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Nefazodone

Names

[ CAS No. ]:
83366-66-9

[ 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