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Sertraline

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Sertraline
Clinical data
Pronunciation/ˈsɜːrtrəˌliːn/
Trade namesZoloft, Lustral, Setrona, others[1]
AHFS/DrugsMonograph
MedlinePlusa697048
License data
Pregnancy
category
Addiction
liability		None[3]
Routes of
administration		By mouth
Drug classSelective serotonin reuptake inhibitor(SSRI)
ATC code
Legal status
Legal status
  • AU:S4(Prescription only)
  • BR:Class C1(Other controlled substances)[4]
  • CA:℞-only
  • NZ:Prescription only
  • UK:POM(Prescription only)
  • US:℞-only
  • In general: ℞ (Prescription only)
Pharmacokineticdata
Bioavailability44%[citation needed]
Protein binding98.5%[citation needed]
MetabolismLiver(primarilyN-demethylationmainly byCYP2B6;also metabolism byCYP2C19,others)[5][9]
Metabolites•Desmethylsertraline
• Others (e.g.,hydroxylatedmetabolites,glucuronideconjugates)[5]
Eliminationhalf-life• Sertraline: 26 hours (32 hours in females, 22 hours in males; range 13–45 hours)[5][6][7][8]
• Desmethylsertraline: 62–104 hours[5]
ExcretionUrine(40–45%)[5]
Feces(40–45%)[5]
Identifiers
  • (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H17Cl2N
Molar mass306.23g·mol−1
3D model (JSmol)
  • ClC1=CC=C([C@H]2C3=C([C@H](CC2)NC)C=CC=C3)C=C1Cl
  • InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1checkY
  • Key:VGKDLMBJGBXTGI-SJCJKPOMSA-NcheckY
(verify)

Sertraline,sold under the brand nameZoloftamong others, is anantidepressantof theselective serotonin reuptake inhibitor(SSRI) class.[10]Theeffectivenessof sertraline fordepressionis similar to that of other antidepressants, and the differences are mostly confined toside effects.Sertraline is better tolerated than the oldertricyclic antidepressants.Sertraline is effective forpanic disorder,social anxiety disorder,generalized anxiety disorder(GAD), andobsessive–compulsive disorder(OCD). Although approved forpost-traumatic stress disorder(PTSD), sertraline leads to only modest improvement in this condition.[11][12]Sertraline also alleviates the symptoms ofpremenstrual dysphoric disorder(PMDD) and can be used in sub-therapeutic doses or intermittently (luteal phase dosing) for its treatment.[13]

Sertraline shares the common side effects andcontraindicationsof other SSRIs, with high rates ofdiarrhea,nausea,insomnia,andsexual dysfunction,but it appears not to lead to muchweight gain,and its effects oncognitive performanceare mild. Similar to other antidepressants, the use of sertraline for depression may be associated with a mildly elevated rate ofsuicidal thoughtsin people under the age of 25 years old. It should not be used together withmonoamine oxidase inhibitors(MAOIs): this combination may causeserotonin syndrome,which can be life-threatening in some cases. Sertraline taken during pregnancy is associated with an increase incongenital heart defectsin newborns.[14][15]

Sertraline was invented and developed by scientists atPfizerand approved for medical use in the United States in 1991. It is on theWorld Health Organization's List of Essential Medicines.[16]It is available as ageneric medication.[10]In 2016, sertraline was the most commonly prescribed psychotropic medication in the United States.[17]In 2021, it was the eleventh most commonly prescribed medication in the United States, with over 39million prescriptions.[18][19]

Medical uses

[edit]

Sertraline has been approved formajor depressive disorder(MDD),obsessive–compulsive disorder(OCD),post-traumatic stress disorder(PTSD),premenstrual dysphoric disorder(PMDD),panic disorder,andsocial anxiety disorder(SAD). Sertraline is approved for use in children with OCD.[20]

Depression

[edit]

Inmeta-analyses,sertraline displays similar efficacy to other SSRI antidepressants, with anodds ratiofor response in clinical depression of between 1.44 and 1.67.[21][22]However, as with other antidepressants, the nature and clinical significance of this effect remain disputed.[23][24]A major study of sertraline in a broad primary care population found improvements in general mental health, quality of life, and anxiety.[25]However, it failed to find significant effects on depression in either the mildly or severely depressed, and the clinical relevance and accuracy of the positive effects found have been questioned.[26][27]

