Fluvoxamine

Brand names: Luvox®

Chemical formula:

Drug Forms:
• Fluvoxamine tablets (below)
• Fluvoxamine extended-release capsules
• Fluvoxamine Maleate Oral capsule, extended-release
• Fluvoxamine Maleate Oral tablet

Español:
• Tabletas de fluvoxamina
• Maleato de fluvoxamina, Cápsula oral de liberación prolongada
• Fluvoxamina Maleato, Tableta oral

Fluvoxamine tablets

What are fluvoxamine tablets?

FLUVOXAMINE (Luvox®) helps people with an obsessive-compulsive disorder. It relieves the anxiety and unpleasant thoughts that make a person repeat everyday tasks (like hand-washing). Fluvoxamine is also used as an antidepressant, and may be used to treat other conditions such as panic disorder, premenstrual syndrome, or traumatic stress. Generic fluvoxamine tablets are available.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• heart disease
• history of manic illness
• liver disease
• seizures (convulsions)
• suicidal thoughts
• tobacco smoker
• an unusual or allergic reaction to fluvoxamine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take fluvoxamine tablets by mouth. Follow the directions on the prescription label. Swallow the tablets with a drink of water. You may take fluvoxamine with or without food. Take your doses at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your prescriber's advice.

What if I miss a dose?

What drug(s) may interact with fluvoxamine?

Fluvoxamine has the potential to interact with a variety of medications, check with your healthcare professional. The following list contains some of these interactions.

Do not take fluvoxamine with any of the following medications:
• astemizole (Hismanal®)
• cisapride (Propulsid®)
• pimozide (Orap®)
• ramelteon (Rozerem™)
• terfenadine (Seldane®)
• thioridazine (Mellaril®)
• medicines called MAO inhibitors-phenelzine (Nardil®), tranylcypromine (Parnate®), isocarboxazid (Marplan®), selegiline (Eldepryl®)

Fluvoxamine may also interact with the following medications:
• alcohol
• amphetamine
• caffeine
• carbamazepine
• certain diet drugs (dexfenfluramine, fenfluramine, phentermine, sibutramine)
• cimetidine
• dextroamphetamine
• dextromethorphan
• diltiazem
• dofetilide
• doxercalciferol
• ergonovine
• grapefruit juice
• kava kava
• linezolid
• medications for the treatment of HIV infection or AIDS
• melatonin
• migraine headache medicines (almotriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan, dihydroergotamine, ergotamine, methysergide)
• medications for anxiety or sleep problems; examples include alprazolam or diazepam
• methylergonovine
• metoprolol
• other medicines used for mental problems like depression or psychosis
• paricalcitol
• propranolol
• sildenafil
• some medicines for the treatment of pain
• St. John's wort, Hypericum perforatum
• theophylline
• tizanidine
• valerian
• verapamil
• voriconazole
• warfarin

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, and herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking fluvoxamine?

Visit your prescriber or health care professional for regular checks on your progress. Continue to take your tablets even if you do not immediately feel better. It can take several weeks before you feel the full effect of fluvoxamine. If you get suicidal thoughts, extreme agitation, or inability to sleep or sit still, call your prescriber or health care professional at once.

If you have been taking fluvoxamine regularly for some time, do not suddenly stop taking it. You must gradually reduce the dose or your symptoms may get worse. Ask your prescriber or health care professional for advice.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how fluvoxamine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol can make you more drowsy and dizzy. Avoid alcoholic drinks.

Do not treat yourself for coughs, colds or allergies without asking your prescriber or health care professional for advice. Some ingredients can increase possible side effects.

In general, do not drink grapefruit juice if you are taking fluvoxamine. If you have been drinking grapefruit juice with fluvoxamine that was previously prescribed, discuss this with your health care provider. If you stop drinking grapefruit juice, your dose of fluvoxamine may need to be adjusted.

Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water will help.

If you are going to have surgery, tell your prescriber or health care professional that you are taking fluvoxamine.

