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Sertraline information


Sertraline
Clinical data
Pronunciation/ˈsɜːrtrəˌln/
Trade namesZoloft, Lustral, Setrona, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa697048
License data
  • US DailyMed: Sertraline
Pregnancy
category
  • AU: C[2]
Addiction
liability
None[3]
Routes of
administration
By mouth
Drug classSelective serotonin reuptake inhibitor (SSRI)
ATC code
  • N06AB06 (WHO)
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)
Pharmacokinetic data
Bioavailability44%[citation needed]
Protein binding98.5%[citation needed]
MetabolismLiver (primarily N-demethylation mainly by CYP2B6; also metabolism by CYP2C19, others)[5][9]
Metabolites• Desmethylsertraline
• Others (e.g., hydroxylated metabolites, glucuronide conjugates)[5]
Elimination half-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
IUPAC name
  • (1S,4S)-4-(3,4-Dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
  • 79617-96-2 checkY
PubChem CID
  • 68617
IUPHAR/BPS
  • 4798
DrugBank
  • DB01104 checkY
ChemSpider
  • 61881 checkY
UNII
  • QUC7NX6WMB
KEGG
  • D02360 checkY
  • as HCl: D00825 checkY
ChEBI
  • CHEBI:9123 checkY
ChEMBL
  • ChEMBL809 checkY
CompTox Dashboard (EPA)
  • DTXSID6023577 Edit this at Wikidata
Chemical and physical data
FormulaC17H17Cl2N
Molar mass306.23 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • ClC1=CC=C([C@H]2C3=C([C@H](CC2)NC)C=CC=C3)C=C1Cl
InChI
  • 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 checkY
  • Key:VGKDLMBJGBXTGI-SJCJKPOMSA-N checkY
  (verify)

Sertraline, sold under the brand name Zoloft among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class.[10] The effectiveness 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.[11][12] 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.[13]

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 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.[14][15]

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.[16] It is available as a generic 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 39 million prescriptions.[18][19]

  1. ^ Cite error: The named reference Brand2015 was invoked but never defined (see the help page).
  2. ^ "Sertraline (Zoloft) Use During Pregnancy". Drugs.com. 4 May 2020. Retrieved 17 May 2020.
  3. ^ Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled. CRC Press. p. 26. ISBN 9780824744977.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  5. ^ a b c d e f Cite error: The named reference FDALabel was invoked but never defined (see the help page).
  6. ^ Brunton L, Chabner B, Knollman B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (Twelfth ed.). McGraw Hill Professional. ISBN 978-0-07-176939-6.
  7. ^ Cite error: The named reference pmid16192315 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference pmid12452737 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference pmid15547048 was invoked but never defined (see the help page).
  10. ^ a b "Sertraline Hydrochloride". Drugs.com. The American Society of Health-System Pharmacists. Retrieved 8 January 2018.
  11. ^ Cite error: The named reference pmid25644881 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference pmid27126398 was invoked but never defined (see the help page).
  13. ^ Yonkers KA, Kornstein SG, Gueorguieva R, Merry B, Van Steenburgh K, Altemus M (October 2015). "Symptom-Onset Dosing of Sertraline for the Treatment of Premenstrual Dysphoric Disorder: A Randomized Clinical Trial". JAMA Psychiatry. 72 (10): 1037–1044. doi:10.1001/jamapsychiatry.2015.1472. PMC 4811029. PMID 26351969.
  14. ^ Cite error: The named reference pmid30415641 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid33354752 was invoked but never defined (see the help page).
  16. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  17. ^ Grohol JM (12 October 2017). "Top 25 Psychiatric Medications for 2016". Psych Central. Retrieved 22 October 2018.
  18. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  19. ^ "Sertraline - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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are avoided in patients who have had a recent history with hypomania. Sertraline has often been debated to have side effects that can trigger hypomania...

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Antidepressant

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the most effective and well-tolerated are escitalopram, paroxetine, sertraline, agomelatine, and mirtazapine. For children and adolescents with moderate...

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drugs. A causative role has not been established. Pfizer has denied that sertraline can cause such effects. Serotonin reuptake inhibitors (SSRI) have been...

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selective serotonin reuptake inhibitors (SSRIs) fluvoxamine, paroxetine, sertraline, and escitalopram; others such as citalopram and fluoxetine are either...

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Paroxetine

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1–4 mg/L in acute lethal overdose situations. Along with the other SSRIs, sertraline and fluoxetine, paroxetine is considered a low-risk drug in cases of overdose...

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MDMA

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Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam...

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Fluvoxamine

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cardiovascular complications), despite its age. Compared to escitalopram and sertraline, indeed, fluvoxamine's gastrointestinal profile may be less intense, often...

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Ketamine

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XP21279 Atypical antipsychotics: Alentemol (U-66444B) Aripiprazole (+sertraline) Aripiprazole lauroxil Bifeprunox Brexpiprazole Brilaroxazine Cariprazine...

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LSD

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