Identification
- Summary
Trazodone is a serotonin uptake inhibitor used to treat major depressive disorder.
- Brand Names
- Desyrel, Oleptro
- Generic Name
- Trazodone
- DrugBank Accession Number
- DB00656
- Background
Trazodone is triazolopyridine derivative from the serotonin receptor antagonists and reuptake inhibitors (SARIs) class of antidepressants.11 It is used in adults and has been shown to be comparable in efficacy to other drugs such as tricyclic antidepressants (TCAs), selective serotonin reuptake inhibitors (SSRIs), and serotonin-norepinephrine receptor inhibitor (SNRIs) in the treatment of depression.20 A unique feature of this drug is that it does not promote the anxiety symptoms, sexual symptoms, or insomnia, which are commonly associated with SSRI and SNRI therapy.20 Trazodone acts on various receptors, including certain histamine, serotonin, and adrenergic receptors, distinguishing it from other antidepressants that cover a narrow range of neurotransmitters.20 It was initially granted FDA approval in 1981.21
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Trazodone (DB00656)
- Weight
- Average: 371.864
Monoisotopic: 371.151288058 - Chemical Formula
- C19H22ClN5O
- Synonyms
- 2-(3-[4-(3-chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
- Trazodona
- Trazodone
- Trazodonum
- External IDs
- J10.767K
Pharmacology
- Indication
Trazodone is indicated for the treatment of major depressive disorder (MDD).21 It has been used off-label for adjunct therapy in alcohol dependence, and off-label to treat anxiety and insomnia.21 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.10
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in management of Alcohol dependence ••• ••••• Management of Alzheimer's disease ••• ••••• Treatment of Anxiety ••• ••••• Treatment of Dementia ••• ••••• Treatment of Eating disorders symptoms ••• ••••• - Contraindications & Blackbox Warnings
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Trazodone treats depressed mood and other depression-related symptoms and shows benefit in the treatment of insomnia due to its sedating effects.20 It is known to prolong the cardiac QT-interval.21 Memory, alertness, and cognition may be decreased by trazodone, especially in elderly patients due to its central nervous system depressant effects.9
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.15,21
- 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.20 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.9,20 The strongest antagonism of trazodone is reported to occur at the serotonin 5-HT21c receptors, preventing serotonin uptake.1 In addition to acting on serotonin receptors, trazodone has been shown to inhibit serotonin transporters.18,19 The antidepressant effects of trazodone result from the inhibition of receptor uptake, which normally decreases circulating neurotransmitters, contributing to depressive symptoms.13,14
Target Actions Organism A5-hydroxytryptamine receptor 2A antagonistHumans A5-hydroxytryptamine receptor 2C agonistHumans ASodium-dependent serotonin transporter inhibitorHumans A5-hydroxytryptamine receptor 1A antagonistpartial agonistHumans UHistamine H1 receptor antagonistHumans NAlpha-1A adrenergic receptor antagonistHumans NAlpha-2A adrenergic receptor antagonistHumans U5-hydroxytryptamine receptor 1C antagonistpartial agonistRat - Absorption
Trazodone is rapidly absorbed in the gastrointestinal tract after oral administration, with a bioavailability ranging from 63-91% 9 and an AUC0−t of 18193.0 ng·h/mL.17 Food may impact absorption in a variable fashion, and may sometimes lead to decreases in the Cmax of trazodone.9,16 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%.25
- Volume of distribution
A single-dose pharmacokinetic study of 8 volunteers taking trazodone determined a volume of distribution of 0.84 +/- 0.16 L/kg.16 The FDA medical review of trazodone reports a volume of distribution of 0.47 to 0.84 L/kg.25
- Protein binding
The plasma protein binding of trazodone is 89-95% according to in vitro studies.22
- Metabolism
Trazodone is heavily metabolized and activated in the liver by CYP3A4 enzyme to the active metabolite, m-chlorophenylpiperazine (mCPP).3,4 The full metabolism of trazodone has not been well characterized.22 Some other metabolites that have been identified are a dihydrodiol metabolite and carboxylic acid.2
