Nefazodone

Names

[ Name ]:
Nefazodone

[Synonym ]:
[14C]-Nefazodone hydrochloride
Nefazodonum
Nefazodonum [Latin]
2-[3-[4-(3-chlorophenyl)-1-piperazinyl]-propyl-]5-ethyl-2,4-dihydro-4-(2-phenoxy-ethyl)-3H-1,2,4-triazol-3-one
2-<3-<4-(3-chlorophenyl)-1-piperazinyl>propyl>-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazolin-3-one
Nefazodone Hcl
2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-5-ethyl-4-(2-phenoxyethyl)-1,2,4-triazol-3-one
Nefazodona
Nefazodone (INN)
Nefazodona [Spanish]
2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one
UNII-59H4FCV1TF
MFCD00935760

Biological Activity

[Description]:

Nefazodone is an orally active phenylpiperazine antidepressant. Nefazodone can potently and selectively block postsynaptic 5-HT2A receptors, and moderately inhibit 5-HT and noradrenaline reuptake. Nefazodone can also relieve the adverse effects of stress on the the immune system of mice. Nefazodone has a high affinity for CYP3A4 isoenzyme, which indicates that it has certain risk of drug-drug interaction[1][2][3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT receptor, Noradrenaline, CYP3A4[1]

[In Vitro]

Nefazodone collapses mitochondrial membrane potential, and imposes oxidative stress, as detected via glutathione depletion, leading to cell death[2]. Nefazodone (200 μM; 24 h) depletes 100% of ATP in both, glucose and galactose-grown HepG2 cells[2]. Nefazodone (6.25, 12.5 and 25 μM; 0-120 min) profoundly inhibits oxygen consumption (OCR) in HepG2[2].

[In Vivo]

Nefazodone (10 mg/kg; s.c.; for 16 days) is effective to counter the adverse effects of stress on the the immune system of mice[3]. Animal Model: Female BALB/c mice (7-12 weeks old; stress model; subjected to a broad band noise at 100 dB daily for 5 s every minute during a 1- or 3-h period around midnight)[3] Dosage: 10 mg/kg Administration: s.c.; for 16 days Result: Attenuated the reduction of thymus, spleen and peripheral blood cellularity caused by stress.

Chemical & Physical Properties

[ Melting Point ]:
180-182°C

[ Molecular Formula ]:
C₂₅H₃₂ClN₅O₂

[ Molecular Weight ]:
470.00700

[ Exact Mass ]:
469.22400

[ PSA ]:
55.53000

[ LogP ]:
3.55480

[ Water Solubility ]:
DMSO: ~11 mg/mL at 60 °C

Safety Information

[ Safety Phrases ]:
S22-S24/25

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.