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Systematic (IUPAC) name
(E)-5-methoxy-1-[4-(trifluoromethyl)phenyl]pentan-1-one O-2-aminoethyl oxime
Clinical data
  • C
Routes of
Legal status
Legal status
Pharmacokinetic data
Bioavailability 77%
Metabolism Hepatic
Biological half-life 15.6 hours
Excretion Renal
CAS Number 54739-18-3
ATC code N06AB08 (WHO)
PubChem CID 5324346
DrugBank APRD00425
ChemSpider 4481878
Chemical data
Formula C15H21F3N2O2
Molar mass 318.335[[Script error: No such module "String".]]
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Fluvoxamine (brand name Luvox, earlier also Fevarin) is an antidepressant which functions as a selective serotonin reuptake inhibitor (SSRI). Fluvoxamine was first approved by the U.S. Food and Drug Administration (FDA) in 1993 for the treatment of obsessive compulsive disorder (OCD).[1] Fluvoxamine CR (controlled release) is approved to treat social anxiety disorder.[2] Fluvoxamine is also prescribed to treat major depression and anxiety disorders, such as generalized anxiety disorder (GAD), panic disorder, and post-traumatic stress disorder (PTSD).[3]


Fluvoxamine was developed by Solvay Pharmaceuticals and was the first non-TCA drug approved by the U.S. Food and Drug Administration (FDA) specifically for the treatment of OCD.[4] It was one of the first SSRI antidepressants to be launched (1984 in Switzerland), and following its FDA approval in 1993, it was launched in the U.S. in December 1994, Australia in February 1999 and Japan in June 1999.[5]

At the end of 1995, more than 10 million patients worldwide had been treated with fluvoxamine.[6]

Fluvoxamine was the first SSRI to be registered for the treatment of obsessive compulsive disorder in children by the FDA in 1997.[7]

Fluvoxamine was the first drug approved for the treatment of social anxiety disorder in Japan in 2005.[8]

In 1999, fluvoxamine came under great public scrutiny after it was discovered that Eric Harris, one of the two teenage shooters involved in the Columbine High School massacre, had been taking the drug. Many immediately pointed fingers at fluvoxamine and its manufacturer Solvay Pharmaceuticals.[9] Sales fell, and Solvay withdrew the medication from the U.S. market in 2002.[10]

In 2007, Solvay re-introduced Luvox to the U.S., which is now manufactured by Palo Alto, California-based Jazz Pharmaceuticals, Inc. A generic version of Luvox is available from IVAX Pharmaceuticals, Inc.

On February 28, 2008, the FDA approved a controlled-release formulation of fluvoxamine, to be marketed as Luvox CR.[11][12]


Fluvoxamine is widely prescribed to treat major depressive disorder, and anxiety disorders such as obsessive compulsive disorder (OCD), generalized anxiety disorder (GAD), panic disorder, social phobia, and post-traumatic stress disorder (PTSD). Fluvoxamine is indicated for children and adolescents with OCD,[13] and the CR form is also indicated for social anxiety disorder.[2]


Fluvoxamine may help in the treatment of Irritable Bowel Syndrome.[14]

Side effects

Luvox 100 mg scored tablets (AU)

Side effects most commonly observed with fluvoxamine include nausea, vomiting, drowsiness, difficulty sleeping, dizziness, nervousness, feeling anxious, dry mouth, abdominal pain, constipation, diarrhea, heart burn, loss of appetite, muscle weakness, pins and needles, abnormal taste, headache, faster heart beat, sweating, weight gain, weight loss or unusual bruising. Other side effects which are observed more frequently in children include abnormal thoughts or behaviour, cough, increased period pain, nose bleeds, increased restlessness, infection and sinusitis.[15][16]

Sexual side effects with fluvoxamine are less pronounced than with other SSRIs.[17][18][19]


Fluvoxamine is a potent and selective serotonin reuptake inhibitor with approximately 100-fold affinity for the serotonin transporter over the norepinephrine transporter. It has negligible affinity for the dopamine transporter or any other receptor, with the sole exception of the σ1 receptor. It behaves as a potent agonist at this receptor and has the highest affinity of any SSRI for doing so. This may contribute to its antidepressant and anxiolytic effects. Indeed, other SSRIs which also act as σ1 receptor agonists, such as sertraline and escitalopram (not verified but likely to be), display enhanced antidepressant efficacy.[20] suggesting that it may have particular benefits in the treatment of depressed patients who show features of anxiety/stress and for whom memory impairment is particularly undesirable (such as in depressed elderly patients, and also in treating psychotic depression).[21] In fact, the TCA opipramol, a σ1 receptor agonist without effects on the serotonin, dopamine, or norepinephrine systems, has considerable antidepressant and efficacy in its own right.