In severaldouble-blindstudies, sertraline was consistently more effective thanplacebofordysthymia,a more chronic variety of depression, and comparable toimipraminein that respect. Sertraline also improves the functional impairments of dysthymia to a similar degree whether group Cognitive-Behavioural Therapy is undergone or not.[28]

Limited pediatric data also demonstrates reduction in depressive symptoms in the pediatric population though remains a second line therapy after fluoxetine.[29][30]

Comparison with other antidepressants

[edit]

In general, sertraline efficacy is similar to that of other antidepressants.[31]For example, a meta-analysis of 12 new-generation antidepressants showed that sertraline andescitalopramare the best in terms of efficacy and acceptability in the acute-phase treatment of adults with depression.[32]Comparative clinical trials demonstrated that sertraline is similar in efficacy against depression tomoclobemide,[33]nefazodone,[34]escitalopram,bupropion,[35]citalopram,fluvoxamine,paroxetine,[32]venlafaxine,[36]andmirtazapine.[37]Sertraline may be more efficacious for the treatment of depression in the acute phase (first four weeks) thanfluoxetine.[38]

There are differences between sertraline and some other antidepressants in their efficacy in the treatment of different subtypes of depression and in their adverse effects. For severe depression, sertraline is as good asclomipraminebut is better tolerated.[36]Sertraline appears to work better inmelancholic depressionthan fluoxetine,paroxetine,andmianserinand is similar to thetricyclic antidepressantssuch asamitriptylineandclomipramine.[31]In the treatment of depression accompanied byOCD,sertraline performs significantly better thandesipramineon the measures of both OCD and depression.[28][39]Sertraline is equivalent to imipramine for the treatment of depression with co-morbid panic disorder, but it is better tolerated.[40]Compared with amitriptyline, sertraline offered a greater overall improvement inquality of lifeof depressed patients.[31]

Depression in elderly

[edit]

Sertraline used for the treatment of depression in elderly (older than 60) patients is superior to placebo and comparable to another SSRI fluoxetine, andtricyclic antidepressants(TCAs) amitriptyline,nortriptylineandimipramine.Sertraline has much lower rates of adverse effects than these TCAs, with the exception of nausea, which occurs more frequently with sertraline. In addition, sertraline appears to be more effective than fluoxetine or nortriptyline in the older-than-70 subgroup.[41]Accordingly, a meta-analysis of antidepressants in older adults found that sertraline,paroxetineandduloxetinewere better than placebo.[42]On the other hand, in a 2003 trial theeffect sizewas modest, and there was no improvement inquality of lifeas compared toplacebo.[43]With depression in dementia, there is no benefit of sertraline treatment compared to either placebo ormirtazapine.[44]

Obsessive–compulsive disorder

[edit]

Sertraline is effective for the treatment of OCD in adults,[20]adolescents and children.[45][46][47]It was better tolerated and, based onintention-to-treat analysis,performed better than the gold standard of OCD treatmentclomipramine.[48]Continuing sertraline treatment helps prevent relapses of OCD with long-term data supporting its use for up to 24 months.[49]The sertraline dosages necessary for the effective treatment of OCD are higher than the usual dosage for depression.[50]The onset of action is also slower for OCD than for depression. The treatment recommendation is to start treatment with a half of maximal recommended dose for at least two months. After that, the dose can be raised to the maximal recommended in the cases of unsatisfactory response.[51]

Cognitive behavioral therapyalone is not more effective than sertraline in adolescents and children; however, a combination of these treatments is effective.[47]

Panic disorder

[edit]

Sertraline is superior to placebo for the treatment ofpanic disorder.[20]The response rate was independent of the dose. In addition to decreasing the frequency of panic attacks by about 80% (vs. 45% for placebo) and decreasing general anxiety, sertraline resulted in improvement of quality of life on most parameters. The patients rated as "improved" on sertraline reported better quality of life than the ones who "improved" on placebo. The authors of the study argued that the improvement achieved with sertraline is different and of a better quality than the improvement achieved with placebo.[52][53]Sertraline is equally effective for men and women,[53]and for patients with or without agoraphobia.[54]Previous unsuccessful treatment withbenzodiazepinesdoes not diminish its efficacy.[55]However, the response rate was lower for the patients with more severe panic.[54]Starting treatment simultaneously with sertraline andclonazepam,with subsequent gradual discontinuation of clonazepam, may accelerate the response.[56]

