{"ATC Code":["N06AX05","N - Nervous system","N06 - Psychoanaleptics","N06A - Antidepressants","N06AX - Other antidepressants","N06AX05 - Trazodone","QN - Nervous system","QN06 - Psychoanaleptics","QN06A - Antidepressants","QN06AX - Other antidepressants","QN06AX05 - Trazodone"],"Abbreviation":["AF-1161"],"Absorption, Distribution and Excretion":"Trazodone is rapidly absorbed in the gastrointestinal tract after oral administration, with a bioavailability ranging from 63-91% and an AUC0−t of 18193.0 ng·h/mL. Food may impact absorption in a variable fashion, and may sometimes lead to decreases in the Cmax of trazodone. In the fed state in 8 healthy volunteers, the Cmax was measured to be 1.47 +/- 0.16 micrograms/mL, and in the fasted state, was measured at 1.88 +/- 0.42 micrograms/mL. The average Tmax after a single dose of 300 mg was 8 hours. Food may increase absorption by up to 20%.","Adverse Effects":"The primary adverse effects of trazodone include headaches, fatigue, dizziness, drowsiness, and somnolence. Other risks include anticholinergic effects (dry mouth), orthostatic hypotension, syncope, QT prolongation, Torsade de pointes, priapism, and increased suicidal thoughts. QT prolongation and arrhythmia risks are due to the interaction of trazodone with hERG potassium channels.","Aliases":["Trazodone","Trazodon","Beneficat","Trazalon","Trazodil","Trazodona","Trazonil","Trittico","Desirel","Sideril","Trazodonum","Desyrel Dividose","1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-","J10.767K","1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-","CHEBI:9654","Dtxsid5045043","s-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-","Tradozone","2-(3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one","2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one","RatioTrazodone","ratio Trazodone","Novo Trazodone","Apo Trazodone","Gen Trazodone","Nu Trazodone","PMS Trazodone","2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)(1,2,4)triazolo(4,3-a)pyridin-3(2H)-one","2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-(1,2,4)triazolo(4,5-a)pyridin-3-one","2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,5-a]pyridin-3-one","TrazodonNeuraxpharm","2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-2H,3H-(1,2,4)triazolo(4,3-a)pyridin-3-one","Trazodon neuraxpharm","Dtxcid3025043","N06AX05","243-317-1","Molipaxin","Trazodone free base","2-(3-(4-(3-Chlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one","CHEMBL621","2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one","Ncgc00016035-02","Einecs 243-317-1","Cas-25332-39-2","Unii-ybk48bxk30","Brn 0628010","Spectrum_001424","Prestwick0_000292","Prestwick1_000292","Prestwick2_000292","Prestwick3_000292","Spectrum2_000854","Spectrum3_001560","Spectrum4_000755","Spectrum5_000974","Lopac-T-6154","Ec 243-317-1","Lopac0_001159","Oprea1_185901","Schembl28167","BSPBio_000224","BSPBio_003040","GTPL213","KBioGR_001110","KBioSS_001904","DivK1c_000196","SPBio_000867","SPBio_002443","BPBio1_000248","HY-B0478AR","orb1305920","Schembl29390760","HSDB 7048","HY-B0478A","KBio1_000196","KBio2_001904","KBio2_004472","KBio2_007040","KBio3_002540","Ninds_000196","HMS5085D13","Trazodone Hydrochloride Impurity 30","Bdbm50073444","EBC-26833","Mfcd00242886","s5857","Akos015896423","AC-6778","CCG-205233","DB00656","FT40163","Sdccgsbi-0051126.p004","1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-,","Idi1_000196","Ncgc00016035-01","Ncgc00016035-03","Ncgc00016035-04","Ncgc00016035-05","Ncgc00016035-06","Ncgc00016035-07","Ncgc00016035-08","Ncgc00016035-09","Ncgc00016035-10","Ncgc00016035-12","Ncgc00016035-25","Ncgc00024405-03","8-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-1,7,8-triazabicyclo[4.3.0]nona-2,4,6-trien-9-one hydrochloride","DA-58707","Sbi-0051126.p003","CS-0009580","NS00010404","C07156","D08626","En300-708789","H37050","Ab00053648-14","Ab00053648_15","Ab00053648_16","L000771","Brd-k70778732-003-05-1","Brd-k70778732-003-15-0","Brd-k70778732-003-26-7","Brd-k70778732-003-27-5","2-(3-(4-(M-chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2h)-one","2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-2-ium-3-olate","2-(3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one #"],"Biological Half-Life":"The plasma elimination half-life was markedly prolonged (13.6 versus 6 hours) elderly volunteers in the fasted state when compared with younger volunteers. Another study of 8 healthy individuals taking a single dose of trazodone indicated a terminal elimination half-life of 7.3 +/- 0.8 hr.   