What side effects may I notice from taking fluvoxamine?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• fast talking and excited feelings or actions that are out of control
• hallucination, loss of contact with reality
• irregular heartbeat (palpitations)
• muscle spasms or weakness
• seizures (convulsions)
• skin rash
• unusual tiredness or weakness
• vomiting

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• agitation or restlessness
• anxiety or nervousness
• daytime drowsiness
• diarrhea or constipation
• difficulty sleeping
• dry mouth
• headache
• increased sweating
• indigestion
• loss of appetite
• sexual difficulties (decreased sexual desire or ability)
• tremor (shaking)

Where can I keep my medicine?

Keep out of the reach of children in a container that small children cannot open.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

A selective serotonin reuptake inhibitor (SSRI) antidepressant.

The examples and perspective in this article may not represent a worldwide view of the subject. Please improve this article and discuss the issue on the talk page.

Fluvoxamine
Systematic (IUPAC) name
(Z)-5-methoxy-1-[4-(trifluoromethyl)phenyl]pentan-1-one O-2-aminoethyl oxime
Identifiers
CAS number	54739-18-3
ATC code	N06AB08
PubChem	5324346
DrugBank	APRD00425
ChemSpider	4481878
Chemical data
Formula	C15H21F3N2O2
Mol. mass	318.335
Pharmacokinetic data
Bioavailability	77%
Metabolism	Hepatic
Half life	15.6 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C
Legal status	Prescription Only (S4)(AU) ℞-only(US)
Routes	Oral
Y(what is this?)  (verify)

Fluvoxamine (Luvox) is an antidepressant which functions as a selective serotonin reuptake inhibitor and is predominantly used to treat obsessive–compulsive disorder.

Contents 1 History 2 Indications 2.1 Unapproved/off-label/investigational 3 Side effects 4 Chemistry 5 Pharmacology 6 Pharmacokinetics 6.1 Absorption 6.2 Distribution 6.3 Metabolism 6.4 Elimination 7 Drug interactions 8 Notes 9 External links

History

Fluvoxamine was one of the first of the SSRI antidepressants to be launched (1984, in Switzerland) and was developed by Solvay Pharmaceuticals. It was launched in the US in December 1994 and in Japan in June 1999. As of the end of 1995, more than 10 million patients worldwide have been treated with fluvoxamine.^[1]

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.^[2] Sales fell, and Solvay withdrew the medication from the U.S. market in 2002.^[3]

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

Fluvoxamine was the first SSRI to be registered for the treatment of obsessive–compulsive disorder in children by FDA in 1997.^[4]

Fluvoxamine was the first drug approved for the treatment of social anxiety disorder in Japan in 2005.^[5]

On February 28, 2008, the US FDA approved a controlled-release formulation of fluvoxamine, to be marketed as Luvox CR.^[6][7]

Indications

Fluvoxamine is widely prescribed to treat major depression, and anxiety disorders such as obsessive–compulsive disorder, Panic Disorder, Social Phobia, and Post-Traumatic Stress Disorder.^[8]

Fluvoxamine is indicated for children and adolescents with OCD.^[9]

Unapproved/off-label/investigational

Fluvoxamine is also used for the treatment of children and adolescents with social phobia, separation anxiety disorder, or generalized anxiety disorder.^[10]

Fluvoxamine may help in the treatment of Irritable Bowel Syndrome.^[11]

Side effects

Common side effects of fluvoxamine are: 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 observed more frequently in children are: abnormal thoughts or behaviour, cough, increased period pain, nose bleeds, increased restlessness, infection and sinusitis.^[12][13]

Sexual side effects with fluvoxamine are rare, unlike other SSRIs.^[14][15][16]

Chemistry

Luvox 100 mg film-coated scored tablets (AU)

Fluvoxamine is one of the few SSRIs to have a monocyclic structure.

Pharmacology

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 sigma-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 sigma-σ₁ receptor agonists, such as sertraline and escitalopram (not verified but likely to be), display enhanced antidepressant efficacy.^[17] 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).^[18] In fact, the TCA opipramol, which is a selective sigma-σ₁ receptor agonist, has considerable antidepressant and efficacy in its own right.

Pharmacokinetics

Absorption

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

Distribution

The plasma protein binding is only about 76%.