Double-blind comparative studies found sertraline to have the same effect on panic disorder asparoxetineorimipramine.[57]While imprecise, comparison of the results of trials of sertraline with separate trials of other anti-panic agents (clomipramine,imipramine,clonazepam,alprazolam,andfluvoxamine) indicates approximate equivalence of these medications.[52]

Other anxiety disorders

[edit]

Sertraline has been successfully used for the treatment ofsocial anxiety disorder.[58][59]All three major domains of the disorder (fear, avoidance, and physiological symptoms) respond to sertraline.[28]Maintenance treatment, after the response is achieved, prevents the return of the symptoms.[60]The improvement is greater among the patients with later, adult onset of the disorder.[61]In a comparison trial, sertraline was superior toexposure therapy,but patients treated with the psychological intervention continued to improve during a year-long follow-up, while those treated with sertraline deteriorated after treatment termination.[62]The combination of sertraline andcognitive behavioral therapyappears to be more effective in children and young people than either treatment alone.[63]

Sertraline has not been approved for the treatment ofgeneralized anxiety disorder;however, several guidelines recommend it as a first-line medication referring to good quality controlled clinical trials.[64][40][49]

Premenstrual dysphoric disorder

[edit]

Sertraline is effective in alleviating the symptoms ofpremenstrual dysphoric disorder(PMDD), a severe form ofpremenstrual syndrome.[65]Significant improvement was observed in 50–60% of cases treated with sertraline vs. 20–30% of cases on placebo. The improvement began during the first week of treatment, and in addition to mood, irritability, and anxiety, improvement was reflected in better family functioning, social activity and general quality of life. Work functioning and physical symptoms, such as swelling, bloating and breast tenderness, were less responsive to sertraline.[66][67]Taking sertraline only during theluteal phase,that is, the 12–14 days before menses, was shown to work as well as continuous treatment.[65]Continuous treatment with sub-therapeutic doses of sertraline (25 mg vs. usual 50–100 mg) is also effective.[68]

Other indications

[edit]

Sertraline is approved for the treatment ofpost-traumatic stress disorder(PTSD).[20]TheNational Institute for Clinical Excellencerecommends it for patients who prefer drug treatment to a psychological one.[69]Other guidelines also suggest sertraline as a first-line option forpharmacological therapy.[70][40]When necessary, long-term pharmacotherapy can be beneficial.[70]There are both negative and positive clinical trial results for sertraline, which may be explained by the types ofpsychological traumas,symptoms, andcomorbiditiesincluded in the various studies.[49]Positive results were obtained in trials that included predominantly women (75%) with a majority (60%) having physical or sexual assault as the traumatic event.[70]Somewhat contrary to the above suggestions, a meta-analysis of sertraline clinical trials for PTSD found it to be statistically superior to placebo in reduction of PTSD symptoms but the effect size was small.[11]Another meta-analysis relegated sertraline to the second line, proposingtrauma focused psychotherapyas a first-line intervention. The authors noted thatPfizerhad declined to submit the results of a negative trial for the inclusion into the meta-analysis making the results unreliable.[12]

Sertraline when taken daily can be useful for the treatment ofpremature ejaculation.[71]A disadvantage of sertraline is that it requires continuous daily treatment to delay ejaculation significantly.[72]

A 2019systematic reviewsuggested that sertraline may be a good way to controlanger,irritabilityandhostilityin depressed patients and patients with other comorbidities.[73]

Contraindications

[edit]

Sertraline is contraindicated in individuals takingmonoamine oxidase inhibitorsor the antipsychoticpimozide.Sertraline concentrate containsethanoland is therefore contraindicated withdisulfiram.The prescribing information recommends that treatment of the elderly and patients with liver impairment "must be approached with caution". Due to the slower elimination of sertraline in these groups, their exposure to sertraline may be as high as three times the average exposure for the same dose.[20]

Side effects

[edit]

Nausea, ejaculation failure, insomnia, diarrhea, dry mouth, somnolence, dizziness, tremor, headache, excessive sweating, fatigue,restless legs syndromeand decreasedlibidoare the common adverse effects associated with sertraline with the greatest difference fromplacebo.Those that most often resulted in interruption of the treatment are nausea, diarrhea and insomnia.[20]The incidence of diarrhea is higher with sertraline – especially when prescribed at higher doses – in comparison with otherSSRIs.[74]