The oral absorption of fluvoxamine is equal to or more than 94%.


The plasma protein binding is only about 76%.


Fluvoxamine is strongly metabolized in the liver, mostly by the processes of oxidative demethylation(1) and deaminiation(2), which, respectively, create the three metabolites: fluvoxamine acid(by mechanism 1), it's N-acytylated analog(1), fluvoxethanol(2), of which only the first has been shown to have an affinity as a SERT inhibitor, roughly 100% - 200%, or 1-2 orders of magnitude, less potent than the active parent compound.[22]

Radio-labeled administration of a dose of fluvoxamine produced nine identifiable metabolites, constituting 85% of the absorbed dosage. Of this base parent-metabolic percentage, 60% of the isolate was empirically proven to be fluvoxamine acid, and it's N-acytylated analog, 10% fluvoxethanol, logically deducible is that the additional 15% consisted of the remaining six identified metabolites of the parent compound.[22]


Fluvoxamine has the shortest half-life of all SSRIs; its mean serum half-life is 15.6 hours.[23]

Drug interactions

Fluvoxamine has a low potential for the drug interactions which are based on inhibition of enzyme Cytochrome P450 CYP2D6. Fluvoxamine shows the least interaction of the SSRIs, in regard to this specific enzyme.[24][25][26] Naturally the other SSRIs which are metabolized by CYP2D6 will have more CYP2D6-based interactions with TCAs, antiarrhythmics, B-blockers, phenytoin, opioids and neuroleptics.

Fluvoxamine does, however, inhibit cytochrome P450 enzyme CYP1A2, which metabolises agomelatine, caffeine, clozapine, haloperidol, phenacetin, tacrine, theophylline, and olanzapine. These substances can cause increased serum levels when administered together with fluvoxamine. Of major concern is the fact that the polycyclic aromatic hydrocarbons found in tobacco smoke are potent inducers of CYP1A2 so that smokers may require significant modification of medication dosage.[27] A recent warning has been published regarding potentially serious interaction with tizanidine, based on CYP1A2 metabolism.[28]

Fluvoxamine inhibits metabolism of diazepam and phenytoin via CYP2C19 and metabolism of aripiprazole, chlorpromazine, clozapine, haloperidol, olanzapine, perphenazine, risperidone, thioridazine and zuclopenthixol via CYP2D6 as well as of aripiprazole, clozapine, haloperidol, quetiapine, risperidone and ziprasidone via CYP3A4.[29]

The plasma protein binding of fluvoxamine is about 77%. Drugs with low protein binding are less likely to displace other protein bound drugs, and therefore have a lower potential to cause protein binding-related drug interactions.

Fluvoxamine also inhibits CYP2C9.[22][30]


Fluvoxamine is one of the few SSRIs to have a monocyclic structure. 500px[31]

See also


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External links

de:Fluvoxamin es:Fluvoxamina fa:فلووکسامین fr:Fluvoxamine it:Fluvoxamina hu:Fluvoxamin ja:フルボキサミン no:Fluvoksamin pl:Fluwoksamina pt:Fluvoxamina ru:Флувоксамин sv:Fluvoxamin

