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Sertraline

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Sertraline chemical structure
Sertraline

(1S)-cis-4-(3,4-dichlorophenyl)-
1,2,3,4-tetrahydro-
N-methyl-
1-naphthalenamine

IUPAC name
CAS number
79617-96-2
ATC code

N06AB06

PubChem
68617
DrugBank
APRD00175
Chemical formula {{{chemical_formula}}}
Molecular weight 342.7
Bioavailability 44%
Metabolism N-demethylation (liver)
Elimination half-life ~26 hours
Excretion Urine
Pregnancy category C
Legal status Rx-only
Routes of administration oral

Sertraline hydrochloride (also labeled under numerous brand names: Zoloft, Sertralin, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an orally administered antidepressant of the selective serotonin reuptake inhibitor (SSRI) type. It was first approved by the Food and Drug Administration (FDA) in 1991.

IndicationsEdit

ApprovedEdit

Sertraline is used medically mainly to treat the symptoms of depression and anxiety. It is also prescribed for the treatment of obsessive-compulsive disorder (OCD)[1], post-traumatic stress disorder (PTSD)[2], premenstrual dysphoric disorder (PMDD)[3], panic disorder (PD)[4] and social phobia/social anxiety disorder[5].

Unapproved, off-label, and investigationalEdit

Sertraline can also be used in the treatment of generalized anxiety disorder[6], binge eating disorder [7], and premature ejaculation[8].

There is also evidence that sertraline may be effective in the treatment of refractory neurocardiogenic syncope in children and adolescents[9].

A study has shown that sertraline is an effective treatment for impulsive aggressive behavior in personality disordered patients.[10]

Side effectsEdit

Sertraline can have adverse effects, including: Sleep disorder (both insomnia and increased sleep time) , asthenia, gastrointestinal complaints, tremors, confusion, dizziness, anorgasmia, nauseua/vomiting, and decreased libido; it can induce mania or hypomania in around 0.5% of patients. It has also been known to cause minor weight loss. It is contraindicated in individuals taking MAOIs or undergoing electroconvulsive therapy.

Until 2003, Zoloft was only approved for use in adults ages 18 and over; that year it was approved by the FDA for use in treating children ages 6 to 17 with extreme obsessive compulsive disorder. In June 2004, Britain banned Zoloft's use by minors and in February 2005, Pfizer was forced to change Zoloft's labeling to include information regarding increased incidences of suicidal behavior and depression in adolescent users of the drug. According to mentalhealth.com, Zoloft is not currently recommended or advised for use in individuals under the age of 18. After these changes, multiple incidences and at least one medical study showed an increased suicide risk in seniors who were taking Zoloft. In response to these findings, the FDA released a public health warning. This warning indicates that anyone currently using Zoloft for any reason has a greater chance of exhibiting suicidal thoughts or behaviors regardless of age. This warning is questionable, however, due to the types of illnesses Zoloft is used to treat, it is impossible to determine if these tendencies are a side effect of the drug or the illness the drug is meant to treat. The warning, however, claimed to do so, and claims to show that Zoloft can cause suicidal action or ideation where there was none.

Zoloft has long been seen as the best option for breastfeeding mothers who wish to continue breastfeeding and be able to take their antidepressants. Despite its apparent safety and effectiveness during the breastfeeding period, recent studies and consumer complaints have seen a need to alter Zoloft's labeling regarding use during the third trimester of pregnancy. Though there are no teratogenetic defects associated with Zoloft, there is reason to be concerned about its effects on infants who were exposed to sertraline during the third trimester in utero. It seems that Zoloft use in late pregnancy significantly increases the potential need for hospitalization and breathing assistance in the newborn period and has also been shown to cause an increased risk of neonatal death. In light of this increased risk it is still being used due to the greater potential risk of a seriously depressed mother to herself and her fetus. Like all other medications Zoloft's use must be decided only after carefully weighing out all potential risks and benefits.

FormulationsEdit

File:Zoloft logo.png
Zoloft logo

Sertraline is manufactured by Pfizer and sold as Zoloft in the United States as small green 25 mg tablets, blue 50 mg tablets, and yellow 100 mg tablets (Generic 100 mg sertraline tablets are also yellow), each of which is scored to allow easy halving.

In the UK, the brand name is Lustral and is available in white 50 mg or 100 mg scored tablets, according to the British National Formulary (BNF). Elsewhere in the EU the brand name is Zoloft, available in white 50 mg or 100 mg scored tablets. In Australia, only the 50 mg and 100 mg strengths are available, both as white tablets.

Sertraline is an odorless, white, sparingly soluble crystalline solid. The minimum effective dose is usually 50 mg per day (it can be still effective at 25 mg or 37.5 mg), but lower doses may be used in the initial weeks of treatment to acclimate the patient's body, especially the liver, to the drug and to minimize the severity of any side effects. Patients who do not experience relief of symptoms at 50 mg a day may have their dose increased, up to 200 mg a day.

The patent for this brand-name drug expired in June 2006.[11] The drug is now availible in generic form in the United States. The generic version of the drug is being produced by Israeli drug maker Teva Pharmaceutical Industries Ltd.[12] In Scandinavia a generic drug called Sertralin, manufactured by HEXAL is available. The price differences between Zoloft and Sertralin are as much as 1.50 dollars per pill.[How to reference and link to summary or text] In India, this drug is sold under the name Zosert.

