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Trazodone information


Trazodone
Clinical data
Trade namesDesyrel, Trittico, others[1]
Other namesAF-1161
AHFS/Drugs.comMonograph
MedlinePlusa681038
License data
  • US DailyMed: Trazodone
Dependence
liability
None[2]
Addiction
liability
None[2]
Routes of
administration
By mouth
ATC code
  • N06AX05 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[4]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[3]Rx-only[5][6]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityBy mouth: 65%[7][failed verification]
Protein binding89–95%[8]
MetabolismLiver (CYP3A4, CYP2D6, CYP1A2?)[11][17][12][18][19]
MetabolitesmCPPTooltip meta-Chlorophenylpiperazine[9]
Onset of actionBy mouth: 1 hour (Tmax)[10]
Elimination half-life• Trazodone (IR): 4–15 hours[11][12][13][14]
• Trazodone (ER): 9–13 hours[15][12][13]
mCPPTooltip meta-Chlorophenylpiperazine: 3–16 hours[11][12][14][16]
ExcretionUrine: 70–75%[7]
Feces: 21%[7]
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
  • 19794-93-5 checkY
PubChem CID
  • 5533
IUPHAR/BPS
  • 213
DrugBank
  • DB00656 checkY
ChemSpider
  • 5332 checkY
UNII
  • YBK48BXK30
KEGG
  • D08626 checkY
  • as HCl: D00820 checkY
ChEBI
  • CHEBI:9654 checkY
ChEMBL
  • ChEMBL621 checkY
CompTox Dashboard (EPA)
  • DTXSID5045043 Edit this at Wikidata
ECHA InfoCard100.039.364 Edit this at Wikidata
Chemical and physical data
FormulaC19H22ClN5O
Molar mass371.87 g·mol−1
3D model (JSmol)
  • Interactive image
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 checkY
  • Key:PHLBKPHSAVXXEF-UHFFFAOYSA-N checkY
  (verify)

Trazodone, sold under many brand names,[1] is an antidepressant medication.[20] It is used to treat major depressive disorder, anxiety disorders, and insomnia.[20] The medication is taken orally.[20]

Common side effects include dry mouth, feeling faint, vomiting, and headache.[20] More serious side effects may include suicide, mania, irregular heart rate, and pathologically prolonged erections.[20] It is unclear if use during pregnancy or breastfeeding is safe.[21] It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class.[22][23] Trazodone also has sedating effects.[24]

Trazodone was approved for medical use in the United States in 1981.[20] It is available as a generic medication.[20] In 2021, it was the 22nd most commonly prescribed medication in the United States, with more than 26 million prescriptions.[25][26]

  1. ^ a b "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. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  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. ^ Cite error: The named reference Desyrel FDA label was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Trazodone FDA label was invoked but never defined (see the help page).
  7. ^ a b c Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Oct 1]. Greenwood Village, CO: Thomsen Healthcare; 2013.
  8. ^ "Trazodone". DrugBank. Retrieved 7 June 2015.
  9. ^ 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.
  10. ^ "MicroMedex DrugPoints – Trazodone". Pharmacy Choice. Retrieved 20 April 2017.
  11. ^ a b c Cite error: The named reference pmid10379419 was invoked but never defined (see the help page).
  12. ^ a b c d Cite error: The named reference pmid22115401 was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference pmid23192413 was invoked but never defined (see the help page).
  14. ^ a b Cite error: The named reference pmid20173086 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid26678742 was invoked but never defined (see the help page).
  16. ^ 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.
  17. ^ Cite error: The named reference pmid31379379 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference pmid9836023 was invoked but never defined (see the help page).
  19. ^ Lemke TL, Williams DA (2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 615. ISBN 978-1-60913-345-0.
  20. ^ a b c d e f g "Trazodone". The American Society of Health-System Pharmacists. 17 March 2021. Retrieved 24 December 2021.
  21. ^ "Trazodone Use During Pregnancy". Drugs.com. Retrieved 7 January 2018.
  22. ^ Stahl SM (2008). Stahl's Essential Psychopharmacology: Neuroscientific Basis and Practical Applications. Cambridge University Press. p. 567. ISBN 978-0-521-85702-4.
  23. ^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 586. ISBN 978-0-7817-6879-5.
  24. ^ British national formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 257–58. ISBN 978-0-85711-156-2.
  25. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  26. ^ "Trazodone – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Trazodone

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Trazodone, sold under many brand names, is an antidepressant medication. It is used to treat major depressive disorder, anxiety disorders, and insomnia...

