Nefazodone

Nefazodone
Clinical data
Trade namesSerzone, Dutonin, Nefadar, others
Other namesBMY-13754-1; MJ-13754-1; MJ-13754; MS-13754
AHFS/Drugs.comMonograph
MedlinePlusa695005
Pregnancy
category
  • C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[1]
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20% (variable)[2]
Protein binding99% (loosely)[2]
MetabolismLiver (CYP3A4, CYP2D6)[3]
Metabolites• Hydroxynefazodone[2]
• mCPPTooltip meta-Chlorophenylpiperazine[2]
• p-Hydroxynefazodone[3]
• Triazoledione[2]
Elimination half-life• Nefazodone: 2–4 hours[2]
• Hydroxynefazodone: 1.5–4 hours[2]
• Triazoledione: 18 hours[2]
• mCPPTooltip meta-Chlorophenylpiperazine: 4–8 hours[2]
ExcretionUrine: 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H32ClN5O2
Molar mass470.01 g·mol−1
3D model (JSmol)
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 Y
  • Key:VRBKIVRKKCLPHA-UHFFFAOYSA-N Y
  (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antidepressant medication which is used in the treatment of depression and for other uses.[4][5][6][7] Nefazodone was withdrawn in most countries by 2004[8][9] (due to liver toxicity[10]), but was, as of December 2021, still available in the United States.[11] The medication is taken by mouth.[10]

Side effects of nefazodone include dry mouth, sleepiness, nausea, dizziness, blurred vision, weakness, lightheadedness, confusion, and postural low blood pressure, among others.[10] 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.[10] 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-HT2A and 5-HT2C receptors and weak serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).

Nefazodone was introduced for medical use in 1994.[7][12][8] Generic versions were introduced in 2003.[13] Serious liver toxicity was first reported with nefazodone in 1998, and it was withdrawn from most markets by 2004.[8][9] However, as of 2023, it continues to be available in the United States in generic from one manufacturer, Teva Pharmaceuticals[14] and is manufactured in Israel.[15]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ a b c d e f g h i Schatzberg AF, Nemeroff CB (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition. American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.
  3. ^ a b Pacifici GM, Pelkonen O (24 May 2001). Interindividual Variability in Human Drug Metabolism. CRC Press. pp. 103–. ISBN 978-0-7484-0864-1.
  4. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  7. ^ a b "Drugs of Current Interest: Nefazodone". WHO Pharmaceuticals Newsletter (1). 2003. Archived from the original on April 3, 2015.
  8. ^ a b c Babai S, Auclert L, Le-Louët H (2021). "Safety data and withdrawal of hepatotoxic drugs". Therapie. 76 (6): 715–723. doi:10.1016/j.therap.2018.02.004. PMID 29609830.
  9. ^ a b Cite error: The named reference CBS2004 was invoked but never defined (see the help page).
  10. ^ a b c d "Serzone (Nefazodone): Side Effects, Interactions, Warning, Dosage & Uses". RxList. January 2005. Archived from the original on 6 June 2017. Retrieved 3 June 2017.
  11. ^ Cite error: The named reference Teva Nefazodone Statement was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference pmid8748566 was invoked but never defined (see the help page).
  13. ^ "Nefazodone". Drug Patent Watch. Archived from the original on 27 January 2018. Retrieved 3 June 2017.
  14. ^ "Drugs@FDA: FDA-Approved Drugs". Archived from the original on 2021-08-27. Retrieved 2023-02-11.
  15. ^ "DailyMed - NEFAZODONE HYDROCHLORIDE tablet". dailymed.nlm.nih.gov. Archived from the original on 2016-09-16. Retrieved 2023-10-29.
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