Metabolism

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. ^[19]

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. ^[19]

Elimination

Fluvoxamine has the shortest half-life of all SSRIs, its mean serum half-life is 15.6 hours.^[20]

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.^[21][22][23] Naturally the other SSRIs which are metabolized by CYP2D6 will have more CYP2D6-based interactions with TCAs, antiarrhythmics, B-blockers, phenytoin, opiates (eg. codeine, dextromethorphan, morphine, tramadol) and neuroleptics (eg. haloperidol, risperidone).

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.^[24] A recent warning has been published regarding potentially serious interaction with Tizanidine, based on CYP1A2 metabolism.^[25]

Fluvoxamine inhibits metabolism of diazepam and phenytoin via CYP2C19 and inhibits metabolism of aripiprazole, chlorpromazine, clozapine, haloperidol, olanzapine, perphenazine, risperidone, thioridazine and zuclopenthixol via CYP2D6 as well as inhibiting metabolism of aripiprazole, clozapine, haloperidol, quetiapine, risperidone and ziprasidone via CYP3A4.^[26]

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: CYP3A4, CYP2C9, and CYP2C19 ^{[19] [27]}

Notes

1. ^ Fluvoxamine Product Monograph. 1999. 
2. ^ "Judge: Seal Columbine papers for 25 years". The Denver Post. January 26, 2007. http://www.denverpost.com/golf/ci_5094436. Retrieved 2008-03-03. 
3. ^ "Solvay Pharmaceuticals, Inc. Withdraws LUVOX". http://www.solvaypharmaceuticals-us.com/newsroom/pressreleases/0,,14517-2-0,00.htm. 
4. ^ "Luvox Approved For Obsessive Compulsive Disorder in Children and Teens". Http://www.pslgroup.com/dg/2261a.htm. 
5. ^ "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. 
6. ^ "Jazz Pharmaceuticals press release, February 28, 2008 – FDA APPROVES LUVOX CR (FLUVOXAMINE MALEATE) EXTENDED-RELEASE CAPSULES FOR THE TREATMENT OF SOCIAL ANXIETY DISORDER (SAD) AND OBSESSIVE COMPULSIVE DISORDER (OCD)". http://www.jazzpharma.com/news.php?id=59. Retrieved 2008-03-14. 
7. ^ "PDF-Prescribing Info". http://www.luvoxcr.com/LUVOX-CR-PI.pdf. Retrieved 2008-02-21. 
8. ^ 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. 
9. ^ US-FDA Fluvoxamine Product Insert. March 2005. 
10. ^ John T Walker MD, Michael J. Labelarte MD et al. (April 26, 2001). "Fluvoxamine for the treatment of anxiety disorders in children and adolescents". The New England Journal of Medicine 344: 1279–1285. doi:10.1056/NEJM200104263441703. PMID 11323729. 
11. ^ Emmanuel, et al. (1997). "Treatment of Irritable Bowel Syndrome with Fluvoxamine". Am J Psychiatry 154: 711–712. 
12. ^ Consumer Medicine Information
13. ^ Consumer Medicine Information
14. ^ Hengeveld VW et al., Waldinger MD (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: 274–281. doi:10.1097/00004714-199808000-00004. 
15. ^ Riley, A.; R.T. Segraves (2006). "Treatment of Premature Ejaculation". Int J. Clin Pract. (Blackwell Publishing) 60 (6): 694–697. doi:10.1111/j.1368-5031.2006.00818.x. http://www.medscape.com/viewarticle/533889_print. Retrieved 2008-02-01. 
16. ^ http://www.ncbi.nlm.nih.gov/pubmed/19440080
17. ^ Hashimoto K et al., Narita N (1996). "Interactions of selective reuptake inhibitors with subtypes of sigma receptor in rat brain". Eur J Pharmacol 307: 117–9. doi:10.1016/0014-2999(96)00254-3. 
18. ^ C.Sandner, Carrasco JL (December 2005). "Clinical effects of pharmacological variations in selective serotonin reuptake inhibitors: an overview". International Journal of Clinical Practice 59 (12): 1428–1434. doi:10.1111/j.1368-5031.2005.00681.x. 
19. ^ ^{a b c} "Luvox Tablets (Fluvoxamine Maleate) Drug Information: Uses, Side Effects, Drug Interactions and Warnings at RxList". http://www.rxlist.com/luvox-drug.htm. Retrieved 2009-02-17. 
20. ^ 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
21. ^ P., Baumann (1996). "Pharmacokinetic-pharmacodynamic relationship of the Selective serotonin reuptake inhibitors". Clinical Pharmacokinetics 31: 444–469. doi:10.2165/00003088-199631060-00004. 
22. ^ Gill HS, DeVane CL (1997). "Clinical Pharmacokinetics of Fluvoxamine: applications to dosage regime design". Journal of Clinical Psychiatric 58 (Suppl 5): 7–14. 
23. ^ 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. 
24. ^ 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. http://www.medscape.com/viewarticle/562754_print. Retrieved 2008-01-31. 
25. ^ Waknine, Yael (April 13, 2007). "Prescribers Warned of Tizanidine Drug Interactions". Medscape News. Medscape. http://www.medscape.com/viewarticle/555194_print. Retrieved 2008-02-01. 
26. ^ Bondy, Brigitta; Illja Spellmann (2007). "Pharmacogenetics of Antipsychotics: Useful For the Clinician?". Curr Opin Psychiatry (Medscape: Lippincott Williams & Wilkins) 20 (1): 126–130. doi:10.1097/YCO.0b013e328017f69f. http://www.medscape.com/viewarticle/552100_print. Retrieved 2008-02-01. 
27. ^ "Brain Elimination Half-Life of Fluvoxamine". http://ajp.psychiatryonline.org/cgi/content/full/155/3/380. 