Hover over products below to view reaction partners
- Route of elimination
Less than 1% of an oral dose is excreted unchanged in the urine.22 In a pharmacokinetic study, about 60-70% of radiolabeled was excreted urine within 48 hours. Approximately 9-29% was found to be excreted in feces over a range of 60 to 100 hours.22 According to the FDA medical review, the kidneys are responsible for 70 to 75% of trazodone excretion. About 21% of trazodone is reported to be excreted by the fecal route and 0.13% of the parent drug is eliminated in the urine as unchanged drug.25
- 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.9 Another study of 8 healthy individuals taking a single dose of trazodone indicated a terminal elimination half-life of 7.3 +/- 0.8 hr.16
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.25
- Clearance
A decrease in total apparent clearance (5.1 versus 10.8 L/h) was seen elderly volunteers in the fasted state when compared with younger volunteers.9 Another pharmacokinetic study determined the total body clearance of trazodone to be 5.3 +/- 0.9 L/hr in 8 healthy patients taking a single dose of trazodone.16
- Adverse Effects
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The oral LD50 of trazodone is 690 mg/kg in rats.22
An overdose of trazodone may result in central nervous system, cardiac, respiratory effects. Signs and symptoms may include dyspnea, bradycardia, hypotension, mental status changes, lack of coordination, and coma, among others.23 In addition, an overdose may result in priapism, a persistent unrelievable penile tissue erection that may cause permanent damage if not treated promptly.15 No specific antidote exists for a trazodone overdose. If an overdose occurs, consider the possibility that trazodone may have been combined with other drugs. Contact a poison control center in case of overdose for the most current management guidelines.21 Dialysis does not accelerate trazodone clearance.9
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Trazodone. Abametapir The serum concentration of Trazodone can be increased when it is combined with Abametapir. Abatacept The metabolism of Trazodone can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Trazodone is combined with Abciximab. Abemaciclib The serum concentration of Abemaciclib can be decreased when it is combined with Trazodone. - Food Interactions
- Avoid alcohol.
- Avoid St. John's Wort. The risk of serotonin syndrome may be increased.
- Take after a meal. Should be taken shortly after a light meal or snack.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Trazodone hydrochloride 6E8ZO8LRNM 25332-39-2 OHHDIOKRWWOXMT-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Beneficat / Deprax / Desirel / Desyrel Dividose (Bristol-Myers Squibb) / Mesyrel / Molipaxin / Thombran / Trialodine / Trittico
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desyrel Tablet 100 mg/1 Oral Pragma Pharmaceuticals, LLC 2022-07-01 Not applicable US 
Desyrel Tablet 300 mg/1 Oral Bristol Myers Squibb 2007-01-01 2008-11-30 US Desyrel Tablet 300 mg/1 Oral Pragma Pharmaceuticals, LLC 2022-07-01 Not applicable US Desyrel Tablet 50 mg/1 Oral Pragma Pharmaceuticals, LLC 2022-07-01 Not applicable US Desyrel Tablet 150 mg/1 Oral Bristol Myers Squibb 2007-01-01 2008-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-trazodone Tablet 100 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada 
Ag-trazodone Tablet 50 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Ag-trazodone Tablet 150 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Apo-trazodone D Tablets 150mg Tablet 150 mg Oral Apotex Corporation 1995-12-31 Not applicable Canada Apo-trazodone Tablets 100mg Tablet 100 mg Oral Apotex Corporation 1995-12-31 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Trazamine Trazodone hydrochloride (50 mg/1) + Choline (250 mg/1) Kit Oral Physician Therapeutics Llc 2011-02-03 Not applicable US
Categories
- ATC Codes
- N06AX05 — Trazodone
- Drug Categories
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Anti-Anxiety Agents
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Antidepressive Agents, Second-Generation
- Antidepressive Agents, Triazolopyridine
