Trazodone Hydrochloride
Basic information
- CAS
19666-36-5- Standard SMILES
Cl.O=c1n(CCCN2CCN(c3cccc(Cl)c3)CC2)nc2ccccn12- InChIKey
OHHDIOKRWWOXMT-UHFFFAOYSA-N- Molecular formula
- C19H23Cl2N5O
- Average molar mass
- 408.3 g/mol
- Monoisotopic mass
- 407.1279658
Overview
Trazodone hydrochloride is a hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride. It has a role as an antidepressant, a sedative, an adrenergic antagonist, a H1-receptor antagonist and a serotonin uptake inhibitor. It contains a trazodone.
Names & identifiers
- Preferred name
- Trazodone Hydrochloride
- IUPAC
- 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;hydrochloride
- English name
- 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride
- Molecular formula
- C19H23Cl2N5O
- Molecular weight
- 408.32482
Names & synonyms
Trazodone hydrochloride25332-39-2Trazodone HclTrialodineOleptroAF-1161DTXSID80446266E8ZO8LRNMNSC-292811RALDESY2-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2H)-one monohydrochlorideCHEBI:9655
Show more names
Einecs 243-216-22-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride
1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-, monohydrochlorideDTXCID6024626NSC2928112-(3-(4-(3-Chlorophenyl)piperazin-1-y)propyl)-1,2,4-triazolo(4,3-a)pyridine-3(2H)-one hydrochlorideTrazamineMolipaxin cr2-[3-[4-(m-Chlorophenyl)-1-piperazinyl]propyl]-s-triazolo[4,3-a]pyridin-3(2H)-one monohydrochlorideTrazodone Hydrochoride
Database identifiers
- CAS
19666-36-5、25332-39-2- PubChem CID
- 62935
- DTXSID
DTXSID8044626- ChEMBL
Properties
Computed structural properties
- Topological polar surface area
- 42.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 611
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section189.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 57 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Treatment
There is no specific antidote for Trazodone. Treatment should be symptomatic and supportive in the case of hypotension or excessive sedation. Any patient suspected of having taken an overdose should have the stomach emptied by gastric lavage. Forced diuresis may be useful in facilitating elimination of the drug. (L1712)
Exposure RoutesRapidly and almost completely absorbed following oral administration. Food may decrease the rate and extent of absorption.
Toxicity Summary
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.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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 t<sub>1/2 α</sub> of 3-6 hours and a terminal phase t<sub>1/2 β</sub> of 5-9 hours.
FDA Pharmacological Classification
TRAZODONE HCL
Serotonin Reuptake Inhibitor [EPC]
TRAZODONE HYDROCHLORIDE
Serotonin Reuptake Inhibitor [EPC]
TRAZODONE HYDROCHLORIDE ORAL
Serotonin Reuptake Inhibitor [EPC]
MeSH Pharmacological Classification
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.
Compounds that specifically inhibit the reuptake of serotonin in the brain.
Uses & manufacturing
UsesFor the treatment of depression.
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Compound notes
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