Over more than six months of sertraline therapy for depression, people showed no significant weight increase.[75]A 30-month-long treatment with sertraline for OCD also resulted in no significant weight gain.[76]Although the difference did not reachstatistical significance,the average weight gain was lower forfluoxetine(1%) but higher forcitalopram,fluvoxamineandparoxetine(2.5%). Of the sertraline group, 4.5% gained a large amount of weight (defined as more than 7% gain). This result compares favorably with placebo, where, according to the literature, 3–6% of patients gained more than 7% of their initial weight. The large weight gain was observed only among female members of the sertraline group; the significance of this finding is unclear because of the small size of the group.[76]

Over a two-week treatment of healthy volunteers, sertraline slightly improved verbalfluencybut did not affect word learning,short-term memory,vigilance,flicker fusion time,choicereaction time,memory span,orpsychomotor coordination.[77][78]In spite of lower subjective rating, that is, feeling that they performed worse, no clinically relevant differences were observed in the objective cognitive performance in a group of people treated for depression with sertraline for 1.5 years as compared to healthy controls.[79]In children and adolescents taking sertraline for six weeks for anxiety disorders, 18 out of 20 measures of memory, attention and alertness stayed unchanged.Divided attentionwas improved and verbal memory underinterference conditionsdecreased marginally. Because of the large number of measures taken, it is possible that these changes were still due to chance.[80]The unique effect of sertraline ondopaminergicneurotransmissionmay be related to these effects on cognition and vigilance.[81][82]

Sertraline has a low level of exposure of an infant through the breast milk and is recommended as the preferred option for the antidepressant therapy of breast-feeding mothers.[83][84]There is 29–42% increase incongenital heart defectsamong children whose mothers were prescribed sertraline during pregnancy,[14][15]with sertraline use in the first trimester associated with 2.7-fold increase inseptal heart defects.[14]

Abrupt interruption of sertraline treatment may result inwithdrawal or discontinuation syndrome.Dizziness, insomnia, anxiety, agitation, and irritability are its common symptoms.[85]It typically occurs within a few days from drug discontinuation and lasts a few weeks.[86]The withdrawal symptoms for sertraline are less severe and frequent than for paroxetine, and more frequent than forfluoxetine.[85][86]In most cases symptoms are mild, short-lived, and resolve without treatment. More severe cases are often successfully treated by temporary reintroduction of the drug with a slower tapering off rate.[87]

Sertraline and SSRI antidepressants in general may be associated withbruxismand othermovement disorders.[88][89]Sertraline appears to be associated withmicroscopic colitis,a rare condition of unknownetiology.[90]

Sexual

[edit]

Like other SSRIs, sertraline is associated with sexual side effects, includingsexual arousal disorder,erectile dysfunctionand difficulty achievingorgasm.Whilenefazodoneandbupropiondo not have negative effects on sexual functioning, 67% of men on sertraline experienced ejaculation difficulties versus 18% before the treatment.[91]Sexual arousaldisorder, defined as "inadequate lubrication and swelling for women and erectile difficulties for men", occurred in 12% of people on sertraline as compared with 1% of patients on placebo. The mood improvement resulting from the treatment with sertraline sometimes counteracted these side effects, so thatsexual desireand overall satisfaction with sex stayed the same as before the sertraline treatment. However, under the action of placebo the desire and satisfaction slightly improved.[92]Some people continue experiencing sexual side effects after they stop taking SSRIs.[93]

Suicide

[edit]

The USFood and Drug Administration(FDA) requires all antidepressants, including sertraline, to carry aboxed warningstating that antidepressants increase the risk of suicide in persons younger than 25 years.[94][95][96]This warning is based on statistical analyses conducted by two independent groups of FDA experts that found a 100% increase of suicidal thoughts and behavior in children and adolescents, and a 50% increase in the 18–24 age group.[97][98][99]

Suicidal ideationand behavior in clinical trials are rare. For the above analysis, the FDA combined the results of 295 trials of 11 antidepressants for psychiatric indications in order to obtainstatistically significantresults. Considered separately, sertraline use in adults decreased the odds of suicidal behavior with a marginal statistical significance by 37%[99]or 50%[98]depending on the statistical technique used. The authors of the FDA analysis note that "given the large number of comparisons made in this review, chance is a very plausible explanation for this difference".[98]The more complete data submitted later by the sertraline manufacturer Pfizer indicated increased suicidal behavior.[100]Similarly, the analysis conducted by the UKMHRAfound a 50% increase of odds of suicide-related events, not reaching statistical significance, in the patients on sertraline as compared to the ones on placebo.[101][102]