  1. ToddlerTime.com | What is Luvox?
  2. 2.0 2.1 Stahl, S. Stahl's Essential Psychopharmacology: The Prescriber's Guide. Cambridge University Press. New York, NY. 2009. pp.215
  3. Karen J. McClellan, David P. Figgitt (Drugs October 2000). "Fluvoxamine An Updated Review of its Use in the Management of Adults with Anxiety Disorders". Adis Drug Evaluation. 60 (4): 925–954.  Check date values in: |date= (help)
  4. Pharmalot | BrainPhysics.com| Medications for OCD
  5. Solvay Pharmaceuticals Australia | Luvox
  6. Fluvoxamine Product Monograph. 1999.  Missing or empty |title= (help)
  7. "Luvox Approved For Obsessive Compulsive Disorder in Children and Teens". Http://www.pslgroup.com/dg/2261a.htm.  External link in |journal= (help)
  8. "Solvay's Fluvoxamine maleate is first drug approved for the treatment of social anxiety disorder in Japan". Http://www.solvaypress.com/pressreleases/0,,33713-2-83,00.htm.  External link in |journal= (help)
  9. "Judge: Seal Columbine papers for 25 years". The Denver Post. January 26, 2007. Retrieved 2008-03-03. 
  10. "Solvay Pharmaceuticals, Inc. Withdraws LUVOX". Http://www.solvaypharmaceuticals-us.com/newsroom/pressreleases/0,,14517-2-0,00.htm.  External link in |journal= (help)
  12. "Luvox CR" (PDF). Retrieved 2008-02-21.  Text " Prescribing Info " ignored (help)
  13. Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  14. Emmanuel; Lydiard, RB; Crawford, M; et al. (1997). "Treatment of Irritable Bowel Syndrome with Fluvoxamine". Am J Psychiatry. 154 (5): 711–712. PMID 9137135. 
  15. Better Health Channel | Consumer Medicine Information
  16. myDr | Consumer Medicine Information
  17. Hengeveld VW, Waldinger MD; Hengeveld, MW; Zwinderman, AH; Olivier, B; et al. (1998). "Effect of SSRI antidepressants on ejaculation: a double blind, randomised, placebo-controlled study with fluoxetine, fluvoxamine, paroxetine and sertraline". Journal of Clinical Psychopharmacology. 18 (4): 274–281. doi:10.1097/00004714-199808000-00004. PMID 9690692. 
  18. Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  19. http://www.ncbi.nlm.nih.gov/pubmed/19440080
  20. Hashimoto K, Narita N; Hashimoto, K; Tomitaka, S; Minabe, Y; et al. (1996). "Interactions of selective reuptake inhibitors with subtypes of sigma receptor in rat brain". Eur J Pharmacol. 307 (1): 117–9. doi:10.1016/0014-2999(96)00254-3. PMID 8831113. 
  21. Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  22. 22.0 22.1 22.2 "Luvox Tablets (Fluvoxamine Maleate) Drug Information: Uses, Side Effects, Drug Interactions and Warnings at RxList". Retrieved 2009-02-17. 
  23. Center for Drug Evaluation and Research, (2000). Fluvoxamine Maleate Tablets. Application Number: 75901, Retrieved July 28, 2008, from http://www.fda.gov/cder/foi/anda/2000/75901_Fluvoxamine%20Maleate_Prntlbl.pdf
  24. P., Baumann (1996). "Pharmacokinetic-pharmacodynamic relationship of the Selective serotonin reuptake inhibitors". Clinical Pharmacokinetics. 31 (6): 444–469. doi:10.2165/00003088-199631060-00004. PMID 8968657. 
  25. Gill HS, DeVane CL (1997). "Clinical Pharmacokinetics of Fluvoxamine: applications to dosage regime design". Journal of Clinical Psychiatric. 58 (Suppl 5): 7–14. 
  26. DeVane, CL (1998). "Translational pharmacokinetics: current issues with newer antidepressants". Depression and Anxiety. 8 (Suppl 1): 64–70. doi:10.1002/(SICI)1520-6394(1998)8:1+<64::AID-DA10>3.0.CO;2-S. PMID 9809216. 
  27. Kroom, Lisa A. (10-01-2007). "Drug Interactions With Smoking". Am J Health-Syst Pharm. Medscape: American Society of Health-System Pharmacists. 64 (18): 1917–1921. doi:10.2146/ajhp060414. PMID 17823102. Retrieved 2008-01-31.  Check date values in: |date= (help)
  28. Waknine, Yael (April 13, 2007). "Prescribers Warned of Tizanidine Drug Interactions". Medscape News. Medscape. Retrieved 2008-02-01. 
  29. Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  30. "Brain Elimination Half-Life of Fluvoxamine". 
  31. A. Korkuczanski (1958). Przemysł chemiczny, 37, 162.