sibutramine

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A drug that suppresses appetite by inhibiting the reuptake of the neurotransmitters norepinephrine and serotonin, used in the management of obesity.

[Alteration of CY(CLO)– + BUT(YL) + perhaps (T)R(I)– (from its three methyl groups) + AMINE.]

Anorectic drug used in the treatment of obesity, trade name Reductil.

An FDA-approved prescription drug for weight loss containing a combination of serotonin and andronergics that has been shown to promote a feeling of fullness while apparently not influencing hunger; Meridia(r) is an example.

Brand names: Meridia®

Chemical formula:

Drug Forms:
• Sibutramine capsules (below)
• Sibutramine Hydrochloride Oral capsule

Español:
• Cápsulas de sibutramina
• Sibutramina Clorhidrato, Cápsula oral

Sibutramine capsules

What are sibutramine capsules?

SIBUTRAMINE (Meridia®) is used to control hunger in patients who are overweight. Sibutramine is prescribed along with a reduced-calorie diet and, if appropriate, an exercise program. Do not share this medicine with anyone else. Generic sibutramine capsules are not yet available.

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

They need to know if you have or have had any of these conditions:
• anorexia nervosa, bulimia or other eating disorder
• bleeding disorder
• depression or other mood disorder
• gallstones
• glaucoma
• heart disease, such as congestive heart failure or a previous heart attack
• heart rhythm problems or palpitations, chest pain
• high blood pressure
• kidney disease or receiving dialysis
• liver disease
• lung disease
• migraine headaches
• osteoporosis
• Parkinson's disease
• previous use of other weight loss drugs
• sleeplessness
• seizures (epilepsy or convulsions)
• stroke or symptoms of a stroke (i.e., transient ischemic attacks or TIAs)
• thyroid disease
• an unusual or allergic reaction to sibutramine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take sibutramine capsules by mouth. Follow the directions on the prescription label. Swallow with a drink of water. You may take this medicine with meals or food. Do not take your medicine more often than directed. Do not stop taking except on your prescriber's advice.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

What if I miss a dose?

What drug(s) may interact with sibutramine?

Do not take sibutramine with the following medications:
• medicines called MAO Inhibitors-phenelzine (Nardil®), tranylcypromine (Parnate®), isocarboxazid (Marplan®), selegiline (Eldepryl®)
• other medicines for weight loss, including herbal and nonprescription weight-loss drugs, like Ma huang or ephedra
• some medicines for migraines (such as dihydroergotamine, ergotamine, eletriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan)
• tryptophan

Sibutramine may also interact with:
• bosentan
• bupropion
• dextromethorphan
• fentanyl
• grapefruit juice
• ketoconazole
• linezolid
• lithium
• medicines for high blood pressure
• medicines for allergy, cold or flu symptoms (decongestants, cough suppressants)
• medicines for anxiety, depression or other mental problems
• meperidine
• procarbazine
• St. John's wort
• voriconazole

Tell your prescriber or other health care provider about all other medicines you are taking, including non-prescription medicines and 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 sibutramine?

Visit your prescriber regularly to have your blood pressure and heart rate checked. Contact your prescriber if you think you are experiencing any unusual side effects.

Keep in mind that sibutramine was intended to be used in addition to a healthy diet and appropriate exercise. The best results are achieved this way. Do not increase or in any way change your dose without consulting your prescriber.

A weight-loss of 4 pounds or more during your first month of treatment is a good indicator of success with sibutramine. Most of the weight you will lose will be lost gradually during 6—12 months. Many people who lose weight and remain on sibutramine therapy maintain their weight loss.

You should not use herbal or over-the-counter weight-loss products while taking sibutramine. Non-drug nutritional supplements, like vitamins, minerals, and proteins or amino acids (with the exception of tryptophan), can be used with sibutramine. You should make sure your prescriber knows what nutritional supplements you are taking and why you are taking them.

What side effects may I notice from taking sibutramine?

Side effects that you should report to your prescriber or health care professional as soon as possible:
Rare or uncommon:
• bleeding, easy bruising, nose bleeds, bleeding of gums
• chest pain
• difficulty breathing
• fever
• heart palpitations
• seizures
• severe dizziness
Stop using sibutramine and call your prescriber or health care professional as soon as possible if you experience any of these side effects.
More common:
• increased heart rate
• increased blood pressure
• menstrual problems
• muscle or joint pain
• pain, burning or tingling in the hands or feet
• unusual swelling of the arms or legs
• unusual tiredness or weakness
• visual problems

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 irritability
• anxiety
• back pain
• constipation
• diarrhea
• difficulty sleeping
• dizziness
• drowsiness
• dry mouth
• gas
• headache
• nausea or vomiting
• skin problems
• stomach problems
• sweating
• taste disturbance
• throat irritation or pain

Where can I keep my medicine?

