Name: | Trazodone |
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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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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; Spectrum4_000755; Spectrum_001424; Desyrel(trazodone hcl salt); KBio2_004472; Lopac-T-6154; KBio2_007040; Prestwick0_000292; S-Trizolo[4,3-a]pyridin-3(2H)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-, hydrochloride; Spectrum3_001560; 1,2,4-Triazolo[4,3-a]pyridin-3 (2H)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-, monohydrochloride; Bimaran; Sideril; CAS-25332-39-2; Trazonil; BRN 0628010; 25332-39-2; Spectrum2_000854; KBio2_001904; EINECS 243-317-1; KBioSS_001904; Trazodil; s-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-; SPBio_000867; C07156; SPBio_002443; NSC292811; DivK1c_000196; Prestwick1_000292; Trazodona [Spanish]; Trazodone hydrochloride; Molipaxin; NCGC00016035-01; NCGC00016035-02; KBioGR_001110; Trazodonum [INN-Latin]; KBio3_002540; Trazalon; Trazodona [INN-Spanish]; 2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]-s-triazolo[4, 3-a]pyridin-3(2H)-one monohydrochloride; AF-1161; Desyrel; Trazodonum [Latin]
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Name: | Trazodone |
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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
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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 |
Indication: | For the treatment of depression. |
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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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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 serotonin precursor, 5-hydroxytryptophan. Cardiac conduction effects of trazodone in the anesthetized dog are qualitatively dissimilar and quantitatively less pronounced than those seen with tricyclic antidepressants. Trazodone is not a monoamine oxidase inhibitor and, unlike amphetamine-type drugs, does not stimulate the central nervous system. In man, trazodone is well absorbed after oral administration without selective localization in any tissue. Since the clearance of trazodone from the body is sufficiently variable, in some patients trazodone may accumulate in the plasma.
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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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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 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 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.
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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 |
Food interaction: |
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Drug interaction: |
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UniProt ID: | P28223 | ||||||
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Gene: | HTR2A | ||||||
Actions: | antagonist | ||||||
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UniProt ID: | P28335 | ||
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Gene: | HTR2C | ||
Actions: | agonist | ||
References: |
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UniProt ID: | P31645 | |
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Gene: | SLC6A4 | |
Actions: | inhibitor | |
References: |
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UniProt ID: | P08908 | |||
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Gene: | HTR1A | |||
Actions: | partial agonist | |||
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UniProt ID: | P35367 | |||
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Gene: | HRH1 | |||
Actions: | antagonist | |||
References: |
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UniProt ID: | P35348 | |
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Gene: | ADRA1A | |
Actions: | antagonist | |
References: |
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UniProt ID: | P08913 | |||
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Gene: | ADRA2A | |||
Actions: | antagonist | |||
References: |
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UniProt ID: | P08684 | ||||
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Gene: | CYP3A4 | ||||
Actions: | substrate | ||||
References: |
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UniProt ID: | P20815 | |
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Gene: | CYP3A5 | |
Actions: | substrate | |
References: |
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UniProt ID: | P24462 | |
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Gene: | CYP3A7 | |
Actions: | substrate | |
References: |
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UniProt ID: | P10635 | ||
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Gene: | CYP2D6 | ||
Actions: | substrate | ||
References: |
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UniProt ID: | P08183 | |
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Gene: | ABCB1 | |
Actions: | inducer | |
References: |
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UniProt ID: | P02763 | |
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Gene: | ORM1 | |
References: |
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