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Nefazodone information


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
  • N06AX06 (WHO)
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
  • 83366-66-9 checkY
    82752-99-6 (hydrochloride)
PubChem CID
  • 4449
IUPHAR/BPS
  • 7247
DrugBank
  • DB01149 checkY
ChemSpider
  • 4294 checkY
UNII
  • 59H4FCV1TF
KEGG
  • D08257 checkY
ChEBI
  • CHEBI:7494 checkY
ChEMBL
  • ChEMBL623 checkY
CompTox Dashboard (EPA)
  • DTXSID2023357 Edit this at Wikidata
Chemical and physical data
FormulaC25H32ClN5O2
Molar mass470.01 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 checkY
  • Key:VRBKIVRKKCLPHA-UHFFFAOYSA-N checkY
  (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treatment of depression and for other uses.[4][5][6][7] Nefazodone is still available in the United States,[8] but was withdrawn from other countries due to rare liver toxicity. The medication is taken by mouth.[9]

Side effects of nefazodone include dry mouth, sleepiness, nausea, dizziness, blurred vision, weakness, lightheadedness, confusion, and postural low blood pressure, among others.[9] 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.[9] 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][10][11] Generic versions were introduced in 2003.[12] Serious liver toxicity was first reported with nefazodone in 1998, and it was withdrawn from most markets by 2004.[11][13] 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. ^ Cite error: The named reference Teva Nefazodone Statement was invoked but never defined (see the help page).
  9. ^ a b c "Serzone (Nefazodone): Side Effects, Interactions, Warning, Dosage & Uses". RxList. January 2005. Archived from the original on 6 June 2017. Retrieved 3 June 2017.
  10. ^ Cite error: The named reference pmid8748566 was invoked but never defined (see the help page).
  11. ^ a b 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.
  12. ^ "Nefazodone". Drug Patent Watch. Archived from the original on 27 January 2018. Retrieved 3 June 2017.
  13. ^ Cite error: The named reference CBS2004 was invoked but never defined (see the help page).
  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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Nefazodone

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Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant medication which is used in the...

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Hydroxynefazodone

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antidepressant nefazodone. It has similar biological activity and a similar elimination half-life (1.5 to 4 hours) to those of nefazodone, and may contribute...

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Triazoledione

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metabolite of the antidepressant nefazodone. It is active, but with substantially reduced potency compared to nefazodone (approximately one-seventh). As...

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List of antidepressants

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Toludesvenlafaxine (Ruoxinlin) Nefazodone (Serzone) Vilazodone (Viibryd) Vortioxetine (Trintellix, Brintellix) Nefazodone (Dutonin, Nefadar, Serzone) –...

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Atypical antidepressant

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antidepressants include agomelatine, bupropion, iprindole, mianserin, mirtazapine, nefazodone, opipramol, tianeptine, and trazodone. The agents vilazodone and vortioxetine...

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Spontaneous orgasm

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rasagiline), serotonin antagonists and reuptake inhibitors (SARIs) (e.g., nefazodone), psychostimulants (e.g., methylphenidate, dextroamphetamine), typical...

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Ketamine

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Thiethylperazine Trazpiroben Trimethobenzamide Antidepressants: Amoxapine Nefazodone Opipramol Propiomazine Trimipramine Others: 3-PPP Alpiropride Azapride...

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MDMA

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Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics...

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LSD

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Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Silodosin...

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Sedative

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Desipramine (Norpramin) Doxepin Imipramine (Tofranil) Mirtazapine (Remeron) Nefazodone Nortriptyline (Pamelor) Trazodone (Desyrel) Trimipramine (Surmontil) Antipsychotics...

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Rilmenidine

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Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Silodosin...

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Cocaine

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Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol...

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Dopamine reuptake inhibitor

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clinically-relevant: adrafinil, armodafinil, bupropion, mazindol, modafinil, nefazodone, sertraline, and sibutramine. The following drugs are or have been clinically...

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Sertraline

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sertraline is similar in efficacy against depression to moclobemide, nefazodone, escitalopram, bupropion, citalopram, fluvoxamine, paroxetine, venlafaxine...

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Fluoxetine

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SARIsTooltip Serotonin antagonist and reuptake inhibitors Etoperidone Nefazodone Trazodone SMSTooltip Serotonin modulator and stimulators Vilazodone Vortioxetine...

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Lorpiprazole

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antagonist and reuptake inhibitor (SARI) in the same group as trazodone, nefazodone, and etoperidone. Acaprazine Enpiprazole Mepiprazole Tolpiprazole Elks...

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Brazilian Controlled Drugs and Substances Act

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authorization only. Moclobemide Molnupiravir Moperone Naloxone Naltrexone Nefazodone Nialamide Isobutyl nitrite Nomifensine Nortriptyline Noxiptiline Olanzapine...

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Etoperidone

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was never marketed. It is a phenylpiperazine related to trazodone and nefazodone in chemical structure and is a serotonin antagonist and reuptake inhibitor...

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Phenylpiperazine

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LASSBio-724 LASSBio-729 [66307-58-2] LASSBio-730 McN 261 [1044-59-3] Nefazodone Niaprazine Oxypertine PD-158771 [189152-50-9] PO-219 Trazodone WIN 18...

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Methylphenidate

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Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol...

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Tramadol

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Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol...

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Serotonin antagonist and reuptake inhibitor

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Etoperidone (Axiomin, Etonin) Lorpiprazole (Normarex) Mepiprazole (Psigodal) Nefazodone (Serzone, Nefadar) Trazodone (Desyrel) Vilazodone (Viibryd) – a related...

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Dapoxetine

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Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol...

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Alprazolam

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erythromycin, norfluoxetine, fluvoxamine, itraconazole, ketoconazole, nefazodone, propoxyphene, and ritonavir delay the hepatic clearance of alprazolam...

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ATC code N06

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Tryptophan N06AX03 Mianserin N06AX04 Nomifensine N06AX05 Trazodone N06AX06 Nefazodone N06AX07 Minaprine N06AX08 Bifemelane N06AX09 Viloxazine N06AX10 Oxaflozane...

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Triazolam

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cimetidine, diltiazem, fluconazole, grapefruit juice, isoniazid, itraconazole, nefazodone, rifampicin, ritonavir, and troleandomycin. Triazolam should not be administered...

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Citalopram

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SARIsTooltip Serotonin antagonist and reuptake inhibitors Etoperidone Nefazodone Trazodone SMSTooltip Serotonin modulator and stimulators Vilazodone Vortioxetine...

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Serotonin receptor antagonist

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and Alpha 1 (A1) adrenoreceptors. Risperidone antipsychotic Trazodone Nefazodone Another subclass consists of drugs selectively acting at the 5-HT3 receptors...

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