Nefazodone hydrochloride - CAS 82752-99-6
Catalog number:
82752-99-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C25H33Cl2N5O2
Molecular Weight:
506.46
COA:
Inquire
Targets:
5-HT Receptor
Description:
Nefazodone hydrochloride is a selective serotonin 5-HT2 receptor antagonist. It is used as an antidepressant that shows no cardiac toxicity or anticholinergic activity common with tricyclic antidepressants. It is a phenylpiperazin derivative, whose structure is similar to that of some known antidepressants. It was developed by Bristol-Myers Squibb.
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Purity:
95%
Appearance:
White solid
Synonyms:
3H-1,2,4-Triazol-3-one, 2-3-4-(3-chlorophenyl)-1-piperazinylpropyl-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-, monohydrochloride;Nefazodone HCl;BMY-13754;MJ-13754-1;2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride;2,4-Dihydro-2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride;Serzone;Dutonin;Menfazona
Solubility:
DMSO:17mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Nefazodone hydrochloride is used as an antidepressant that shows no cardiac toxicity or anticholinergic activity common with tricyclic antidepressants.
Quality Standard:
USP standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
599.6ºC at 760 mmHg
Melting Point:
186-188 °C | Condition: Solv: isopropanol (67-63-0)
InChIKey:
DYCKFEBIOUQECE-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
CCC1=NN(C(=O)N1CCOC2=CC=CC=C2)CCCN3CCN(CC3)C4=CC(=CC=C4)Cl.Cl
Current Developer:
Nefazodone hydrochloride was developed by Bristol-Myers Squibb.
1.Repurposing Registered Drugs as Antagonists for Protease-Activated Receptor 2.
Xu W1, Lim J1, Goh CY1, Suen JY1, Jiang Y1, Yau MK1, Wu KC1, Liu L1, Fairlie DP1. J Chem Inf Model. 2015 Oct 26;55(10):2079-84. doi: 10.1021/acs.jcim.5b00500. Epub 2015 Oct 12.
Virtual screening of a drug database identified Carvedilol, Loratadine, Nefazodone and Astemizole as PAR2 antagonists, after ligand docking and molecular dynamics simulations using a PAR2 homology model and a putative binding mode of a known PAR2 ligand. The drugs demonstrated competitive binding and antagonism of calcium mobilization and ERK1/2 phosphorylation in CHO-hPAR2 transfected cells, while inhibiting IL-6 secretion in PAR2 expressing MDA-MB-231 breast cancer cells. This research highlights opportunities for GPCR hit-finding from FDA-approved drugs.
2.Reactive Metabolites: Current and Emerging Risk and Hazard Assessments.
Thompson RA1, Isin EM2, Ogese MO3, Mettetal JT4, Williams DP3. Chem Res Toxicol. 2016 Apr 18;29(4):505-33. doi: 10.1021/acs.chemrestox.5b00410. Epub 2016 Jan 6.
Although idiosyncratic adverse drug reactions are rare, they are still a major concern to patient safety. Reactive metabolites are widely accepted as playing a pivotal role in the pathogenesis of idiosyncratic adverse drug reactions. While there are today well established strategies for the risk assessment of stable metabolites within the pharmaceutical industry, there is still no consensus on reactive metabolite risk assessment strategies. This is due to the complexity of the mechanisms of these toxicities as well as the difficulty in identifying and quantifying short-lived reactive intermediates such as reactive metabolites. In this review, reactive metabolite risk and hazard assessment approaches are discussed, and their pros and cons highlighted. We also discuss the nature of idiosyncratic adverse drug reactions, using acetaminophen and nefazodone to exemplify the complexity of the underlying mechanisms of reactive metabolite mediated hepatotoxicity.
3.Antidepressants and Driving in Older Adults: A Systematic Review.
Cameron DH1, Rapoport MJ1. Can J Aging. 2016 Apr 19:1-8. [Epub ahead of print]
With an increasing number of older drivers who are prescribed antidepressants, the potential consequences of antidepressant use on driving skills in an aging population are becoming a pressing issue. We conducted a systematic review using MEDLINE, targeting articles specifically pertaining to antidepressants and driving in a population or subgroup of older adults (≥ 55 years of age). The search yielded 267 references, nine of which pertained to the effects of antidepressants on driving in older adults. The single experimental study found imipramine to have detrimental effects on highway driving, whereas nefazodone did not. Seven of eight population-based studies reported a significant increased risk of involvement in a collision associated with antidepressant use. Although the studies indicated a negative effect of antidepressants on driving, the epidemiological designs cannot exclude the possibility that the underlying illness, generally major depression, is the culprit.
4.Drug-induced liver injury associated with antidepressive psychopharmacotherapy: An explorative assessment based on quantitative signal detection using different MedDRA terms.
Gahr M1, Zeiss R1, Lang D2, Connemann BJ1, Hiemke C3, Schönfeldt-Lecuona C1. J Clin Pharmacol. 2015 Oct 16. doi: 10.1002/jcph.662. [Epub ahead of print]
Drug-induced liver injury is a major problem of pharmacotherapy and is also frequent with antidepressive psychopharmacotherapy. However, there are only few studies using a consistent methodologic approach to study hepatotoxicity of a larger group of antidepressants. We performed a quantitative signal detection analysis using data from the Uppsala Monitoring Centre from the WHO that records adverse drug reaction (ADR)-data from worldwide sources; we retrieved substance- and country-specific (Australia, France, Germany, Italy, Spain, UK, and USA) ADR-data and calculated reporting odds ratios as measures for disproportionality within a case/non-case approach. To allow for identification of agents that cause severe forms of hepatotoxic ADR we used two different terms of the MeDRA ("Drug related hepatic disorders - comprehensive search" [DRHD-CS] and "… - severe events only" [DRHD-SEO]). Distribution of signals was heterogeneous throughout the different datasets and consistent findings were present only for few substances: agomelatine and tianeptine as well as both positive control agents (amineptine, nefazodone) generated signals related to DRHD-CS and DRHD-SEO in all analysed datasets.
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CAS 82752-99-6 Nefazodone hydrochloride

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