A two-phase pattern of trazodone elimination has been reported. Initially, the half-life is reported to range from 3 to 6 hours and the second phase of elimination to range from 5 to 9 hours.","CAS":"19794-93-5","ChemicalClasses":["phenylpiperazine"],"Chirality":"achiral","Color/Form":"Crystals","Decomposition":"When heated to decomposition it emits toxic fumes of /chlorides, hydrogen chloride and nitrogen oxides/.","Drug Classes":["Breast Feeding","Lactation","Milk, Human","Antidepressive Agents","Serotonin Uptake Inhibitors"],"Drug Indication":"Trazodone is indicated for the treatment of major depressive disorder (MDD). It has been used off-label for adjunct therapy in alcohol dependence, and off-label to treat anxiety and insomnia. It may also be used off-label to treat symptoms of dementia, Alzheimer’s disease, schizophrenia, eating disorders, and fibromyalgia due to its effects on various neurotransmitter receptors.","Drug Warnings":"/BOXED WARNING/ WARNING: SUICIDALITY AND ANTIDEPRESSANT DRUGS. Antidepressants increased the risk compared to placebo of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults in short-term studies of major depressive disorder (MDD) and other psychiatric disorders. Anyone considering the use of trazodone hydrochloride tablets or any other antidepressant in a child, adolescent, or young adult must balance this risk with the clinical need. Short-term studies did not show an increase in the risk of suicidality with antidepressants compared to placebo in adults beyond age 24; there was a reduction in risk with antidepressants compared to placebo in adults aged 65 and older. Depression and certain other psychiatric disorders are themselves associated with increases in the risk of suicide. Patients of all ages who are started on antidepressant therapy should be monitored appropriately and observed closely for clinical worsening, suicidality, or unusual changes in behavior. Families and caregivers should be advised of the need for close observation and communication with the prescriber. Trazodone hydrochloride tablets are not approved for use in pediatric patients.","EliminationHalfLife":"• Trazodone (immediate-release): 4 – 15 hours• Trazodone (extended-release): 9 – 13 hours• meta-Chlorophenylpiperazine: 3 – 16 hours\u003ca href='#cite_note-4'\u003e\u003csup\u003e[4]\u003c/sup\u003e\u003c/a\u003e","Esters":[],"European Community (EC) Number":"243-317-1","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"YBK48BXK30"}]}},{"Name":"Active Moiety","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"TRAZODONE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Established Pharmacologic Class [EPC] - Serotonin Reuptake Inhibitor"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5533","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Trazodone"},{"Extra":"CID-5202","Length":9,"Start":15,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Trazodone is a Serotonin Reuptake Inhibitor."}]}}],"Formating":[],"HMDB ID":"HMDB0014794","HeavyAtomCount":26,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Antidepressive Agents; Serotonin Uptake Inhibitors","IUPACName":"2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one","Impurities":"...1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine HCl (CCP HCl) a process related impurity in trazodone. /Genotoxic Impurity/","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","InChIKey":"PHLBKPHSAVXXEF-UHFFFAOYSA-N","Interactions":"Concomitant use of trazodone with inhibitors of CYP3A4 can result in substantially increased plasma concentrations of trazodone and increase the potential for adverse effects. In one study, concomitant use of ritonavir (200 mg twice daily for 2 days) and trazodone (a single 50-mg dose) in healthy individuals increased maximum plasma concentrations and decreased clearance of trazodone by 34 and 52%, respectively, and increased area under the plasma concentration-time curve (AUC) and half-life of trazodone by greater than twofold. Adverse effects (e.g., nausea, hypotension, syncope) also were observed with concomitant use of trazodone and ritonavir. The manufacturers of trazodone state that a reduction in trazodone dosage should be considered in patients receiving a potent inhibitor of the CYP3A4 isoenzyme (e.g., indinavir, itraconazole, ketoconazole, nefazodone, ritonavir) concomitantly with trazodone.","KEGG Entries":[{"Id":"D00820","Interactions":[{"Action":"inhibition","Target":"CYP3A4"},{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone hydrochloride","Desyrel"]},{"Id":"D08626","Interactions":[{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone","Trittico"]},{"Id":"D00820","Interactions":[{"Action":"inhibition","Target":"CYP3A4"},{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone hydrochloride","Desyrel"]},{"Id":"D08626","Interactions":[{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone","Trittico"]},{"Id":"D00820","Interactions":[{"Action":"inhibition","Target":"CYP3A4"},{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone hydrochloride","Desyrel"]},{"Id":"D08626","Interactions":[{"Action":"induction","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP3A4"},{"Action":"inhibition","Target":"CYP2D6"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Trazodone","Trittico"]}],"MeSH Headers":[{"Id":"M0021855","Link":"https://id.nlm.nih.gov/mesh/M0021855.html","Name":"Trazodone","Ref":108},{"Id":"M0021854","Link":"https://id.nlm.nih.gov/mesh/M0021854.html","Name":"Trittico","Ref":110},{"Id":"M0361360","Link":"https://id.nlm.nih.gov/mesh/M0361360.html","Name":"Molipaxin","Ref":111},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":112},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":138},{"Id":"M0021771","Link":"https://id.nlm.nih.gov/mesh/M0021771.html","Name":"Anti-Anxiety Agents","Ref":139},{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":140},{"Id":"M0556972","Link":"https://id.nlm.nih.gov/mesh/M0556972.html","Name":"Selective Serotonin Reuptake Inhibitors","Ref":141}],"MeSH Pharmacological Classification":[{"Id":"M0021771","Link":"https://id.nlm.nih.gov/mesh/M0021771.html","Name":"Anti-Anxiety Agent","Ref":139},{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":140},{"Id":"M0556972","Link":"https://id.nlm.nih.gov/mesh/M0556972.html","Name":"Selective Serotonin Reuptake Inhibitor","Ref":141}],"Mechanism of Action":"The mechanism of action of trazodone is not fully understood, however, it is known to inhibit the reuptake of serotonin and block both histamine and alpha-1-adrenergic receptors.  Despite the fact that trazodone is frequently considered a selective serotonin reuptake inhibitor, several reports have shown that other mechanisms including antagonism at serotonin 5-HT1a, 5-HT1c, and 5-HT2 receptor subtypes may occur. The strongest antagonism of trazodone is reported to occur at the serotonin  5-HT21c receptors, preventing serotonin uptake. In addition to acting on serotonin receptors, trazodone has been shown to inhibit serotonin transporters.  The antidepressant effects of trazodone result from the inhibition of receptor uptake, which normally decreases circulating neurotransmitters, contributing to depressive symptoms.","Melting Point":"231-234","Metabolism/Metabolites":"Trazodone is heavily metabolized and activated in the liver by CYP3A4 enzyme to the active metabolite, m-chlorophenylpiperazine (mCPP). The full metabolism of trazodone has not been well characterized. Some other metabolites that have been identified are a dihydrodiol metabolite and carboxylic acid.","MolecularFormula":"C\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eClN\u003csub\u003e5\u003c/sub\u003eO","MolecularWeight":"371.9 g/mol","Non-Human Toxicity Values":"LD50 Rat oral 690 mg/kg","Pharmacodynamics":"Trazodone treats depressed mood and other depression-related symptoms and shows benefit in the treatment of insomnia due to its sedating effects. It is known to prolong the cardiac QT-interval. Memory, alertness, and cognition may be decreased by trazodone, especially in elderly patients due to its central nervous system depressant effects.  