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Histamine Antagonists
- Histamine H1 Antagonists
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- P-glycoprotein inducers
- Peripheral alpha-1 blockers
- Piperazines
- Potential QTc-Prolonging Agents
- Psychoanaleptics
- Psychotropic Drugs
- Pyridines
- Pyridones
- QTc Prolonging Agents
- Selective Serotonin Reuptake Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Antagonists
- Serotonin 5-HT1A Receptor Antagonists
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin antagonist and reuptake inhibitors (SARIs)
- Serotonin Modulators
- Serotonin Receptor Antagonists
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Phenylpiperazines
- Alternative Parents
- N-arylpiperazines / Aryl 1,2,4-triazolones / Triazolopyridines / Aniline and substituted anilines / Dialkylarylamines / Pyridinones / Chlorobenzenes / N-alkylpiperazines / Aryl chlorides / Heteroaromatic compounds show 7 more
- Substituents
- 1,2,4-triazole / Amine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl 1,2,4-triazol-3-one / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- N-arylpiperazine, monochlorobenzenes, N-alkylpiperazine, triazolopyridine (CHEBI:9654)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- YBK48BXK30
- CAS number
- 19794-93-5
- InChI Key
- PHLBKPHSAVXXEF-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one
- SMILES
- ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1
References
- General References
- Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [Article]
- Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)]. Arzneimittelforschung. 1976;26(11):2084-9. [Article]
- Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [Article]
- Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [Article]
- Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. [Article]
- Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. [Article]
- Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. [Article]
- Davis JL, Schirmer J, Medlin E: Pharmacokinetics, pharmacodynamics and clinical use of trazodone and its active metabolite m-chlorophenylpiperazine in the horse. J Vet Pharmacol Ther. 2018 Jun;41(3):393-401. doi: 10.1111/jvp.12477. Epub 2018 Jan 14. [Article]
- Haria M, Fitton A, McTavish D: Trazodone. A review of its pharmacology, therapeutic use in depression and therapeutic potential in other disorders. Drugs Aging. 1994 Apr;4(4):331-55. doi: 10.2165/00002512-199404040-00006. [Article]
- Fagiolini A, Comandini A, Catena Dell'Osso M, Kasper S: Rediscovering trazodone for the treatment of major depressive disorder. CNS Drugs. 2012 Dec;26(12):1033-49. doi: 10.1007/s40263-012-0010-5. [Article]
- Mandrioli R, Protti M, Mercolini L: New-Generation, Non-SSRI Antidepressants: Therapeutic Drug Monitoring and Pharmacological Interactions. Part 1: SNRIs, SMSs, SARIs. Curr Med Chem. 2018;25(7):772-792. doi: 10.2174/0929867324666170712165042. [Article]
- Jaffer KY, Chang T, Vanle B, Dang J, Steiner AJ, Loera N, Abdelmesseh M, Danovitch I, Ishak WW: Trazodone for Insomnia: A Systematic Review. Innov Clin Neurosci. 2017 Aug 1;14(7-8):24-34. eCollection 2017 Jul-Aug. [Article]
- Blier P: Neurotransmitter targeting in the treatment of depression. J Clin Psychiatry. 2013;74 Suppl 2:19-24. doi: 10.4088/JCP.12084su1c.04. [Article]
- Nutt DJ: Relationship of neurotransmitters to the symptoms of major depressive disorder. J Clin Psychiatry. 2008;69 Suppl E1:4-7. [Article]
- Hoffmann P, Neu ET, Neu D: Penile amputation after trazodone-induced priapism: a case report. Prim Care Companion J Clin Psychiatry. 2010;12(2). doi: 10.4088/PCC.09l00816gry. [Article]
- Nilsen OG, Dale O: Single dose pharmacokinetics of trazodone in healthy subjects. Pharmacol Toxicol. 1992 Aug;71(2):150-3. [Article]
- Kale P, Agrawal YK: Pharmacokinetics of single oral dose trazodone: a randomized, two-period, cross-over trial in healthy, adult, human volunteers under fed condition. Front Pharmacol. 2015 Oct 2;6:224. doi: 10.3389/fphar.2015.00224. eCollection 2015. [Article]
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Stahl SM: Mechanism of action of trazodone: a multifunctional drug. CNS Spectr. 2009 Oct;14(10):536-46. [Article]
- Justin J. Shin; Abdolreza Saadabadi. (2019). Trazodone, StatPearls. Stat Pearls.