Overdose

[edit]

Acute overdosage is often manifested byemesis,lethargy,ataxia,tachycardiaandseizures.Plasma, serum or blood concentrations of sertraline and norsertraline, its majoractive metabolite,may be measured to confirm a diagnosis of poisoning in hospitalized patients or to aid in the medicolegal investigation of fatalities.[103]As with most other SSRIs its toxicity in overdose is considered relatively low.[104][105]

Interactions

[edit]

As with other SSRIs, sertraline may increase the risk of bleeding withNSAIDs(ibuprofen,naproxen,mefenamic acid),antiplatelet drugs,anticoagulants,Omega -3 fatty acids,vitamin E,and garlicsupplementsdue to sertraline's inhibitory effects onplatelet aggregationvia blockingserotonin transporterson platelets.[106]Sertraline, in particular, may potentially diminish the efficacy oflevothyroxine.[107]

Sertraline is a moderateinhibitorofCYP2D6andCYP2B6in vitro.[7]Accordingly, in human trials it caused increased blood levels of CYP2D6substratessuch asmetoprolol,dextromethorphan,desipramine,imipramineandnortriptyline,as well as theCYP3A4/CYP2D6 substratehaloperidol.[108][109][110]This effect is dose-dependent; for example, co-administration with 50 mg of sertraline resulted in 20% greater exposure to desipramine, while 150 mg of sertraline led to a 70% increase.[8][111]In a placebo-controlled study, the concomitant administration of sertraline andmethadonecaused a 40% increase in blood levels of the latter, which is primarily metabolized by CYP2B6.[112]

Sertraline had a slight inhibitory effect on the metabolism ofdiazepam,tolbutamideandwarfarin,which areCYP2C9orCYP2C19substrates; the clinical relevance of this effect was unclear.[8]As expected fromin vitrodata, sertraline did not alter the human metabolism of the CYP3A4 substrateserythromycin,alprazolam,carbamazepine,clonazepam,andterfenadine;neither did it affect metabolism of theCYP1A2substrateclozapine.[8][20][113][7]

Sertraline had no effect on the actions ofdigoxinandatenolol,which are not metabolized in the liver.[5]Case reportssuggest that taking sertraline withphenytoinorzolpidemmay induce sertraline metabolism and decrease its efficacy,[114][115]and that taking sertraline withlamotriginemay increase the blood level of lamotrigine, possibly by inhibition of glucuronidation.[116]

CYP2C19 inhibitoresomeprazoleincreased sertraline concentrations in blood plasma by approximately 40%.[117]

Clinical reports indicate that interaction between sertraline and theMAOIsisocarboxazidandtranylcyprominemay causeserotonin syndrome.In a placebo-controlled study in which sertraline was co-administered withlithium,35% of the subjects experienced tremors, while none of those taking placebo did.[8]

Pharmacology

[edit]

Pharmacodynamics

[edit]
Molecular targets of sertraline[118]
Site Ki(nM) Species References
SERTTooltip Serotonin transporter 0.15–3.3 Human [119][120][121]
NETTooltip Norepinephrine transporter 420–925 Human [119][120][121]
DATTooltip Dopamine transporter 22–315 Human [119][120][121]
5-HT1A >35,000 Human [122]
5-HT2A 2,207 Rat [121]
5-HT2C 2,298 Pig [121]
α1A 1900 Human [123]
α1B 3,500 Human [123]
α1D 2,500 Human [123]
α2 477–4,100 Human [120][122]
D2 10,700 Human [122]
H1 24,000 Human [122]
mAChTooltip Muscarinic acetylcholine receptors 427–2,100 Human [121][122][124]
σ1 32–57 Rat [125][126]
σ2 5,297 Rat [126]
Values areKi(nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to or inhibits the site.

