Nefazodone

Nefazodone
Clinical data
Trade names	Serzone, Dutonin, Nefadar, others
Other names	BMY-13754-1; MJ-13754-1; MJ-13754; MS-13754
AHFS/Drugs.com	Monograph
MedlinePlus	a695005
Pregnancy; category	C;
Routes of; administration	By mouth
ATC code	N06AX06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	20% (variable)
Protein binding	99% (loosely)
Metabolism	Liver (CYP3A4, CYP2D6)
Metabolites	• Hydroxynefazodone; • mCPPTooltip meta-Chlorophenylpiperazine; • p-Hydroxynefazodone; • Triazoledione
Elimination half-life	• Nefazodone: 2–4 hours; • Hydroxynefazodone: 1.5–4 hours; • Triazoledione: 18 hours; • mCPPTooltip meta-Chlorophenylpiperazine: 4–8 hours
Excretion	Urine: 55%; Feces: 20–30%
Identifiers
	IUPAC name 1-(3-[4-(3-chlorophenyl)piperazin-1-yl]propyl)-3-ethyl-4-(2-phenoxyethyl)-1H-1,2,4-triazol-5(4H)-one;
CAS Number	83366-66-9 ; 82752-99-6 (hydrochloride);
PubChem CID	4449;
IUPHAR/BPS	7247;
DrugBank	DB01149 ;
ChemSpider	4294 ;
UNII	59H4FCV1TF;
KEGG	D08257 ;
ChEBI	CHEBI:7494 ;
ChEMBL	ChEMBL623 ;
CompTox Dashboard (EPA)	DTXSID2023357 ;
Chemical and physical data
Formula	C25H32ClN5O2
Molar mass	470.01 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc4cccc(N3CCN(CCCN1/N=C(\N(C1=O)CCOc2ccccc2)CC)CC3)c4;
	InChI InChI=1S/C25H32ClN5O2/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 ; Key:VRBKIVRKKCLPHA-UHFFFAOYSA-N ;
	(verify)

Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant medication which is used in the treatment of depression and for other uses. Nefazodone is still available in the United States, but was withdrawn from other countries due to rare liver toxicity. The medication is taken by mouth.

Side effects of nefazodone include dry mouth, sleepiness, nausea, dizziness, blurred vision, weakness, lightheadedness, confusion, and postural low blood pressure, among others. Rarely, nefazodone can cause serious liver damage, with an incidence of death or liver transplantation of about 1 in every 250,000 to 300,000 patient years. Nefazodone is a phenylpiperazine compound and is related to trazodone. It has been described as a serotonin antagonist and reuptake inhibitor (SARI) due to its combined actions as a potent antagonist of the serotonin 5-HT_2A and 5-HT_2C receptors and weak serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).

Nefazodone was introduced for medical use in 1994. Generic versions were introduced in 2003. Serious liver toxicity was first reported with nefazodone in 1998, and it was withdrawn from most markets by 2004. However, as of 2023, it continues to be available in the United States in generic from one manufacturer, Teva Pharmaceuticals and is manufactured in Israel.

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