- Trazodone [Link]
- Monograph, Trazodone [Link]
- Trazodone overdose, NIH Medline [Link]
- Rapid structure determination of microgram-level drug metabolites using HPLC-MS, fraction collection and NMR spectroscopy [Link]
- FDA application review, Trazodone [Link]
- External Links
- Human Metabolome Database
- HMDB0014794
- KEGG Drug
- D08626
- KEGG Compound
- C07156
- PubChem Compound
- 5533
- PubChem Substance
- 46506648
- ChemSpider
- 5332
- BindingDB
- 50073444
- 10737
- ChEBI
- 9654
- ChEMBL
- CHEMBL621
- ZINC
- ZINC000000538483
- Therapeutic Targets Database
- DAP000104
- PharmGKB
- PA451744
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Trazodone
- MSDS
- Download (73.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Insomnia Chronic 1 4 Completed Treatment Cerebral Infarctions / Sleep Apnea 1 4 Completed Treatment Fibromyalgia 1 4 Completed Treatment Schizophrenia 1 4 Not Yet Recruiting Treatment Delirium / Morality / Psych / Quality of Life (QOL) / Treatment Side Effects 1
Pharmacoeconomics
- Manufacturers
- Labopharm inc
- Apothecon inc div bristol myers squibb
- Alvogen inc
- American therapeutics inc
- Apotex inc
- Matrix laboratories ltd
- Mutual pharmaceutical co inc
- Mylan pharmaceuticals inc
- Pliva inc
- Quantum pharmics ltd
- Sandoz inc
- Teva pharmaceuticals usa inc
- Usl pharma inc
- Vintage pharmaceuticals llc
- Watson laboratories inc
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Apotex Inc.
- Apothecon
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Barr Pharmaceuticals
- Bristol-Myers Squibb Co.
- Bryant Ranch Prepack
- Cardinal Health
- Caremark LLC
- Corepharma LLC
- Coupler Enterprises Inc.
- DHHS Program Support Center Supply Service Center
- Direct Dispensing Inc.
- DispenseXpress Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Golden State Medical Supply Inc.
- Goldline Laboratories Inc.
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Innoviant Pharmacy Inc.
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- Labopharm Inc.
- Lake Erie Medical and Surgical Supply
- Letco Medical Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Mckesson Corp.
- Medisca Inc.
- Medvantx Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Mylan
- Neighborcare Repackaging Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharma Pac LLC
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmacy Service Center
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescription Dispensing Service Inc.
- Qualitest
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandhills Packaging Inc.
- Shanghai World Prospect Industrial Co. Ltd.
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Rx Usa
- Teva Pharmaceutical Industries Ltd.
- United Research Laboratories Inc.
- Va Cmop Dallas
- Vangard Labs Inc.