Sertraline is aselective serotonin reuptake inhibitor(SSRI). By binding to theserotonin transporter(SERT) it inhibits neuronalreuptakeofserotoninand potentiatesserotonergicactivity in thecentral nervous system.[20]Over time, this leads to a downregulation of pre-synaptic5-HT1Areceptors, which is associated with an improvement in passive stress tolerance, and delayed downstream increase in expression ofbrain-derived neurotrophic factor(BDNF), which may contribute to a reduction in negative affective biases.[127][128]It does not significantly effecthistamine,acetylcholine,GABAorbenzodiazepinereceptors.[20]

Sertraline also shows relatively high activity as an inhibitor of thedopamine transporter(DAT)[119][129][130]and antagonist of thesigmaσ1receptor(but not theσ2receptor).[125][126][131]However, sertraline affinity for its main target (SERT) is much greater than its affinity for σ1receptor and DAT.[118][119][126][125]Although there could be a role for the σ1receptor in thepharmacologyof sertraline, the significance of this receptor in its actions is unclear.[31]Similarly, the clinical relevance of sertraline's blockade of the dopamine transporter is uncertain.[119]

Pharmacokinetics

[edit]
Desmethylsertraline,the majormetaboliteof sertaline

Absorption

[edit]

Following a single oral dose of sertraline, mean peak blood levels of sertraline occur between 4.5 and 8.4 hours.[5]Bioavailabilityis likely linear and dose-proportional over a dose range of 150 to 200 mg.[5]Concomitant intake of sertraline with food slightly increases sertraline peak levels and total exposure.[5]There is an approximate 2-fold accumulation of sertraline with continuous administration andsteady-state levelsare reached within one week.[5]

Distribution

[edit]

Sertraline is highlyplasma protein bound(98.5%) across a concentration range of 20 to 500 ng/mL.[5]Despite the high plasma protein binding, sertraline and itsmetabolitedesmethylsertralineat respective tested concentrations of 300 ng/mL and 200 ng/mL were found not to interfere with the plasma protein binding ofwarfarinandpropranolol,two other highly plasma protein-bound drugs.[5]

Metabolism

[edit]

Sertraline is subject to extensivefirst-pass metabolism,as indicated by a small study ofradiolabeledsertraline in which less than 5% of plasmaradioactivitywas unchanged sertraline in two males.[5]The principalmetabolic pathwayfor sertraline isN-demethylationintodesmethylsertraline(N-desmethylsertraline) mainly byCYP2B6.[5][9]Reduction,hydroxylation,andglucuronideconjugationof both sertraline and desmethylsertraline also occur.[5]Desmethylsertraline, whilepharmacologically active,is substantially (50-fold) weaker than sertraline as aserotonin reuptake inhibitorand its influence on the clinical effects of sertraline is thought to be negligible.[5][120][132]Based onin vitrostudies, sertraline ismetabolizedby multiplecytochrome 450isoforms;[9][133]however, it appears that in the human bodyCYP2C19plays the most important role, followed byCYP2B6.[134]In addition to the cytochrome P450 system, sertraline can beoxidativelydeaminatedin vitrobymonoamine oxidases;[5]however, thismetabolic pathwayhas never been studiedin vivo.[9]

Elimination

[edit]

Theelimination half-lifeof sertraline is on average 26 hours, with a range of 13 to 45 hours.[5][8]The half-life of sertraline is longer in women (32 hours) than in men (22 hours), which leads to 1.5-fold higher exposure to sertraline in women compared to men.[8]The elimination half-life of desmethylsertraline is 62 to 104 hours.[5]

In a small study of two males, sertraline wasexcretedto similar degrees inurineandfeces(40 to 45% each within 9 days).[5]Unchanged sertraline was not detectable in urine, whereas 12 to 14% unchanged sertraline was present in feces.[5]

Pharmacogenomics

[edit]

CYP2C19andCYP2B6are thought to be the keycytochrome P450enzymesinvolved in themetabolismof sertraline.[134]Relative to CYP2C19normal (extensive) metabolizers,poor metabolizershave 2.7-fold higher levels of sertraline[135]andintermediate metabolizershave 1.4-fold higher levels.[136]In contrast, CYP2B6 poor metabolizers have 1.6-fold higher levels of sertraline and intermediate metabolizers have 1.2-fold higher levels.[134]

History

[edit]
Skeletal formulaeof thiothixene, lometraline and tametraline, from which sertraline was derived. Commonalities to the structure of sertraline are highlighted in red.