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

Store at controlled room temperature 15—30 degrees C (59—86 degrees F). Keep container tightly closed. Protect capsules from heat, light and moisture. 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.

Sibutramine
Systematic (IUPAC) name
1-[1-(4- chlorophenyl) cyclobutyl]- N,N,3- trimethylbutan- 1-amine
Identifiers
CAS number	106650-56-0
ATC code	A08AA10
PubChem	5210
DrugBank	APRD00456
ChemSpider	5021
Chemical data
Formula	C17H26ClN
Mol. mass	279.85 g/mol
Pharmacokinetic data
Bioavailability	Absorption 77%, considerable first-pass metabolism
Metabolism	Hepatic (CYP3A4-mediated)
Half life	sibutramine approx. 1 hour Metabolite 1: 14 hours Metabolite 2: 16 hours
Excretion	Biliary (sibutramine and active metabolites), renal (inactive metabolites)
Therapeutic considerations
Pregnancy cat.	C(AU) C(US) No human data exists; inconclusive evidence of teratogenic potential in animal studies
Legal status	Schedule IV(US)
Routes	Oral

Sibutramine (trade name Meridia in the U.S. and Canada, Ectiva in South Africa, Reductil in Europe and most other countries), usually as sibutramine hydrochloride monohydrate, is an orally administered agent for the treatment of obesity, as an appetite suppressant. It is a centrally-acting serotonin-norepinephrine reuptake inhibitor structurally related to amphetamines,^[1] although its mechanism of action is distinct.^[2]

Sibutramine is manufactured by Abbott Laboratories. It is classified as a Schedule IV controlled substance in the United States, despite having virtually no potential for abuse (due to its lack of appreciable dopaminergic effects). It is likely that the compound's use as an anorectic is the sole reason is it classified as a controlled drug, as "overprescription" of anorectics (as a class) in the mid-20th century resulted in a number of cases of abuse or addiction.

Contents 1 Pharmacokinetics 2 Pharmacodynamics 3 Contraindications 4 Side effects 5 Interactions 6 Dosage 7 Safety concerns 8 References 9 External links

Pharmacokinetics

Sibutramine is well absorbed from the GI tract (77%), but undergoes considerable first-pass metabolism, reducing its bioavailability. The drug itself reaches its peak plasma level after 1 hour and has also a half-life of 1 hour. Sibutramine is metabolized by cytochrome P450 isozyme CYP3A4 into two pharmacologically-active primary and secondary amines (called active metabolites 1 and 2) with half-lives of 14 and 16 hours, respectively. Peak plasma concentrations of active metabolites 1 and 2 are reached after three to four hours. The following metabolic pathway mainly results in two inactive conjugated and hydroxylated metabolites (called metabolites 5 and 6). Metabolites 5 and 6 are mainly excreted in the urine.

Pharmacodynamics

Sibutramine is a neurotransmitter reuptake inhibitor that reduces the reuptake of serotonin (by 53%), norepinephrine (by 54%), and dopamine (by 16%), thereby increasing the levels of these substances in synaptic clefts and helping enhance satiety; the serotonergic action, in particular, is thought to influence appetite. Older anorectic agents such as amphetamine and fenfluramine force the release of these neurotransmitters rather than affecting their reuptake.^[2]

Despite having a mechanism of action similar to tricyclic antidepressants, sibutramine has failed to demonstrate antidepressant properties in animal studies. It was approved by the U.S. Food and Drug Administration (FDA) in November 1997^[3] for the treatment of obesity.

Contraindications

Sibutramine is contraindicated in:

• Psychiatric conditions as bulimia nervosa, anorexia nervosa, serious depression or preexisting mania
• Patients with a history of or a predisposition to drug or alcohol abuse
• Hypersensitivity to the drug
• Patients below 18 years of age
• Concomitant treatment with a MAO inhibitor, antidepressant or other centrally active drugs, particularly other anoretics
• Hypertension that is not sufficiently controlled (caution in controlled hypertension)
• Existing pulmonary hypertension
• Existing damage on heart valves, coronary heart disease, congestive heart failure, serious arrhythmias, previous myocardial infarction
• Stroke or transient ischemic attack (TIA)
• Hyperthyroidism (overactive thyroid gland)
• Closed angle glaucoma
• Seizure disorders
• Enlargement of the prostate gland with urinary retention (relative C.I.)
• Pheochromocytoma
• Pregnant and lactating women (relative C.I.)

