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N5536

Sigma-Aldrich

Nefazodone hydrochloride

≥98% (HPLC), solid, selective serotonin reuptake inhibitor

Synonym(s):

2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride, BMY-13754, MJ-13754-1, Serzone

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About This Item

Empirical Formula (Hill Notation):
C25H32ClN5O2 · HCl
CAS Number:
Molecular Weight:
506.47
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Product Name

Nefazodone hydrochloride, ≥98% (HPLC), solid

Quality Level

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

DMSO: ≥10 mg/mL
H2O: insoluble

originator

Bristol-Myers Squibb

SMILES string

O=C1N(CCCN2CCN(C3=CC=CC(Cl)=C3)CC2)N=C(CC)N1CCOC4=CC=CC=C4.Cl

InChI

1S/C25H32ClN5O2.ClH/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22;/h3-6,8-11,20H,2,7,12-19H2,1H3;1H

InChI key

DYCKFEBIOUQECE-UHFFFAOYSA-N

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Biochem/physiol Actions

Novel antidepressant; mixed 5-HT2A serotonin receptor antagonist/serotonin uptake inhibitor.

Features and Benefits

This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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James A Dykens et al.
Toxicological sciences : an official journal of the Society of Toxicology, 103(2), 335-345 (2008-03-18)
Mitochondrial toxicity is increasingly implicated in a host of drug-induced organ toxicities, including hepatotoxicity. Nefazodone was withdrawn from the U.S. market in 2004 due to hepatotoxicity. Accordingly, we evaluated nefazodone, another triazolopyridine trazodone, plus the azaspirodecanedione buspirone, for cytotoxicity and
R Davis et al.
Drugs, 53(4), 608-636 (1997-04-01)
Nefazodone hydrochloride is a phenylpiperazine antidepressant with a mechanism of action that is distinct from those of other currently available drugs. It potently and selectively blocks postsynaptic serotonin (5-hydroxytryptamine; 5-HT) 5-HT2A receptors and moderately inhibits serotonin and noradrenaline (norepinephrine) reuptake.
Nader Perroud et al.
Pharmacogenomics, 12(3), 365-377 (2011-04-01)
This study investigated clinical and genetic predictors of increasing suicidal ideation during antidepressant treatment. A total of 131 depressed outpatients were allocated to four antidepressants (paroxetine, venlafaxine, clomipramine or nefazodone) in a sequential step procedure until remission. Suicidality was assessed
Michael J Constantino et al.
Journal of consulting and clinical psychology, 80(3), 354-364 (2012-05-02)
Interpersonal theories posit that chronically depressed individuals have hostile and submissive styles in their social interactions, which may undermine their interpersonal effectiveness and maintain their depression. Recent findings support this theory and also show that patients' interpersonal impact messages, as
Spilios V Argyropoulos et al.
Journal of sleep research, 18(3), 342-348 (2009-06-25)
It has been suggested that increase in delta sleep ratio (DSR), a marker for the relative distribution of slow wave activity (SWA) over night time, is associated with clinical response to antidepressant treatment. We examined this index and its relationship

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