- Dosage Forms
Form Route Strength Tablet Oral 150 mg Capsule Oral 100 mg Capsule Oral 50 mg Tablet Oral 300 mg/1 Tablet Oral Tablet Oral 300 mg / tab Tablet, film coated Oral Tablet, extended release Oral 150 mg Tablet, extended release Oral 150 mg/1 Tablet, extended release Oral 300 mg/1 Tablet, extended release Oral 300 mg Tablet Oral 150 mg / tab Tablet Oral 100 mg Tablet Oral 75 mg Tablet Oral 100 mg / tab Tablet Oral 50 mg / tab Capsule Oral 50.000 mg Solution Intramuscular; Intravenous 100 mg Solution Oral 100 mg Kit Oral Tablet Oral 5000000 mg Tablet, coated Oral 50 mg Powder Not applicable 1 kg/1kg Tablet Oral 100 mg/1 Tablet Oral 100 mg/301 Tablet Oral 150 mg/1 Tablet Oral 50 mg/1 Tablet Oral 50 mg/301 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 50 mg/1 Injection, solution 50 MG/5ML Injection, solution 67.2 MG/100ML Solution / drops Oral 25 MG/ML Solution / drops Oral 60 MG/ML Tablet Oral 25 MG Tablet, extended release Oral 75 MG Tablet, film coated Oral 150 MG Tablet, film coated Oral 300 MG Tablet, coated Oral 100 mg Tablet, coated Oral 10000000 mg Tablet Oral 68.25 mg Tablet Oral 50 mg Tablet, film coated Oral 100 mg Tablet, film coated Oral 50 mg - Prices
Unit description Cost Unit Trazodone hcl powder 8.26USD g Desyrel 300 mg tablet 6.03USD tablet TraZODone HCl 300 mg tablet 5.65USD tablet Trazodone 300 mg tablet 5.44USD tablet Desyrel 100 mg tablet 4.6USD tablet Desyrel 150 mg tablet 3.39USD tablet TraZODone HCl 150 mg tablet 1.53USD tablet Trazodone 150 mg tablet 1.47USD tablet Desyrel 50 mg tablet 1.33USD tablet TraZODone HCl 100 mg tablet 0.76USD tablet Trazodone 100 mg tablet 0.73USD tablet Apo-Trazodone D 150 mg Tablet 0.61USD tablet Desyrel Dividose 150 mg Tablet 0.61USD tablet Novo-Trazodone 150 mg Tablet 0.61USD tablet Nu-Trazodone-D 150 mg Tablet 0.61USD tablet Ratio-Trazodone 150 mg Tablet 0.61USD tablet TraZODone HCl 50 mg tablet 0.59USD tablet Trazodone 50 mg tablet 0.57USD tablet Nu-Trazodone 100 mg Tablet 0.41USD tablet Pms-Trazodone 100 mg Tablet 0.41USD tablet Ratio-Trazodone 100 mg Tablet 0.41USD tablet Apo-Trazodone 100 mg Tablet 0.41USD tablet Desyrel 100 mg Tablet 0.41USD tablet Mylan-Trazodone 100 mg Tablet 0.41USD tablet Novo-Trazodone 100 mg Tablet 0.41USD tablet Pms-Trazodone 75 mg Tablet 0.34USD tablet Apo-Trazodone 50 mg Tablet 0.23USD tablet Mylan-Trazodone 50 mg Tablet 0.23USD tablet Novo-Trazodone 50 mg Tablet 0.23USD tablet Nu-Trazodone 50 mg Tablet 0.23USD tablet Pms-Trazodone 50 mg Tablet 0.23USD tablet Ratio-Trazodone 50 mg Tablet 0.23USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8133893 No 2012-03-13 2029-03-13 US US6607748 No 2003-08-19 2020-06-29 US US7829120 No 2010-11-09 2027-03-27 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 231-234 https://pdf.hres.ca/dpd_pm/00007839.PDF boiling point (°C) 528.5 https://www.lookchem.com/Trazodone/ logP 2.68 http://www.t3db.ca/toxins/T3D2852 logS -3.1 http://www.t3db.ca/toxins/T3D2852 pKa 6.74 https://patents.google.com/patent/EP1931346B1 - Predicted Properties
Property Value Source Water Solubility 0.29 mg/mL ALOGPS logP 2.68 ALOGPS logP 3.13 Chemaxon logS -3.1 ALOGPS pKa (Strongest Basic) 7.09 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 42.39 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 105.88 m3·mol-1 Chemaxon Polarizability 40.12 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9829 Caco-2 permeable - 0.6166 P-glycoprotein substrate Substrate 0.547 P-glycoprotein inhibitor I Inhibitor 0.8634 P-glycoprotein inhibitor II Inhibitor 0.8889 Renal organic cation transporter Inhibitor 0.6479 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.6613 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.83 Ames test Non AMES toxic 0.5133 Carcinogenicity Non-carcinogens 0.8545 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7007 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.8994 hERG inhibition (predictor II) Inhibitor 0.7503