External links

• RxList.com – Fluvoxamine
• Drugs.com – Fluvoxamine

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v • d • e Serotonergics Receptor Ligands 5-HT1 5-HT1A Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Eptapirone • Gepirone • Ipsapirone • Perospirone • Tandospirone • Tiospirone • Zalospirone; Lysergamides: Dihydroergotamine • Ergotamine • Methysergide • LSD; Phenethylamines: MDA • MDMA; Piperazines: Eltoprazine • Flesinoxan • Flibanserin; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • DMT • Psilocin • Psilocybin • Rauwolscine • Yohimbine; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone; Others: 8-OH-DPAT • Befiradol • F-11440 • Lesopitron • Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • Osemozotan • Piclozotan • PRX-00023 • Repinotan • RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone • Xaliproden Antagonists: Beta Blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol; Piperazines: Nefazodone • Trazodone • WAY-100,135 • WAY-100,635; Others: AV965 • BMY-7378 • Dotarizine • GR-46611 • Isamoltane • Lecozotan • Methiothepin • MPPF • NAN-190 • Robalzotan • S-15535 • SB-649915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine 5-HT1B Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine • TFMPP; Triptans: Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-93,129 • CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline • Methiothepin; Tryptamines: Yohimbine; Others: AR-A000002 • GR-127,935 • Isamoltane • SB-216,641 • SB-224,289 • SB-236,057 5-HT1D Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633 Antagonists: Lysergamides: Metergoline • Methiothepin; Tryptamines: Rauwolscine • Yohimbine; Others: BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Ritanserin • Ziprasidone 5-HT1E Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Methiothepin 5-HT1F Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Methiothepin 5-HT2 5-HT2A Agonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD • Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-NBMD • 25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin • TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: AL-34662 • AL-37350A • PNU-22394 Antagonists: Atypical Antipsychotics: Amperozide • Aripiprazole • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline • Amoxapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: 5-I-R91150 • AC-90179 • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Fananserin • Flibanserin • Ketanserin • KML-010 • Lubazodone • Methiothepin • Nantenine • Pimavanserin • Pizotifen • Ritanserin • Sarpogrelate • Setoperone • Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine • Yohimbine 5-HT2B Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • DOB • DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT; Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175 Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine 5-HT2C Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Lorcaserin • MK-212 • PNU-22394 • Ro60-0175 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348 Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Trazodone; Others: Cinanserin • Cyproheptadine • Deramciclane • Dimebolin • Dotarizine • Eltoprazine • FR-260,010 • Ketanserin • Ketotifen • Methysergide • Pizotifen • Ritanserin • RS-102,221 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine 5-HT3 Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others: Chlorophenylbiguanide • RS-56812 • SR-57,227 • SR-57,227-A • YM-31636 Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron • Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron • Zacopride • Zatosetron; Atypical Antipsychotics: Clozapine • Olanzapine • Quetiapine; Tetracyclic Antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: ICS-205,930 • Lu AA21004 • MDL-72,222 • Memantine • Ricasetron 5-HT4 Agonists: Gastroprokinetic Agents: Cisapride • Metoclopramide • Mosapride • Prucalopride • Renzapride • Tegaserod • Zacopride; Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 • TD-5108 Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-67532 • SB-203,186 5-HT5 5-HT5A Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine • Dimebolin • Methiothepin • Ritanserin • SB-699,551 5-HT5B* Agonists: Lysergamides: Ergotamine • LSD Antagonists: Methiothepin * Note that the 5-HT5B receptor is not functional in humans. 