Trazodone

Trazodone
Clinical data
Trade namesDesyrel, Trittico, others[1]
Other namesAF-1161
AHFS/Drugs.comMonograph
MedlinePlusa681038
License data
Dependence
liability		Low[2]
Addiction
liability		Low–moderate[2]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only[4][5]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityBy mouth: 65%[6]
Protein binding89–95%[7]
MetabolismLiver (CYP3A4, CYP2D6, CYP1A2?)[10][16][11][17][18]
MetabolitesmCPPTooltip meta-Chlorophenylpiperazine[8]
Onset of actionBy mouth: 1 hour (Tmax)[9]
Elimination half-life• Trazodone (IR): 4–15 hours[10][11][12][13]
• Trazodone (ER): 9–13 hours[14][11][12]
• mCPPTooltip meta-Chlorophenylpiperazine: 3–16 hours[10][11][13][15]
ExcretionUrine: 70–75%[6]
Feces: 21%[6]
Identifiers
IUPAC name
  • 2-{3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.039.364
Chemical and physical data
FormulaC19H22ClN5O
Molar mass371.87 g·mol−1
3D model (JSmol)
Melting point87 °C (189 °F)
SMILES
  • Clc4cccc(N3CCN(CCCN1/N=C2/C=C\C=C/N2C1=O)CC3)c4
InChI
  • InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2 Y
  • Key:PHLBKPHSAVXXEF-UHFFFAOYSA-N Y
  (verify)

Trazodone is an antidepressant medication[19] used to treat major depressive disorder, anxiety disorders, and insomnia.[19] It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class.[20][21] The medication is taken orally.[19]

Common side effects include dry mouth, feeling faint, vomiting, and headache.[19] More serious side effects may include suicide, mania, irregular heart rate, and pathologically prolonged erections.[19] It is unclear if use during pregnancy or breastfeeding is safe.[22] Trazodone also has sedating effects.[23]

Trazodone was approved for medical use in the United States in 1981.[19] It is available as a generic medication.[19] In 2022, it was the eighteenth most commonly prescribed medication in the United States, with more than 27 million prescriptions.[24][25]

  1. ^ "Trazodone". Drugs.com. Retrieved 9 February 2019.
  2. ^ a b Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled. CRC Press. p. 26. ISBN 978-0-8247-4497-7.
  3. ^ 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.
  4. ^ Cite error: The named reference Desyrel FDA label was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Trazodone FDA label was invoked but never defined (see the help page).
  6. ^ a b c Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Oct 1]. Greenwood Village, CO: Thomsen Healthcare; 2013.
  7. ^ "Trazodone". DrugBank. Retrieved 7 June 2015.
  8. ^ Preskorn SH, Stanga CY, Feighner JP, Ross J (2012). Antidepressants: Past, Present and Future. Springer Science & Business Media. pp. 68–. ISBN 978-3-642-18500-7.
  9. ^ "MicroMedex DrugPoints – Trazodone". Pharmacy Choice. Retrieved 20 April 2017.
  10. ^ a b c Cite error: The named reference pmid10379419 was invoked but never defined (see the help page).
  11. ^ a b c d Cite error: The named reference pmid22115401 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference pmid23192413 was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference pmid20173086 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid26678742 was invoked but never defined (see the help page).
  15. ^ Schatzberg AF, Nemeroff CB (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology (5th ed.). American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.
  16. ^ Cite error: The named reference pmid31379379 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference pmid9836023 was invoked but never defined (see the help page).
  18. ^ Lemke TL, Williams DA (2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 615. ISBN 978-1-60913-345-0.
  19. ^ a b c d e f g "Trazodone". The American Society of Health-System Pharmacists. 17 March 2021. Retrieved 24 December 2021.
  20. ^ Stahl SM (2008). Stahl's Essential Psychopharmacology: Neuroscientific Basis and Practical Applications. Cambridge University Press. p. 567. ISBN 978-0-521-85702-4.
  21. ^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 586. ISBN 978-0-7817-6879-5.
  22. ^ "Trazodone Use During Pregnancy". Drugs.com. Retrieved 7 January 2018.
  23. ^ British national formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 257–58. ISBN 978-0-85711-156-2.
  24. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  25. ^ "Trazodone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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