PrecautionsEdit

  • Liver impairment can affect the elimination of this drug from the body. If someone with liver impairment is treated with sertraline, lower or less frequent dosage should be used.
  • Patients should limit their alcohol intake while on sertraline (or any antidepressant). Because the liver is doubly taxed with processing both substances (in addition to any other drugs the patient may be taking), alcohol remains in the bloodstream longer, so the effects of alcohol may be more strongly and quickly felt by people taking sertraline or other antidepressants.
  • According to some studies grapefruit juice might interfere with the metabolisation of sertraline, increasing its concentration in the blood.
  • People 80 years or older should be started on 25 mg initial dose.

DopamineEdit

Sertraline appears to also be a minor dopamine reuptake inhibitor. At higher dosages (300 mg/day), sertraline inhibits the reuptake of dopamine as well as serotonin.

ControversyEdit

In June 2003, Britain banned sertraline's use for patients under 18 years of age after studies showed a link to increasing suicidal rates. Similar concern has prevailed in the United States, where only the anti-depressant fluoxetine (another SSRI) was officially banned by the FDA for the treatment of depression in minors. However, because the antidepressant-suicide link is correlational, scientists do not know whether the increased suicide risk for people taking antidepressants occurs because the drugs make people suicidal, whether suicide occurs because the drugs un-depress the people enough to motivate the energy required to commit suicide (a popular theory), whether people statistically more likely to commit suicide are over-represented among takers of Zoloft, or because of a fourth, unknown factor.

The brand-name form of setraline, Zoloft, was widely advertised to consumers as "correcting a chemical imbalance", a claim not found in the FDA-approved product labeling. Hundreds of millions of dollars were spent promoting Zoloft this way while it was still on-patent. Some have argued that this advertising may lead consumers to believe that they must take Zoloft to recover when in fact they may benefit from other non-medical treatments such as psychotherapy or exercise.[13]

Discontinuation SyndromeEdit

Main article: SSRI discontinuation syndrome

Zoloft, along with other SSRIs, has been associated with a "cessation syndrome." This syndrome has both somatic and psychological elements, although SSRIs fall short of being classified as addictive. This non-addictive classification stems from the fact persons given the drug will not seek it out in ever-increasing quantities. Although Zoloft is defined as non-habit forming, the existence of SSRI discontinuation syndrome often necessitates a gradual tapering of one's prescribed dose when seeking to stop SSRI therapy. The prescription insert for Zoloft describes the potential side effects SSRI discontinuation as follows:

"During marketing of Zoloft and other SSRIs and SNRIs (Serotonin and Norepinephrine Reuptake Inhibitors), there have been spontaneous reports of adverse events occurring upon discontinuation of these drugs, particularly when abrupt, including the following: dysphoric mood, irritability, agitation, dizziness, sensory disturbances (e.g. paresthesias such as electric shock sensations), anxiety, confusion, headache, lethargy, emotional lability, insomnia, and hypomania. While these events are generally self-limiting, there have been reports of serious discontinuation symptoms."[14]

See alsoEdit

ReferencesEdit

  1. Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ. (1999). Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder.. Journal of Clinical Psychopharmacology 19 (2): 172-176. PMID 10211919.
  2. Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM. (2000). Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial.. The Journal of the American Medical Association 283 (14): 1837-1844. PMID 10770145.
  3. Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W. (1997). Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group.. The Journal of the American Medical Association 278 (12): 983-988. PMID 9307345.
  4. Londborg PD, Wolkow R, Smith WT, DuBoff E, England D, Ferguson J, Rosenthal M, Weise C. (1998). Sertraline in the treatment of panic disorder. A multi-site, double-blind, placebo-controlled, fixed-dose investigation.. The British Journal of Psychiatry 173: 54-60. PMID 9850204.
  5. Katzelnick DJ, Kobak KA, Greist JH, Jefferson JW, Mantle JM, Serlin RC. (1995). Sertraline for social phobia: a double-blind, placebo-controlled crossover study.. The American Journal of Psychiatry 152 (9): 1368-1371. PMID 7653696.
  6. Allgulander C, Dahl AA, Austin C, Morris PL, Sogaard JA, Fayyad R, Kutcher SP, Clary CM. (2004). Efficacy of sertraline in a 12-week trial for generalized anxiety disorder.. The American Journal of Psychiatry 161: 1642-1649. PMID 15337655.
  7. McElroy SL, Casuto LS, Nelson EB, Lake KA, Soutullo CA, Keck PE Jr, Hudson JI. (2000). Placebo-controlled trial of sertraline in the treatment of binge eating disorder.. The American Journal of Psychiatry 157 (6): 1004-1006. PMID 10831483.
  8. McMahon CG. (1998). Treatment of premature ejaculation with sertraline hydrochloride: a single-blind placebo controlled crossover study.. The Journal of Urology 159 (6): 1935-1938. PMID 9598491.
  9. Grubb BP, Samoil D, Kosinski D, Kip K, Brewster P. (1994). Use of sertraline hydrochloride in the treatment of refractory neurocardiogenic syncope in children and adolescents.. Journal of the American College of Cardiology 24 (2): 490-494. PMID 8034887.
  10. Kavoussi RJ, Liu J, Coccaro EF. (1994). An open trial of sertraline in patients with personality disorder who also have impulsive aggression.. Journal of Clinical Psychiatry 55 (4): 137-141. PMID 8071257.
  11. http://money.cnn.com/2006/07/17/news/companies/pfizer/index.htm
  12. http://www.tevapharm.com/pr/2006/pr_626.asp
  13. Lacasse, J.R. & Leo, J. (2005). "Serotonin and Depression: A Disconnect Between the Advertisements and Scientific Literature". PLos Medicine, 2(12), e392.
  14. http://www.zoloft.com/pdf/ZoloftUSPI.pdf/

External linksEdit



Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine


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