Completing data — usually done within a minute
Basic information
- CAS
82752-99-6- Standard SMILES
CCc1nn(CCCN2CCN(c3cccc(Cl)c3)CC2)c(=O)n1CCOc1ccccc1.Cl- InChIKey
DYCKFEBIOUQECE-UHFFFAOYSA-N- Molecular formula
- C25H33Cl2N5O2
- Average molar mass
- 506.5 g/mol
- Monoisotopic mass
- 505.20113066
Overview
Nefazodone hydrochloride is a hydrochloride. It contains a nefazodone.
Names & identifiers
- Preferred name
- Nefazodone Hydrochloride
- IUPAC
- 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-5-ethyl-4-(2-phenoxyethyl)-1,2,4-triazol-3-one;hydrochloride
Names & synonyms
NEFAZODONE HYDROCHLORIDE82752-99-6Nefazodone HclDutoninSerzoneBMY 13754MJ 13,754-1DTXSID8046088MJ-13754-1BMY-1375427X63J94GRNSC-760344
Show more names
CHEBI:7495DTXCID60260882-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-5-ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochlorideNefazadone HCl2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-5-ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochlorideRefChem:57774MenfazonaReseril
Database identifiers
- CAS
82752-99-6- PubChem CID
- 54911
- DTXSID
DTXSID8046088- ChEMBL
CHEMBL1200492- ChEBI
CHEBI:7495- UNII
- 27X63J94GR
- EC Number
- 875-483-1
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 51.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 649
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationNefazodone hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Treatment
Treatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to the wide distribution of nefazodone in body tissues, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. No specific antidotes for nefazodone are known. (L1712)
Health EffectsSerious side effects include an allergic reaction, fainting, or painful/prolonged erection. [Wikipedia]
Exposure RoutesNefazodone is rapidly and completely absorbed. Its absolute bioavailability is low (about 20%).
Toxicity Summary
Within the serotonergic system, nefazodone acts as an antagonist at type 2 serotonin (5-HT<sub>2</sub>) post-synaptic receptors and, like fluoxetine-type antidepressants, inhibits pre-synaptic serotonin (5-HT) reuptake. These mechanisms increase the amount of serotonin available to interact with 5-HT receptors. Within the noradrenergic system, nefazodone inhibits norepinephrine uptake minimally. Nefazodone also antagonizes alpha(1)-adrenergic receptors, producing sedation, muscle relaxation, and a variety of cardiovascular effects. Nefazodone's affinity for benzodiazepine, cholinergic, dopaminergic, histaminic, and beta or alpha(2)-adrenergic receptors is not significant.
Signs and SymptomsCases of life-threatening hepatic failure have been reported in patients treated with nefazodone.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Nefazodone hydrochloride
vMost-DILI-concern
8
Box warning
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Hepatic. Route of Elimination: Nefazodone is extensively metabolized after oral administration by n-dealkylation and aliphatic and aromatic hydroxylation, and less than 1% of administered nefazodone is excreted unchanged in urine. Half Life: 2-4 hours
FDA Pharmacological Classification
NEFAZODONE HYDROCHLORIDE
Serotonin Reuptake Inhibitor [EPC]
MeSH Pharmacological Classification
Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS.
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.
Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.
Uses & manufacturing
UsesNefazodone (sold as Serzone, Nefadar) is a psychoactive drug and antidepressant. [wikipedia]
Related reactions
4 records
Compound notes
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