Sertraline

Sertraline, sold under the brand name Zoloft among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. The efficacy of sertraline for depression is similar to that of other antidepressants, and the differences are mostly confined to side effects. Sertraline is better tolerated than the older tricyclic antidepressants. Sertraline is effective for panic disorder, social anxiety disorder, generalized anxiety disorder (GAD), and obsessive–compulsive disorder (OCD). Although approved for post-traumatic stress disorder (PTSD), sertraline leads to only modest improvement in this condition. Sertraline also alleviates the symptoms of premenstrual dysphoric disorder (PMDD) and can be used in sub-therapeutic doses or intermittently (luteal phase dosing) for its treatment.

Sertraline
Clinical data
Pronunciation/ˈsɜːrtrəˌln/
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/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/s1 Y
  • Key:VGKDLMBJGBXTGI-SJCJKPOMSA-N Y
  (verify)

Sertraline shares the common side effects and contraindications of other SSRIs, with high rates of diarrhea, nausea, insomnia, 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 MAO inhibitor medication: 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 invented and 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. It is available as a generic medication. In 2016, sertraline was the most commonly prescribed psychotropic medication in the United States and in 2021, it was the eleventh most commonly prescribed medication in the United States, with over 39 million prescriptions.

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