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List of adverse effects of trazodone

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This is a list of adverse effects of the antidepressant trazodone, sorted by frequency of occurrence. Very common (>10% incidence) adverse effects include:...

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Palinopsia

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visual snow, HPPD, prescription drugs, head trauma, or may be idiopathic. Trazodone, nefazodone, mirtazapine, topiramate, clomiphene, oral contraceptives...

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Etoperidone

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longer marketed or was never marketed. It is a phenylpiperazine related to trazodone and nefazodone in chemical structure and is a serotonin antagonist and...

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Serotonin antagonist and reuptake inhibitor

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Lorpiprazole (Normarex) Mepiprazole (Psigodal) Nefazodone (Serzone, Nefadar) Trazodone (Desyrel) Vilazodone (Viibryd) – a related drug but does not fit into...

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Akathisia

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caused akathisia in certain individuals. as well as diphenhydramine, trazodone, benzatropine, cyproheptadine, and beta blockers, particularly propranolol...

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Atypical antidepressant

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iprindole, mianserin, mirtazapine, nefazodone, opipramol, tianeptine, and trazodone. The agents vilazodone and vortioxetine are partly atypical. Typical antidepressants...

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Mepiprazole

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symptoms of IBS in some patients. Similarly to other phenylpiperazines like trazodone, nefazodone, and etoperidone, mepiprazole produces mCPP as an active metabolite...

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Lorpiprazole

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serotonin antagonist and reuptake inhibitor (SARI) in the same group as trazodone, nefazodone, and etoperidone. Acaprazine Enpiprazole Mepiprazole Tolpiprazole...

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Nefazodone

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patient years. Nefazodone is a phenylpiperazine compound and is related to trazodone. It has been described as a serotonin antagonist and reuptake inhibitor...

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Triazolopyridine

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structure includes a trazolopyridine-derived ring system. One example is trazodone. Other pharmaceutical drugs that contain a triazolopyridine ring system...

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Hypnotic

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effects. Examples include: Serotonin antagonists and reuptake inhibitors Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine Tetracyclic...

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Alcohol withdrawal syndrome

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found to influence relapse rate. Studies have found that magnesium or trazodone can help treat the persisting withdrawal symptom of insomnia in recovering...

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Zopiclone

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Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Midaflur Opioids (e.g., morphine) Passion flower Scopolamine Trazodone UMB68 Valnoctamide...

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Nimetazepam

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frequently than nimetazepam for this purpose. Antidepressants such as trazodone and mirtazapine or Z-drugs like zopiclone and zolpidem are first line...

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Murder of Shad Thyrion

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interrogation that she and Thyrion also smoked methamphetamine, and injected Trazodone at the apartment after the friend left. The couple then returned to Thyrion's...

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Sedative

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Imipramine (Tofranil) Mirtazapine (Remeron) Nefazodone Nortriptyline (Pamelor) Trazodone (Desyrel) Trimipramine (Surmontil) Antipsychotics Asenapine (Saphris)...

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Secobarbital

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Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Midaflur Opioids (e.g., morphine) Passion flower Scopolamine Trazodone UMB68 Valnoctamide...

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Cocaine

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Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine Serotonin–norepinephrine reuptake inhibitors:...

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Sertraline

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SARIsTooltip Serotonin antagonist and reuptake inhibitors Etoperidone Nefazodone Trazodone SMSTooltip Serotonin modulator and stimulators Vilazodone Vortioxetine...

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Diphenhydramine

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Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Midaflur Opioids (e.g., morphine) Passion flower Scopolamine Trazodone UMB68 Valnoctamide...

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MDMA

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Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics (e.g...

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Clitoris

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of the clitoris. Drugs may cause or affect clitoral priapism. The drug trazodone is known to cause male priapism as a side effect, but there is only one...

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Phenylpiperazine

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[1044-59-3] Nefazodone Niaprazine Oxypertine PD-158771 [189152-50-9] PO-219 Trazodone WIN 18,437 [4121-77-1] Substituted piperazine Serotonin antagonist and...

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Priapism

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antipsychotics (e.g., chlorpromazine, clozapine), antidepressants (most notably trazodone), anti-convulsant and mood stabilizer drugs such as sodium valproate....

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Salbutamol

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Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine...

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Antidepressant

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SARIs belong to the phenylpiperazine class of compounds. They include trazodone and nefazodone. The majority of the tricyclic antidepressants (TCAs) act...

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Aripiprazole

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and is chemically related to cariprazine, nefazodone, etoperidone, and trazodone. It is unusual in having twelve known crystalline polymorphs. Aripiprazole...

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Beta blocker

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Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine...

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