5-HT6 Agonists: Lysergamides: Lisuride • LSD • Metergoline; Tryptamines: 5-CT • 5-MT • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-586,713 • WAY-181,187 • WAY-208,466 Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • Dimebolin • EGIS-12233 • GW-742,457 • Ketanserin • Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro 04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 5-HT7 Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT; Others: 8-OH-DPAT • AS-19 • Bifeprunox • LP-12 • LP-44 • Sarizotan Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical Antipsychotics: Amisulpride • Aripiprazole • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: EGIS-12233 • LY-215,840 • Mesulergine • Metergoline • Methiothepin • Pimozide • Ritanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507 Reuptake Inhibitors Plasmalemmal SERT Inhibitors Selective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine • Desmethylcitalopram • Desmethylsertraline • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Litoxetine • Lubazodone • Norfluoxetine • Paroxetine • RTI-353 • Sertraline • Vilazodone • Zimelidine; Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • NS-2359 • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine (Pyrilamine) • Pheniramine • Tripelennamine; Opioids: Meperidine (Pethidine) • Methadone • Propoxyphene • Tramadol; Others: Cocaine • Cyclobenzaprine (CBZ) • Dextromethorphan (DXM) • Mesembrine • Nefopam • SB-649,915 • Sibutramine • Ziprasidone TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing Agents Aminoindanes: Ethyltrifluoromethylaminoindane (ETAI) • Methylenedioxyaminoindane (MDAI) • Methylenedioxymethylaminoindane (MDMAI) • Methoxymethylaminoindane (MMAI) • Trifluoromethylaminoindane (TAI); Aminotetralins: 8-Hydroxydipropylaminotetralin (8-OH-DPAT); Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 4-Methylthioamphetamine (4-MTA) • 5-Aminopropyldihydrobenzofuran (5-APDB; 5-Desoxy-MDA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Brephedrone • Butylone • Chlorphentermine • Dibutylone • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenfluramine (Dexfenfluramine) • Flephedrone • Indanylamphetamine (IAP) • Lophophine (Homomyristicylamine) • Mephedrone • Methedrone • Methoxymethylamphetamine (MMA) • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Naphthylamphetamine (NAP) • Norfenfluramine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA); Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Metachlorophenylpiperazine (mCPP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) • Parafluorophenylpiperazine (pFPP; Fluoperazine) • Trifluoromethylphenylpiperazine (TFMPP); Quinolines: PK-7059 • Viqualine; Tryptamines: Alphaethyltryptamine (AET; Etryptamine) • Alphamethyltryptamine (AMT; Metryptamine) Enzyme Inhibitors Anabolism TPH Inhibitors AGN-2979 • Fenclonine AAAD Inhibitors Benserazide • Carbidopa Catabolism MAO Inhibitors Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima Others Precursors L-Tryptophan → 5-HTP Cofactors Ferrous Iron (Fe2+) • Magnesium (Mg2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn2+) Others Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Reuptake Enhancers: Tianeptine

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