CHEBI:9654 - trazodone

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ChEBI Name trazodone
ChEBI ID CHEBI:9654
Definition An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H22ClN5O
Net Charge 0
Average Mass 371.86400
Monoisotopic Mass 371.151
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
SMILES Clc1cccc(c1)N1CCN(CCCn2nc3ccccn3c2=O)CC1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trazodone (CHEBI:9654) has role adrenergic antagonist (CHEBI:37887)
trazodone (CHEBI:9654) has role antidepressant (CHEBI:35469)
trazodone (CHEBI:9654) has role anxiolytic drug (CHEBI:35474)
trazodone (CHEBI:9654) has role H1-receptor antagonist (CHEBI:37955)
trazodone (CHEBI:9654) has role sedative (CHEBI:35717)
trazodone (CHEBI:9654) has role serotonin uptake inhibitor (CHEBI:50949)
trazodone (CHEBI:9654) is a N-alkylpiperazine (CHEBI:46845)
trazodone (CHEBI:9654) is a N-arylpiperazine (CHEBI:46848)
trazodone (CHEBI:9654) is a monochlorobenzenes (CHEBI:83403)
trazodone (CHEBI:9654) is a triazolopyridine (CHEBI:46746)
Incoming trazodone hydrochloride (CHEBI:9655) has part trazodone (CHEBI:9654)
IUPAC Name
2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
INNs Sources
trazodona ChEBI
trazodone ChEBI
trazodonum ChEBI
Synonyms Sources
2-(3-[4-(3-chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one NIST Chemistry WebBook
Trazodone KEGG COMPOUND
Manual Xrefs Databases
2717 DrugCentral
C07156 KEGG COMPOUND
D08626 KEGG DRUG
DB00656 DrugBank
LSM-3580 LINCS
Trazodone Wikipedia
US3381009 Patent
View more database links
Registry Numbers Types Sources
19794-93-5 CAS Registry Number ChemIDplus
19794-93-5 CAS Registry Number NIST Chemistry WebBook
628010 Beilstein Registry Number Beilstein
Last Modified
22 February 2017
General Comment
2011-01-11 Trazodone is a serotonin uptake inhibitor that is used as the hydrochloride salt as an antidepressive agent. It does not have very significant antimuscarinic properties, but has a marked sedative action. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety.