Trazodone

Trazodone
Clinical data
Trade names	Desyrel, Trittico, others
Other names	AF-1161
AHFS/Drugs.com	Monograph
MedlinePlus	a681038
License data	US DailyMed: Trazodone;
Dependence; liability	Low
Addiction; liability	Low–moderate
Routes of; administration	By mouth
ATC code	N06AX05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	By mouth: 65%
Protein binding	89–95%
Metabolism	Liver (CYP3A4, CYP2D6, CYP1A2?)
Metabolites	mCPPTooltip meta-Chlorophenylpiperazine
Onset of action	By mouth: 1 hour (Tmax)
Elimination half-life	• Trazodone (IR): 4–15 hours; • Trazodone (ER): 9–13 hours; • mCPPTooltip meta-Chlorophenylpiperazine: 3–16 hours
Excretion	Urine: 70–75%; Feces: 21%
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 ;
PubChem CID	5533;
IUPHAR/BPS	213;
DrugBank	DB00656 ;
ChemSpider	5332 ;
UNII	YBK48BXK30;
KEGG	D08626 ; as HCl: D00820 ;
ChEBI	CHEBI:9654 ;
ChEMBL	ChEMBL621 ;
CompTox Dashboard (EPA)	DTXSID5045043 ;
ECHA InfoCard	100.039.364
Chemical and physical data
Formula	C19H22ClN5O
Molar mass	371.87 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	87 °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 ; Key:PHLBKPHSAVXXEF-UHFFFAOYSA-N ;
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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 2022, it was the eighteenth most commonly prescribed medication in the United States, with more than 27 million prescriptions.