The history of sertraline dates back to the early 1970s, whenPfizerchemist Reinhard Sarges invented a novel series of psychoactive compounds, includinglometraline,based on the structures of the neurolepticsthiothixeneandpinoxepin.[137][138]Further work on these compounds led totametraline,anorepinephrineand weakerdopamine reuptake inhibitor.Development of tametraline was soon stopped because of undesiredstimulanteffects observed in animals. A few years later, in 1977, pharmacologistKenneth Koe,after comparing the structural features of a variety of reuptake inhibitors, became interested in the tametraline series. He asked another Pfizer chemist, Willard Welch, to synthesize some previously unexplored tametraline derivatives. Welch generated a number of potent norepinephrine andtriple reuptakeinhibitors, but to the surprise of the scientists, one representative of the generally inactivecis-analogswas a serotonin reuptake inhibitor. Welch then preparedstereoisomersof this compound, which were testedin vivoby animalbehavioral scientistAlbert Weissman. The most potent and selective (+)-isomer was taken into further development and eventually named sertraline. Weissman and Koe recalled that the group did not set up to produce an antidepressant of the SSRI type—in that sense their inquiry was not "very goal driven", and the discovery of the sertraline molecule wasserendipitous.According to Welch, they worked outside the mainstream at Pfizer, and even "did not have a formal project team". The group had to overcome initial bureaucratic reluctance to pursue sertraline development, as Pfizer was considering licensing an antidepressant candidate from another company.[137][139][140]

Sertraline was approved by the USFood and Drug Administration(FDA) in 1991 based on the recommendation of the Psychopharmacological Drugs Advisory Committee; it had already become available in theUnited Kingdomthe previous year.[141]The FDA committee achieved a consensus that sertraline was safe and effective for the treatment ofmajor depression.During the discussion, Paul Leber, the director of the FDA Division of Neuropharmacological Drug Products, noted that granting approval was a "tough decision", since the treatment effect onoutpatientswith depression had been "modest to minimal". Other experts emphasized that the drug's effect on inpatients had not differed fromplaceboand criticized poor design of the clinical trials by Pfizer.[142]For example, 40% of participants dropped out of the trials, significantly decreasing theirvalidity.[143]

Until 2002, sertraline was only approved for use in adults ages 18 and over; that year, it was approved by the FDA for use in treating children aged 6 or older with severe OCD. In 2003, the UKMedicines and Healthcare products Regulatory Agencyissued a guidance that, apart fromfluoxetine(Prozac), SSRIs are not suitable for the treatment of depression in patients under 18.[144][145]However, sertraline can still be used in the UK for the treatment of OCD in children and adolescents.[146]In 2005, the FDA added aboxed warningconcerning pediatric suicidal behavior to allantidepressants,including sertraline. In 2007, labeling was again changed to add a warning regarding suicidal behavior in young adults ages 18 to 24.[147]

Society and culture

[edit]

Generic availability

[edit]

The US patent for Zoloft expired in 2006,[148]and sertraline is available ingenericform and is marketed under many brand names worldwide.[1]

Brand names

[edit]

In the US, Zoloft is marketed byViatrisafter Upjohn was spun off from Pfizer.[149][150][151]

Interest during COVID-19 pandemic

[edit]

Sertraline has been the most sought-after antidepressant worldwide before, during, and after theCOVID-19 pandemic,according toGoogle Trendsdata. The pandemic has led to an increase in searches for antidepressants, with sertraline,fluoxetine,duloxetine,andvenlafaxineshowing the highest search volumes, whereas searches ofcitalopramdecreased during the pandemic.[152]

Other uses

[edit]

Sertraline may be useful to treatmurine Zaire ebolavirus(murine EBOV).[153]TheWorld Health Organization(WHO) considers this a promising area of research.[153]

Lass-Flörlet al.,2003 finds it significantly inhibitsphospholipase Bin the fungal genusCandida,reducingvirulence.[154]

Sertraline is also a very effective leishmanicide.[155]Specifically, Palit & Ali 2008 find that sertraline kills almost allpromastigotesofLeishmania donovani.[155]

Sertraline is stronglyantibacterialagainst some species.[155]It is also known to act as aphotosensitizerof bacterial surfaces.[156]In combination with antibacterials its photosensitization effect reversesantibacterial resistance.[156]As such sertraline shows promise forfood preservation.[156]

Lass-Flörlet al.,2003 finds this compound acts as afungicideagainstCandida parapsilosis.[157]Its anti-Cpeffect is indeed due to itsserotonergicactivity and not its other effects.[157]

Sertraline is a promisingtrypanocide.[158]It acts at several differentlife stagesand against severalstrains.[158]Sertraline's trypanocidalmechanism of actionis by way of interference withbioenergetics.[158]

See also

[edit]

References

[edit]
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