Sertraline

Sertraline
Clinical data
Pronunciation/ˈsɜːrtrəˌln/ sur-trə-LEEN
Trade namesZoloft, Lustral, Setrona, others
AHFS/Drugs.comMonograph
MedlinePlusa697048
License data
Pregnancy
category
  • AU: C
Addiction
liability
None
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)
  • CA: ℞-only
  • NZ: Prescription only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability44%
Protein binding98.5%
MetabolismLiver (primarily N-demethylation mainly by CYP2B6; also metabolism by CYP2C19, others)
MetabolitesDesmethylsertraline
• Others (e.g., hydroxylated metabolites, glucuronide conjugates)
Elimination half-life• Sertraline: 26 hours (32 hours in females, 22 hours in males; range 13–45 hours)
• Desmethylsertraline: 62–104 hours
ExcretionUrine (40–45%)
Feces (40–45%)
Identifiers
  • (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H17Cl2N
Molar mass306.23 g·mol−1
3D model (JSmol)
  • ClC1=CC=C([C@H]2C3=C([C@H](CC2)NC)C=CC=C3)C=C1Cl
  • InChI=1S/C17H17NCl2/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/s1 Y
  • Key:VGKDLMBJGBXTGI-SJCJKPOMSA-N Y
  (verify)

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.

Sertraline was developed by scientists at Pfizer and approved for medical use in the United States in 1991. It is on the World Health Organization's List of Essential Medicines and available as a generic medication. In 2016, sertraline was the most commonly prescribed psychotropic medication in the United States. It was also the eleventh most commonly prescribed medication in the United States, with more than 39 million prescriptions in 2022, and sertraline ranks among the top 10 most prescribed medications in Australia between 2017 and 2023.

For alleviating the symptoms of depression, the drug is usually second in potency to another SSRI, escitalopram. Sertraline's effectiveness is similar to that of other antidepressants in its class, such as fluoxetine and paroxetine, which are also considered first-line treatments and are better tolerated than the older tricyclic antidepressants.