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PubChem
Name: Trazodone
PubChem Compound ID: 5533
Description: A serotonin uptake inhibitor that is used as an antidepressive agent. 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. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)
Molecular formula: C19H22ClN5O
Molecular weight: 371.864 g/mol
Synonyms:
NINDS_000196; 19794-93-5; Desirel; Beneficat; Trazodone; 1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-; S-Triazolo[4, 3-a]pyridin-3(2H)-one, 2-[3-[4-(m-chlorophenyl)-1-piperazinyl]propyl]-, monohydrochloride; 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-; Trazodon; KBio1_000196.
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DrugBank
Identification
Name: Trazodone
Name (isomeric): DB00656
Drug Type: small molecule
Description: A serotonin uptake inhibitor that is used as an antidepressive agent. 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. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)
Synonyms:
Trazodone Hcl; Trazodonum [INN-Latin]; Trazodona [INN-Spanish]; Trazodone Hydrochloride
Brand: Bimaran, Trazodon, Desirel, Trazolan, Trazonil, Pragmazone, Desyrel Dividose, Trittico, Trazalon, Beneficat, Trialodine, Molipaxin, Thombran, Desyrel, Sideril, Tombran, Trazodil
Category: Anti-anxiety Agents, Antidepressants, Second-Generation, Antidepressive Agents, Second-Generation, Serotonin Uptake Inhibitors
CAS number: 19794-93-5
Pharmacology
Indication: For the treatment of depression.
Pharmacology:
Trazodone is an antidepressant and hypnotic chemically unrelated to tricyclic, tetracyclic, or other known antidepressant agents. The mechanism of trazodone's antidepressant action in man is not fully understood. In animals, trazodone selectively inhibits serotonin uptake by brain synaptosomes and potentiates the behavioral changes induced by the s...
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Mechanism of Action:
Trazodone binds at 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 neuro...
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Absorption: Rapidly and almost completely absorbed following oral administration. Food may decrease the rate and extent of absorption.
Protein binding: 89-95% bound to plasma proteins in vitro
Biotransformation: Undergoes extensive hepatic metabolism via hydroxylation, N-dealkylation, N-oxidation and splitting of the pyridine ring. Cytochrome P450 (CYP) 3A4 catalyzes the formation of the major active metabolite, m-chlorophenylpiperazine (m-CPP). Metabolites may be further conjugated to glucuonic acid or glutathione. CYP2D6 is responsible for 4'-hydroxylation of m-CPP and the formation of at least one glutathione conjugates of m-CPP, a quinone imine-sulhydryl adduct. Oxotriazolopyridinpropionic acid, an inactive metabolite, and its conjugates account for about 20% of the total excreted oral dose. Less than 1% of the oral dose is excreted unchanged. Approximately 70-75% of the dose is eliminated in urine with the remainder being excreted in feces via biliary elimination.
Half Life: Undergoes biphasic elimination with an initial phase t1/2 α of 3-6 hours and a terminal phase t1/2 β of 5-9 hours.
Toxicity: LD50=96mg/kg (i.v. in mice)
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Food decreases the rate and extent of absorption.
Avoid alcohol.
Drug interaction:
Ginkgo bilobaIncreased effect and toxicity of both agents
MeperidineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
SertralineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TrimipramineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
LithiumIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
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