Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H22ClN5O.ClH |
| Molecular Weight | 408.325 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.ClC1=CC(=CC=C1)N2CCN(CCCN3N=C4C=CC=CN4C3=O)CC2
InChI
InChIKey=OHHDIOKRWWOXMT-UHFFFAOYSA-N
InChI=1S/C19H22ClN5O.ClH/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;1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H22ClN5O |
| Molecular Weight | 371.864 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00656 | https://www.drugs.com/trazodone.html | http://reference.medscape.com/drug/oleptro-trazodone-d-342965
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00656 | https://www.drugs.com/trazodone.html | http://reference.medscape.com/drug/oleptro-trazodone-d-342965
Trazodone (brand name Oleptro, Desyrel, etc) is a serotonin uptake inhibitor that is used as an antidepressive agent. Trazodone binds to the 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at the H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS. Because of its lack of anticholinergic side effects, trazodone is especially useful in situations in which antimuscarinic effects are particularly problematic (e.g., in patients with benign prostatic hyperplasia, closed-angle glaucoma, or severe constipation). Trazodone's propensity to cause sedation is a dual-edged sword. For many patients, the relief from agitation, anxiety, and insomnia can be rapid; for other patients, including those individuals with considerable psychomotor retardation and feelings of low energy, therapeutic doses of trazodone may not be tolerable because of sedation. Trazodone elicits orthostatic hypotension in some patients, probably as a consequence of α1-adrenergic receptor blockade. Mania has been observed in association with trazodone treatment, including in patients with bipolar disorder, as well as in patients with previous diagnoses of major depression. Compared to the reversible MAOI antidepressant drug moclobemide, significantly more impairment of vigilance occurs with trazodone.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9986703 |
17.0 nM [IC50] | ||
Target ID: CHEMBL2096904 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9986703 |
|||
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568799 |
223.87 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | DESYREL Approved UseTrazodone Hydrochloride Tablets USP are indicated for the treatment of major depressive disorder (MDD) in adults. The efficacy of Trazodone Hydrochloride Tablets USP has been established in trials with the immediate release formulation of trazodone [see Clinical Studies (14) Launch Date1981 |
|||
| Primary | DESYREL Approved UseTrazodone Hydrochloride Tablets USP are indicated for the treatment of major depressive disorder (MDD) in adults. The efficacy of Trazodone Hydrochloride Tablets USP has been established in trials with the immediate release formulation of trazodone [see Clinical Studies (14) Launch Date1981 |
|||
| Primary | DESYREL Approved UseTrazodone Hydrochloride Tablets USP are indicated for the treatment of major depressive disorder (MDD) in adults. The efficacy of Trazodone Hydrochloride Tablets USP has been established in trials with the immediate release formulation of trazodone [see Clinical Studies (14) Launch Date1981 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.88 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1438031/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAZODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1438031/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAZODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1438031/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAZODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5% |
unknown, oral |
TRAZODONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2000 mg single, oral Overdose |
unknown, 22 years |
Disc. AE: Drowsiness, Hypertension... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: Hypertension (1 patient) Vomiting (1 patient) |
2900 mg single, oral Overdose |
unknown, 25 years |
Disc. AE: Dry mouth, Upset stomach... AEs leading to discontinuation/dose reduction: Dry mouth (1 patient) Sources: Upset stomach (1 patient) Drowsiness (1 patient) |
6450 mg single, oral Overdose Dose: 6450 mg Route: oral Route: single Dose: 6450 mg Sources: |
unknown, 37 years |
Disc. AE: Seizures, Hyponatremia... AEs leading to discontinuation/dose reduction: Seizures (grade 5, 1 patient) Sources: Hyponatremia (grade 5, 1 patient) |
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: |
unknown, 55 years |
Disc. AE: Arrhythmia... AEs leading to discontinuation/dose reduction: Arrhythmia (1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Drowsiness | 1 patient Disc. AE |
2000 mg single, oral Overdose |
unknown, 22 years |
| Hypertension | 1 patient Disc. AE |
2000 mg single, oral Overdose |
unknown, 22 years |
| Vomiting | 1 patient Disc. AE |
2000 mg single, oral Overdose |
unknown, 22 years |
| Drowsiness | 1 patient Disc. AE |
2900 mg single, oral Overdose |
unknown, 25 years |
| Dry mouth | 1 patient Disc. AE |
2900 mg single, oral Overdose |
unknown, 25 years |
| Upset stomach | 1 patient Disc. AE |
2900 mg single, oral Overdose |
unknown, 25 years |
| Hyponatremia | grade 5, 1 patient Disc. AE |
6450 mg single, oral Overdose Dose: 6450 mg Route: oral Route: single Dose: 6450 mg Sources: |
unknown, 37 years |
| Seizures | grade 5, 1 patient Disc. AE |
6450 mg single, oral Overdose Dose: 6450 mg Route: oral Route: single Dose: 6450 mg Sources: |
unknown, 37 years |
| Arrhythmia | 1 patient Disc. AE |
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: |
unknown, 55 years |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [IC50 23 uM] | ||||
| yes [IC50 43 uM] | ||||
| yes [IC50 45 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11452702/ |
yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes | yes (co-administration study) Comment: [PMID:7482685]: CYP2D6-mediated metabolism of trazodone is inhibited by coadministration of thioridazine, which is an inhibitor of this isozyme. |
|||
| yes | yes (co-administration study) Comment: [DESYREL® LABEL]: The concomitant use of DESYREL and strong CYP3A4 inhibitors increased the exposure of trazodone compared to the use of DESYREL alone. The concomitant use of DESYREL and strong CYP3A4 inducers decreased the exposure of trazodone compared to the use of DESYREL alone. |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| New colorimetric methods for the determination of trazodone HCl, famotidine, and diltiazem HCl in their pharmaceutical dosage forms. | 2003-07 |
|
| A fatal drug interaction between oxycodone and clonazepam. | 2003-05 |
|
| Olanzapine in the treatment-resistant, combat-related PTSD--a series of case reports. | 2003-05 |
|
| Short-term exposure to low-dose ritonavir impairs clearance and enhances adverse effects of trazodone. | 2003-04 |
|
| Unexplained transient hyperphosphatemia is more common in acute psychiatric disorders than in acute medical-surgical conditions. | 2003-03-25 |
|
| [Depression in epilepsy: symptom or syndrome?]. | 2003-03-21 |
|
| Electroanalytical characteristics of piribedil and its differential pulse and square wave voltammetric determination in pharmaceuticals and human serum. | 2003-03-10 |
|
| Mianserin and trazodone significantly attenuate the intensity of opioid withdrawal symptoms in mice. | 2003-03 |
|
| A multicentre prospective controlled study to determine the safety of trazodone and nefazodone use during pregnancy. | 2003-03 |
|
| Assessment of the contributions of CYP3A4 and CYP3A5 in the metabolism of the antipsychotic agent haloperidol to its potentially neurotoxic pyridinium metabolite and effect of antidepressants on the bioactivation pathway. | 2003-03 |
|
| Pharmacologic management by clinical pharmacists of behavioral and psychological symptoms of dementia in nursing home residents: results from a pilot study. | 2003-02 |
|
| Association of low dose trazodone treatment with aggravated angle-closure glaucoma. | 2003-02 |
|
| Dissociative symptoms from combined treatment with sertraline and trazodone. | 2003 |
|
| Treatment of sleep disturbance in alcohol recovery: a national survey of addiction medicine physicians. | 2003 |
|
| Simultaneous quantification of citalopram, clozapine, fluoxetine, norfluoxetine, maprotiline, desmethylmaprotiline and trazodone in human serum by HPLC analysis. | 2002-12 |
|
| The treatment of generalised anxiety disorder. A systematic review. | 2002-12 |
|
| In vitro identification of metabolic pathways and cytochrome P450 enzymes involved in the metabolism of etoperidone. | 2002-11 |
|
| Clitoral priapism: a rare condition presenting as a cause of vulvar pain. | 2002-11 |
|
| Voluntary undertaking rule and duty to warn. | 2002-10-01 |
|
| Voltammetric analysis of trazodone HCl in pharmaceuticals and biological fluids. | 2002-09-05 |
|
| Sleep in posttraumatic stress disorder. | 2002-09 |
|
| The pharmacologic management of SSRI-induced side effects: a survey of psychiatrists. | 2002-09 |
|
| Erectile dysfunction: oral pharmacotherapy options. | 2002-09 |
|
| Alterations in 5-HT(1A) receptors and adenylyl cyclase response by trazodone in regions of rat brain. | 2002-08-16 |
|
| Alpha(1)-adrenoceptor antagonists. 4. Pharmacophore-based design, synthesis, and biological evaluation of new imidazo-, benzimidazo-, and indoloarylpiperazine derivatives. | 2002-08-15 |
|
| Effects of trazodone and imipramine on the biological rhythm: an analysis of sleep EEG and body core temperature. | 2002-08 |
|
| Relationship between plasma concentrations of trazodone and its active metabolite, m-chlorophenylpiperazine, and its clinical effect in depressed patients. | 2002-08 |
|
| Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol. | 2002-08 |
|
| Priapism associated with trazodone in an adolescent with autism. | 2002-07 |