A note on priapism  Trazodone has been associated with the occurrence of priapism, a painful and persistent incidence of penile tissue erection that is unrelievable and can cause permanent neurological damage if left untreated. Patients must be advised to seek immediate medical attention if priapism is suspected.","Physical Description":"Solid","PubChemId":5533,"Record Description":["LiverTox|CNS|Antidepressant|SNRI"],"Records":{"UNII":{"Impurities":["isotrazodone"]}},"RefChem":"56148","RefCount":5,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Trazodone","Name":"Trazodone","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q411457","Name":"Trazodone","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00656","Name":"Trazodone","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5533","Name":"Trazodone","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=19794-93-5","Name":"Trazodone","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014794","Name":"Trazodone","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07156","Name":"Trazodone","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/YBK48BXK30","Name":"Trazodone","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID5045043","Name":"Trazodone","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5533, Trazodone. Accessed April 16, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5533\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5533\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Trazodone. UNII: YBK48BXK30. Global Substance Registration System. Accessed April 16, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/YBK48BXK30\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/YBK48BXK30\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed April 16, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e","Schatzberg AF, Nemeroff CB. The American Psychiatric Association Publishing Textbook of Psychopharmacology. American Psychiatric Pub. 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3.717M138.54 35.443l-.392-3.716M55.007 41.229l-5.023 2.9\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m6.875 40.275 5.843 3.373\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"mol\"\u003e\u003cg fill=\"#1ff01f\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M204.992 33.616q-.786 0-1.238.53-.453.524-.453 1.446 0 .911.417 1.447.423.53 1.268.53.322 0 .607-.054.292-.059.566-.143v.536q-.274.101-.566.149-.291.054-.696.054-.744 0-1.25-.31-.5-.31-.75-.875-.25-.572-.25-1.34 0-.744.267-1.309.274-.566.804-.881.53-.322 1.28-.322.78 0 1.351.286l-.244.524q-.226-.101-.506-.185-.274-.083-.607-.083m2.757 4.423h-.602v-5.215h.602zM202.085 38.039h-.619v-2.286h-2.512v2.286h-.614V33.14h.614v2.071h2.512V33.14h.619z\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Trazodone hydrochloride","UNII":"6E8ZO8LRNM"}],"Salts":["hydrochloride"],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S4 substance"},{"gov":"Brazil","ref":["3"],"schedule":"C1 substance"},{"gov":"Canada","ref":[],"schedule":"prescription only substance"},{"gov":"United Kingdom","ref":[],"schedule":"prescription only substance"},{"gov":"United States","ref":[],"schedule":"prescription only substance"}],"Solubility":"2.90e-01 g/L","Stability/Shelf Life":"Stable under recommended storage conditions. /Trazadone hydrochloride/","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 185.4 70.935\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h186v71H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m84.562 39.417-13.198 7.62M71.364 47.037l-10.05-5.807M58.159 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26.123l-3.682-4.065M164.826 29.305l5.954.002M159.371 32.966l-2.753 4.768M137.756 28.01l.392 3.717M138.54 35.443l-.392-3.716M55.007 41.229l-5.023 2.9\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m6.875 40.275 5.843 3.373\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Anti-Anxiety Agents; Antidepressive Agents, Second-Generation; Serotonin Uptake Inhibitors","Title":"Trazodone","Toxicity Data":"LD50: 96mg/kg (Intravenous, Mouse) (A308)","Treatment":"There is no specific antidote for Trazodone. Treatment should be symptomatic and supportive in the case of hypotension or excessive sedation. Any patient suspected of having taken an overdose should have the stomach emptied by gastric lavage. Forced diuresis may be useful in facilitating elimination of the drug. (L1712)","UNII":"YBK48BXK30","Wikidata":"Q411457","Wikipedia":"Trazodone","XLogP":2.8}