Nefazodone

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Structural formula
Structural formula of nefazodone
General
Non-proprietary name Nefazodone
other names

1- {3- [4- (3-chlorophenyl) piperazin-1-yl] propyl} -3-ethyl-4- (2-phenoxyethyl) -4,5-dihydro-1,2,4-triazole-5- on

Molecular formula C 25 H 32 ClN 5 O 2
External identifiers / databases
CAS number
PubChem 4449
ChemSpider 4294
DrugBank DB01149
Wikidata Q416632
Drug information
ATC code

N06 AX06

Drug class

Antidepressants

Mechanism of action

Serotonin norepinephrine reuptake inhibitors

properties
Molar mass 470.01 g · mol -1
Physical state

firmly

Melting point
  • 83-84 ° C (nefazodone)
  • 175–187 ° C (nefazodone hydrochloride)
solubility
  • almost insoluble in water (nefazodone hydrochloride)
  • soluble in DMF [10 g · l −1 , (nefazodone · hydrochloride) ]
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Hydrochloride

no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nefazodone is one belonging to the class of antidepressants dualserotonergen (DSA) antidepressant . It is a phenylpiperazine derivative that is structurally and partly also in its mode of action similar to the long-known antidepressant trazodone .

Mode of action

The antidepressant effect of nefazodone occurs through two mechanisms. On the one hand it blocks the serotonin 5-HT 2A receptor and on the other hand, to a lesser extent, also the presynaptic reuptake of serotonin.

Nefazodone has no significant affinity for α- or β- adrenoceptor and histamine , dopamine and acetylcholine receptors .

history

In Germany it was sold by Bristol-Myers Squibb from 1997 under the name Nefadar , in the USA it was available under the name Serzone .

The drug was withdrawn from the market in 2003 because of a few cases of severe liver failure .

Individual evidence

  1. ↑ a b entry on nefazodone. In: Römpp Online . Georg Thieme Verlag, accessed on December 22, 2014.
  2. ↑ a b c d data sheet Nefazodone hydrochloride from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

Web links