|
| Masturbatory guilt leading to severe depression and erectile dysfunction. | 2002-06-27 |
|
| An overview of the clinical efficacy of mirtazapine. | 2002-06 |
|
| Pharmacological aspects of erectile dysfunction. | 2002-06 |
|
| [Chronobiological research on antidepressant drugs: the effect of the antidepressant drugs, trazodone and imipramine on the circadian rhythm using electroencephalography in healthy volunteers]. | 2002-06 |
|
| [Latest therapies for treating dementia]. | 2002-05-15 |
|
| Paroxetine associated hepatotoxicity: a report of 3 cases and a review of the literature. | 2002-05 |
|
| [Progress in therapy of erectile dysfunction. New orally administered drugs]. | 2002-05 |
|
| Psychotropic drugs and the ECG: focus on the QTc interval. | 2002-05 |
|
| Detecting drug-drug interactions in medication profiles of psychiatric inpatients: a two-stage approach. | 2002-04 |
|
| Citalopram-induced priapism. | 2002-04 |
|
| Serotonin releasing agents. Neurochemical, therapeutic and adverse effects. | 2002-04 |
|
| Induction of hyperlocomotion in mice exposed to a novel environment by inhibition of serotonin reuptake. A pharmacological characterization of diverse classes of antidepressant agents. | 2002-04 |
|
| A hemodialysis patient with trazodone-induced parkinsonism. | 2002-02 |
|
| Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. | 2002-02 |
|
| Potential interactions between herbal medicines and conventional drug therapies used by older adults attending a memory clinic. | 2002 |
|
| No long-term effect of behavioral treatment on psychotropic drug use for agitation in Alzheimer's disease patients. | 2002 |
|
| Effects of psychotropic drugs on seizure threshold. | 2002 |
|
| Central nervous system agents in the treatment of erectile dysfunction: how do they work? | 2001-12 |
|
| A display of hypomania in a depressed male in response to fluvoxamine. | 2001-10 |
|
| Does behavioral improvement with haloperidol or trazodone treatment depend on psychosis or mood symptoms in patients with dementia? | 2001-10 |
|
| Successful treatment with trazodone for repetitive behavior in schizophrenia. | 2001 |
Sample Use Guides
Starting dose: 150 mg once daily. May be increased by 75 mg per day
every three days. Maximum dose: 375 mg per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9986703
The receptors affinity was estimated at Nova Screen Laboratories by the ability of the Trazodone to displace selective radioligands. The assays were carried out using the following: for 5HT2A – rat cortical membranes, [3H]ketanserin (1.0 nM) as radioligand and methysergide as reference compound; for alpha1 - rat cortical membranes, [3H]prazosin (0.5 nM) and prazosin; for 5HT-R - rat forebrain membranes, [3H]citalopram (0.7 nM) and imipramine. In the preliminary binding assay, the results are expressed as inhibition percentage compared to results without drug and represent the average of duplicate tubes at each tested concentration in a single experiment.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:54:13 GMT 2025
by
admin
on
Mon Mar 31 17:54:13 GMT 2025
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| Record UNII |
6E8ZO8LRNM
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C265
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25332-39-2
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9655
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C47767
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82112
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DTXSID8044626
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DBSALT000344
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62935
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100000090309
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292811
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6E8ZO8LRNM
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CHEMBL621
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6E8ZO8LRNM
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m11010
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246-855-5
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SUB15596MIG
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1673500
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25332-39-2
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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IMPURITY -> PARENT |
UNSPECIFIED
|
||
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IMPURITY -> PARENT |
UNSPECIFIED
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
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IMPURITY -> PARENT |
UNSPECIFIED
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
|
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IMPURITY -> PARENT |
UNSPECIFIED
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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