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 198.5422335 predictedDarkChem Lite v0.1.0 [M-H]- 179.68797 predictedDeepCCS 1.0 (2019) [M+H]+ 198.9979335 predictedDarkChem Lite v0.1.0 [M+H]+ 182.04594 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.6221335 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.63182 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Pazzagli M, Giovannini MG, Pepeu G: Trazodone increases extracellular serotonin levels in the frontal cortex of rats. Eur J Pharmacol. 1999 Nov 3;383(3):249-57. doi: 10.1016/s0014-2999(99)00644-5. [Article]
- Marcoli M, Rosu C, Bonfanti A, Raiteri M, Maura G: Inhibitory presynaptic 5-hydroxytryptamine(2A) receptors regulate evoked glutamate release from rat cerebellar mossy fibers. J Pharmacol Exp Ther. 2001 Dec;299(3):1106-11. [Article]
- Luparini MR, Garrone B, Pazzagli M, Pinza M, Pepeu G: A cortical GABA-5HT interaction in the mechanism of action of the antidepressant trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Nov;28(7):1117-27. [Article]
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Balsara JJ, Jadhav SA, Gaonkar RK, Gaikwad RV, Jadhav JH: Effects of the antidepressant trazodone, a 5-HT 2A/2C receptor antagonist, on dopamine-dependent behaviors in rats. Psychopharmacology (Berl). 2005 May;179(3):597-605. doi: 10.1007/s00213-004-2095-0. Epub 2004 Dec 22. [Article]
- Stryjer R, Strous RD, Bar F, Poyurovsky M, Weizman A, Kotler M: Treatment of neuroleptic-induced akathisia with the 5-HT2A antagonist trazodone. Clin Neuropharmacol. 2003 May-Jun;26(3):137-41. [Article]
- Trazodone [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
- Fiorella D, Rabin RA, Winter JC: The role of the 5-HT2A and 5-HT2C receptors in the stimulus effects of m-chlorophenylpiperazine. Psychopharmacology (Berl). 1995 May;119(2):222-30. [Article]
- Conn PJ, Sanders-Bush E: Relative efficacies of piperazines at the phosphoinositide hydrolysis-linked serotonergic (5-HT-2 and 5-HT-1c) receptors. J Pharmacol Exp Ther. 1987 Aug;242(2):552-7. [Article]
- Pazzagli M, Giovannini MG, Pepeu G: Trazodone increases extracellular serotonin levels in the frontal cortex of rats. Eur J Pharmacol. 1999 Nov 3;383(3):249-57. doi: 10.1016/s0014-2999(99)00644-5. [Article]
- Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [Article]
- Balsara JJ, Jadhav SA, Gaonkar RK, Gaikwad RV, Jadhav JH: Effects of the antidepressant trazodone, a 5-HT 2A/2C receptor antagonist, on dopamine-dependent behaviors in rats. Psychopharmacology (Berl). 2005 May;179(3):597-605. doi: 10.1007/s00213-004-2095-0. Epub 2004 Dec 22. [Article]
- Trazodone [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Stahl SM: Mechanism of action of trazodone: a multifunctional drug. CNS Spectr. 2009 Oct;14(10):536-46. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistPartial agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Odagaki Y, Toyoshima R, Yamauchi T: Trazodone and its active metabolite m-chlorophenylpiperazine as partial agonists at 5-HT1A receptors assessed by [35S]GTPgammaS binding. J Psychopharmacol. 2005 May;19(3):235-41. [Article]
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Subhash MN, Srinivas BN, Vinod KY: Alterations in 5-HT(1A) receptors and adenylyl cyclase response by trazodone in regions of rat brain. Life Sci. 2002 Aug 16;71(13):1559-67. [Article]
- Sultan MA, Courtney DB: Adjunctive Trazodone and Depression Outcome in Adolescents Treated with Serotonin Re-uptake Inhibitors. J Can Acad Child Adolesc Psychiatry. 2017 Fall;26(3):233-240. Epub 2017 Oct 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [Article]