Side effects

Frequently encountered side effects are: dry mouth, paradoxically increased appetite, nausea, strange taste in the mouth, upset stomach, constipation, trouble sleeping, dizziness, drowsiness, menstrual cramps/pain, headache, flushing, or joint/muscle pain.

Sibutramine can substantially increase blood pressure and pulse in some patients. Therefore all patients treated with sibutramine should have regular monitoring of blood pressure and pulse.

The following side effects are infrequent but serious and require immediate medical attention: cardiac arrhythmias, paresthesia, mental/mood changes (e.g., excitement, restlessness, confusion, depression, rare thoughts of suicide).

Symptoms that require urgent medical attention are seizures, problems urinating, abnormal bruising or bleeding, melena, hematemesis, jaundice, fever and rigors, chest pain, hemiplegia, abnormal vision, dyspnea and edema.

Currently, no case of pulmonary hypertension has been noted, although related compounds (such as Fen-Phen) have shown this rare but clinically significant problem.

Interactions

Sibutramine has a number of clinically significant interactions. The concomitant use of sibutramine and monoamine oxidase inhibitors (MAOIs, such as selegiline) is not indicated, as it may increase the risk of serotonin syndrome, a somewhat rare but serious adverse drug reaction.^[4] Sibutramine should not be taken within two weeks of stopping or starting an MAOI. Taking both sibutramine and certain medications used in the treatment of migraines—such as ergolines and triptans—, as well as opioids, may also increase the risk for serotonin syndrome, as may the use of more than one serotonin reuptake inhibitor at the same time.^[4]

The concomitant use of sibutramine and drugs which inhibit CYP3A4, such as ketoconazole and erythromycin, may increase plasma levels of sibutramine.^[5] Sibutramine does not affect the efficacy of hormonal contraception.^[4]

Dosage

10 mg once daily (usually in the morning), if this proves insufficient the dose may be increased to 15 mg daily after 4 weeks.

Safety concerns

Studies are ongoing into reports of sudden death, heart failure, renal failure and gastrointestinal problems. Despite a petition by Ralph Nader-founded NGO Public Citizen,^[6] the FDA made no attempts to withdraw the drug, but was part of a Senate hearing in 2005.^[7] Similarly, Dr. David Graham, FDA "whistleblower", testified before a Senate Finance Committee hearing that sibutramine may be more dangerous than the conditions it is used for.^[8]

A large randomized-controlled study with 10,742 patients (SCOUT) examined whether or not sibutramine administered within a weight management program reduces the risk for cardiovascular complications in people at high risk for heart disease and concluded that "Six-week treatment with sibutramine appears to be efficacious, tolerable and safe in this high-risk population for whom sibutramine is usually contraindicated."^[9]

On December 22, 2008, the Food and Drug Administration issued an alert to consumers naming 27 different products marketed as “dietary supplements” for weight loss, that illegally contain undisclosed amounts of sibutramine.^[10][11] In March 2009, Dieter Müller et al. published a study of sibutramine poisoning cases from similar Chinese "herbal supplements" sold in Europe, containing as much as twice the dosage of the legally licensed drug.^[12]

An additional 34 products were recalled by the FDA on April 22, 2009, further underscoring the risks associated with unregulated "herbal supplements" to unsuspecting persons. This concern is especially relevant to those with underlying medical conditions incompatible with undeclared pharmaceutical adulterants.^[13]

