Mr. Ibrahem/Nefazodone
Clinical data
Trade namesSerzone, Dutonin, Nefadar, others
Other namesBMY-13754-1; MJ-13754-1
AHFS/Drugs.comMonograph
MedlinePlusa695005
Pregnancy
category
  • C
Routes of
administration
By mouth
Drug classAntidepressant[1]
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20% (variable)[2]
Protein binding99% (loosely)[2]
MetabolismLiver (CYP3A4, CYP2D6)[3]
MetabolitesHydroxynefazodone[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
  • 1-(3-[4-(3-chlorophenyl)piperazin-1-yl]propyl)-3-ethyl-4-(2-phenoxyethyl)-1H-1,2,4-triazol-5(4H)-one
Chemical and physical data
FormulaC25H32ClN5O2
Molar mass470.01 g·mol−1
3D model (JSmol)
  • Clc4cccc(N3CCN(CCCN1/N=C(\N(C1=O)CCOc2ccccc2)CC)CC3)c4
  • 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 under various brand names, is a medication primarily used to treat major depressive disorder.[1] Other uses include aggressive behavior and panic disorder.[4] It is taken by mouth.[1]

Common side effects include sleepiness, dry mouth, nausea, constipation, blurry vision, and confusion.[1] Other side effects may include liver problems, suicide, bipolar disorder, seizures, and priapism.[1] Safety in pregnancy is unclear.[5] How it works in not entirely clear but may involved effects on 5-HT and norepinephrine within the brain.[2]

Nefazodone was patented in 1982 and approved for medical use in the United States in 1988.[4][6] It is available as a generic medication.[1] In the United States it costs about 260 USD per month as of 2021.[7] It is no longer commonly used due to concerns with liver problems.[4] It was removed from the market in Europe, Canada, and Australia as of 2004.[8]

References edit

  1. ^ a b c d e f g h i "Nefazodone Monograph for Professionals". Drugs.com. Archived from the original on 27 February 2021. Retrieved 12 November 2021.
  2. ^ a b c d e f g h i j Alan F. Schatzberg, M.D.; Charles B. Nemeroff, M.D., Ph.D. (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition. American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. ^ a b Gian Maria Pacifici; Olavi Pelkonen (24 May 2001). Interindividual Variability in Human Drug Metabolism. CRC Press. pp. 103–. ISBN 978-0-7484-0864-1. Archived from the original on 6 August 2020. Retrieved 20 October 2021.
  4. ^ a b c "Nefazodone". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. Archived from the original on 2021-05-06. Retrieved 2021-11-12.
  5. ^ "Nefazodone (Serzone) Use During Pregnancy". Drugs.com. Archived from the original on 29 November 2020. Retrieved 12 November 2021.
  6. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 857–. ISBN 978-1-4757-2085-3. Archived from the original on 6 August 2020. Retrieved 20 October 2021.
  7. ^ "Nefazodone Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 7 March 2021. Retrieved 12 November 2021.
  8. ^ Cosgrove-Mather, Bootie (April 15, 2004). "Anti-Depressant Taken Off Market". CBS News. Archived from the original on December 2, 2020. Retrieved October 20, 2021.