- Noguchi S, Inukai T, Kuno T, Tanaka C: The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking. Physiol Behav. 1992 Jun;51(6):1123-7. [Article]
- Justin J. Shin; Abdolreza Saadabadi. (2019). Trazodone, StatPearls. Stat Pearls.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Ashford JW: Treatment of Alzheimer's Disease: Trazodone, Sleep, Serotonin, Norepinephrine, and Future Directions. J Alzheimers Dis. 2019;67(3):923-930. doi: 10.3233/JAD-181106. [Article]
- Justin J. Shin; Abdolreza Saadabadi. (2019). Trazodone, StatPearls. Stat Pearls.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [Article]
- Price LH, Charney DS, Heninger GR: Effects of trazodone treatment on alpha-2 adrenoceptor function in depressed patients. Psychopharmacology (Berl). 1986;89(1):38-44. [Article]
- Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- Unknown
- Actions
- AntagonistPartial agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- Htr2c
- Uniprot ID
- P08909
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51916.005 Da
References
- Haria M, Fitton A, McTavish D: Trazodone. A review of its pharmacology, therapeutic use in depression and therapeutic potential in other disorders. Drugs Aging. 1994 Apr;4(4):331-55. doi: 10.2165/00002512-199404040-00006. [Article]
- Li AA, Marek GJ, Hand TH, Seiden LS: Antidepressant-like effects of trazodone on a behavioral screen are mediated by trazodone, not the metabolite m-chlorophenylpiperazine. Eur J Pharmacol. 1990 Feb 27;177(3):137-44. doi: 10.1016/0014-2999(90)90263-6. [Article]
- Jenck F, Moreau JL, Mutel V, Martin JR: Brain 5-HT1C receptors and antidepressants. Prog Neuropsychopharmacol Biol Psychiatry. 1994 May;18(3):563-74. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [Article]
- Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [Article]
- Flockhart Table of Drug Interactions [Link]
- Trazodone [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Wen B, Ma L, Rodrigues AD, Zhu M: Detection of novel reactive metabolites of trazodone: evidence for CYP2D6-mediated bioactivation of m-chlorophenylpiperazine. Drug Metab Dispos. 2008 May;36(5):841-50. doi: 10.1124/dmd.107.019471. Epub 2008 Jan 31. [Article]
- Najibi A, Heidari R, Zarifi J, Jamshidzadeh A, Firoozabadi N, Niknahad H: Evaluating the Role of Drug Metabolism and Reactive Intermediates in Trazodone-Induced Cytotoxicity toward Freshly-Isolated Rat Hepatocytes. Drug Res (Stuttg). 2016 Nov;66(11):592-596. doi: 10.1055/s-0042-109536. Epub 2016 Sep 19. [Article]
- Mrazek DA: Psychiatric pharmacogenomic testing in clinical practice. Dialogues Clin Neurosci. 2010;12(1):69-76. [Article]
- Wu AH, Lorizio W, Tchu S, Lynch K, Gerona R, Ji W, Ruan W, Ruddy KJ, Desantis SD, Burstein HJ, Ziv E: Estimation of tamoxifen metabolite concentrations in the blood of breast cancer patients through CYP2D6 genotype activity score. Breast Cancer Res Treat. 2012 Jun;133(2):677-83. doi: 10.1007/s10549-012-1963-2. [Article]
- Chubak J, Bowles EJ, Yu O, Buist DS, Fujii M, Boudreau DM: Breast cancer recurrence in relation to antidepressant use. Cancer Causes Control. 2016 Jan;27(1):125-36. doi: 10.1007/s10552-015-0689-y. Epub 2015 Oct 30. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Stormer E, von Moltke LL, Perloff MD, Greenblatt DJ: P-glycoprotein interactions of nefazodone and trazodone in cell culture. J Clin Pharmacol. 2001 Jul;41(7):708-14. [Article]
- Smolders EJ, de Kanter CT, de Knegt RJ, van der Valk M, Drenth JP, Burger DM: Drug-Drug Interactions Between Direct-Acting Antivirals and Psychoactive Medications. Clin Pharmacokinet. 2016 Dec;55(12):1471-1494. doi: 10.1007/s40262-016-0407-2. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55