Trazodone |
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| Trade names | Desyrel, Trittico, others |
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| Other names | AF-1161 |
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| AHFS/Drugs.com | Monograph |
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| MedlinePlus | a681038 |
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| License data |
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Dependence
liability | Low |
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Addiction
liability | None |
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Routes of
administration | By mouth |
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| Drug class | Serotonin antagonist and reuptake inhibitor (SARI); Serotonin 5-HT2A receptor antagonist; α1-Adrenergic receptor antagonist; Serotonin reuptake inhibitor |
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| ATC code | |
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| Legal status |
- AU: S4 (Prescription only)
- BR: Class C1 (Other controlled substances)
- CA: ℞-only
- UK: POM (Prescription only)
- US: ℞-only
- In general: ℞ (Prescription only)
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| Bioavailability | By mouth: 63–80% |
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| Protein binding | 89–95% |
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| Metabolism | Liver (CYP3A4, CYP2D6, CYP1A2?) |
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| Metabolites | mCPPTooltip meta-Chlorophenylpiperazine |
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| Onset of action | By mouth (IR): 1 hour (Tmax) |
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| Elimination half-life | • Trazodone (IR): 4–15 hours
• Trazodone (ER): 9–13 hours
• mCPPTooltip meta-Chlorophenylpiperazine: 3–16 hours |
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| Excretion | Urine: 70–75%
Feces: 21% |
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2-{3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
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| CompTox Dashboard (EPA) | |
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| ECHA InfoCard | 100.039.364 |
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| Formula | C19H22ClN5O |
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| Molar mass | 371.87 g·mol−1 |
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| 3D model (JSmol) | |
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| Melting point | 87 °C (189 °F) |
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Clc4cccc(N3CCN(CCCN1/N=C2/C=C\C=C/N2C1=O)CC3)c4
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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
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Trazodone is an antidepressant medication used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken orally.
Common side effects include dry mouth, feeling faint, vomiting, and headache. More serious side effects may include suicide, mania, irregular heart rate, and pathologically prolonged erections. It is unclear if use during pregnancy or breastfeeding is safe. Trazodone also has sedating effects.
Trazodone was approved for medical use in the United States in 1981. It is available as a generic medication. In 2023, it was the 21st most commonly prescribed medication in the United States and the fifth most common antidepressant, with more than 24 million prescriptions.