File:Sertraline.svg · Wikimedia Commons · See Wikimedia Commons
sertraline
Sign in to saveAlso known as CP-51974-1, CP-519741, (1S-cis)-1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine, CP 51974, (+)-sertraline, (1S,4S)-sertraline, cis-(+)-sertraline
Sertraline, sold under the brand name Zoloft among others, is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class used to treat major depressive disorder, generalized anxiety disorder, social anxiety disorder, obsessive–compulsive disorder (OCD), panic disorder, and premenstrual dysphoric disorder. Although also having approval for post-traumatic stress disorder (PTSD), findings indicate it leads to only modest improvements in symptoms associated with this condition.
OverviewAI-generated
Sertraline is a chemical compound with the formula C₁₇H₁₇Cl₂N. Its IUPAC name is (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine. The substance has a mass of 305.074 and a weight of 306.2. It possesses a defined daily dose of 50.
Chemical properties include an xlogp of 4.8 and a topological polar surface area of 12. The molecule contains one hydrogen bond donor and one hydrogen bond acceptor, with a charge of 0. Sertraline is referenced by 1,005 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464389436
- Drug.image
- Sertraline.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Sertraline_3D_Ball-And-Stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Zoloft, Lustral, Setrona, others
- Drug.MedlinePlus
- a697048
- Drug.DailyMedID
- Sertraline
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth
- Drug.class
- Selective serotonin reuptake inhibitor (SSRI)
- Drug.addiction_liability
- None
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AB06
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C17H17Cl2N
- Molecular weight
- 306.2 g/mol
- IUPAC name
- (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
- SMILES
- CN[C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
- InChIKey
- VGKDLMBJGBXTGI-SJCJKPOMSA-N
- XLogP
- 4.8
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
6,949 papers- Clinical pharmacokinetics of sertraline.Clinical pharmacokinetics · 2002
- Brexpiprazole and Sertraline Combination Treatment in Posttraumatic Stress Disorder: A Phase 3 Randomized Clinical Trial.JAMA psychiatry · 2025
- Selection of the optimal dose of sertraline for depression: A dose-response meta-analysis of randomized controlled trials.Psychiatry research · 2023
- Sertraline-Induced Acute Pancreatitis: A Case Report and Literature Review.Alternative therapies in health and medicine · 2024
- Sertraline and breastfeeding: review and meta-analysis.Archives of women's mental health · 2015
via PubMed
Wikidata facts
- Mass
- 305.074
- Has use
- medication
Show 10 more facts
- significant drug interaction
- (−)-selegiline
- Commons category
- Sertraline
- chemical formula
- C₁₇H₁₇Cl₂N
- medical condition treated
- social anxiety disorder
- isomeric SMILES
- CN[C@H]1CC[C@H](C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
- canonical SMILES
- CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl
- World Health Organisation international non-proprietary name
- sertraline
- defined daily dose
- 50
- subject has role
- antidepressant
- physically interacts with
- solute carrier family 6 member 4
via Wikidata · CC0
~33 min read
Encyclopedic overview
34 sectionsContents
- Medical uses
- Depression
- Comparison with other antidepressants
- Depression in elderly
- Obsessive–compulsive disorder
- Panic disorder
- Other anxiety disorders
- Premenstrual dysphoric disorder
- Other indications
- Contraindications
- Side effects
- Sexual
- Suicide
- Therapeutic dosage
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Pharmacogenomics
- Chemistry
- History
- Society and culture
- Generic availability
- Brand names
- Interest during COVID-19 pandemic
- Research
- See also
- References
- External links
Sertraline, sold under the brand name Zoloft among others, is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class used to treat major depressive disorder, generalized anxiety disorder, social anxiety disorder, obsessive–compulsive disorder (OCD), panic disorder, and premenstrual dysphoric disorder. Although also having approval for post-traumatic stress disorder (PTSD), findings indicate it leads to only modest improvements in symptoms associated with this condition.
The drug shares the common side effects and contraindications of other SSRIs, with high rates of nausea, diarrhea, headache, insomnia, mild sedation, dry mouth, and sexual dysfunction, but it appears not to lead to much weight gain, and its effects on cognitive performance are mild. Similar to other antidepressants, the use of sertraline for depression may be associated with a mildly elevated rate of suicidal thoughts in people under the age of 25 years old. It should not be used together with monoamine oxidase inhibitors (MAOIs): this combination may cause serotonin syndrome, which can be life-threatening in some cases. Sertraline taken during pregnancy is associated with an increase in congenital heart defects in newborns.
Excerpted from Wikipedia’s “sertraline” article, available under the CC BY-SA 4.0 licence.