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N5536

Nefazodone hydrochloride

Name: Nefazodone hydrochloride
Brand: SIGMA

≥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:

82752-99-6

Molecular Weight:

506.47

UNSPSC Code:

12352200

PubChem Substance ID:

24724551

NACRES:

NA.77

MDL number:

MFCD00935760

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

desiccated

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Properties

Product Name

Nefazodone hydrochloride, ≥98% (HPLC), solid

Quality Level

100

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

Gene Information

human ... HTR2A(3356), HTR2C(3358), SLC6A2(6530), SLC6A4(6532)

Description

Biochem/physiol Actions

Novel antidepressant; mixed 5-HT_2A 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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Long-term exposure of mouse pancreatic islets to oleate or palmitate results in reduced glucose-induced somatostatin and oversecretion of glucagon.

S C Collins et al.

Diabetologia, 51(9), 1689-1693 (2008-07-16)

Long-term exposure to NEFAs leads to inhibition of glucose-induced insulin secretion. We tested whether the release of somatostatin and glucagon, the two other major islet hormones, is also affected. Mouse pancreatic islets were cultured for 72 h at 4.5 or

Comparison of the bioactivation potential of the antidepressant and hepatotoxin nefazodone with aripiprazole, a structural analog and marketed drug.

Jonathan N Bauman et al.

Drug metabolism and disposition: the biological fate of chemicals, 36(6), 1016-1029 (2008-03-12)

In vitro metabolism/bioactivation of structurally related central nervous system agents nefazodone (hepatotoxin) and aripiprazole (nonhepatotoxin) were undertaken in human liver microsomes in an attempt to understand the differences in toxicological profile. NADPH-supplemented microsomal incubations of nefazodone and glutathione generated conjugates

In vitro assessment of mitochondrial dysfunction and cytotoxicity of nefazodone, trazodone, and buspirone.

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

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