidepressant effect. Lundbeck

Lundbeck

Escitalopram

Escitalopram is the pure enantiomer of racemic citalopram and is a selective serotonin reuptake inhibitor . Escitalopram is used in the treatment of Major depressive disorder and anxiety....
. Whereas citalopram is supplied as the hydrobromide

Hydrobromic acid

Hydrobromic acid is a strong acid acid formed by dissolving the diatomic molecule hydrogen bromide in water. It has a Acid dissociation constant of −9, making it a stronger acid than hydrochloric acid, but not as strong as hydrogen iodide....
, escitalopram is sold as the oxalate

Oxalate

An oxalate is the deprotonated, charged form of oxalic acid or an ester of oxalic acid. As a salt, the oxalate anion has the chemical formula C2O42- or 22-....
salt (hydrooxalate). In both cases, the salt forms of the amine makes these otherwise lipophilic

Lipophilic

Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene....
compounds water-soluble.

External links

Cipramil Patient Information Leaflet