References

1. ^ "New Drugs". Australian Prescriber 25 (1): 22. 2002.  PDF
2. ^ ^{a b} Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC (1998). "Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine". Int J Obes Relat Metab Disord 22 Suppl 1: S18–28; discussion S29. PMID 9758240. 
3. ^ U.S. Food and Drug Administration (November 24, 1997). FDA APPROVES SIBUTRAMINE TO TREAT OBESITY. Press release. http://www.fda.gov/bbs/topics/ANSWERS/ANS00835.html. Retrieved on 2007-04-29. 
4. ^ ^{a b c} "Meridia Side Effects, and Drug Interactions". RxList.com. 2007. http://www.rxlist.com/cgi/generic/sibutramine_ad.htm. Retrieved on 2007-04-29. 
5. ^ (Portuguese) Cloridrato de sibutramina monoidratado. Bula. [Sibutramine hydrochloride monohydrate—label information]. Medley (2007).
6. ^ Wolfe, Sidney M.; Larry D. Sasich, Elizabeth Barbehenn (March 19, 2002). "Petition to FDA to ban the diet drug sibutramine (MERIDIA) (HRG Publication #1613)". Public Citizen. http://www.citizen.org/publications/print_release.cfm?ID=7160. Retrieved on 2007-04-29. 
7. ^ Bruce Japsen (13 March 2005). "FDA weighs decision on Meridia ; Health advisory likely for Abbott obesity drug". Chicago Tribune. Chicago, Illinois. pp. 1. 
8. ^ Hearing of 17 November 2004. Related CBS news item 19 November 2004.
9. ^ Torp-Pedersen C, Caterson I, Coutinho W, et al. (2007). "Cardiovascular responses to weight management and sibutramine in high-risk subjects: an analysis from the SCOUT trial". Eur. Heart J. 28 (23): 2915–23. doi:10.1093/eurheartj/ehm217. PMID 17595194. http://eurheartj.oxfordjournals.org/cgi/content/full/28/23/2915. 
10. ^ U.S. Food and Drug Administration (22 December 2008). FDA warns consumers about tainted weight loss pills. Press release. http://www.fda.gov/bbs/topics/NEWS/2008/NEW01933.html. 
11. ^ "Consumer directed questions and answers about FDA’s initiative against contaminated weight loss products". U.S. Food and Drug Administration Center for Drug Evaluation and Research. 22 December 2008. http://www.fda.gov/cder/consumerinfo/weight_loss_products.htm. 
12. ^ Müller D, Weinmann W, Hermanns-Clausen M (2009). "Chinese slimming capsules containing sibutramine over the internet—a case series". Dtsch Arztebl Int 106 (13): 218–22. doi:10.3238/arztebl.2009.0218. 
13. ^ WebMD April 22nd 2009 publication of FDA recall information. [1] 22 April 2009.

External links

• Sibutramine drug information from Lexi-Comp. Includes dosage information and a comprehensive list of international brand names
• Meridia (Manufacturer's website)

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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: Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: Cinanserin • Deramciclane • Dimebolin • Dotarizine • Eltoprazine • FR-260,010 • Ketanserin • 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: 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: BRL-46,470 • ICS-205,930 • Lu AA21004 • MDL-72,222 • Memantine 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 • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Litoxetine • Lubazodone • Paroxetine • 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 • NS2359 • SEP-225289 • SEP-227162 • Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Tropanes: Cocaine; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine/Pyrilamine • Pheniramine • Tripelennamine; Opioids: Meperidine/Pethidine • Methadone • Propoxyphene • Tramadol; Others: Cyclobenzaprine • Dextromethorphan • Mesembrine • SB-649915 • Sibutramine • Ziprasidone TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing Agents Aminoindanes: ETAI • MDAI • MDMAI • MMAI • TAI; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Benzofurans: 5-APDB; Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: 2-Methyl-MDA • 3-Methoxy-4-methylamphetamine • 4-Bromomethcathinone • 4-Fluoroamphetamine • 4-Fluoromethamphetamine • 4-Methylamphetamine • 4-Methylmethamphetamine • 4-Methylthioamphetamine • 5-Methyl-MDA • BDB • BOH • Butylone • Chlorphentermine • Diethylcathinone • Dimethylcathinone • EBDB • Ethylone • Fenfluramine • Flephedrone • MBDB • MDA • MDEA • MDMA (Ecstasy) • MDOH • MDPEA • Mephedrone • Methylone • MMDA • MMDMA • Norfenfluramine • para-Bromoamphetamine • para-Chloroamphetamine • para-Chloromethamphetamine • para-Iodoamphetamine • para-Methoxyamphetamine • para-Methoxyethylamphetamine • para-Methoxymethamphetamine; Quinolines: PK 7059 • Viqualine; Tryptamines: α-ET • α-MT 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 Iron • Tetrahydrobiopterin • Vitamin B3 (Niacin/Nicotinamide/NADPH) • Vitamin B6 (Pyridoxine/Pyridoxamine/Pyridoxal 5-Phosphate) • Vitamin B9 (Folic Acid/Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc Others Activity Enhancers: BPAP • PPAP; Reuptake Enhancers: Tianeptine

v • d • e Dopaminergics Receptor Ligands Agonists Benzazepines: Fenoldopam • SKF 38393 • SKF 82958; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: A-86929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxathrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazines: Aripiprazole • Piribedil • WAY-100,635; Others: A-412,997 • Aplindore • Memantine • Pramipexole • Pukateine • Quinpirole • RDS-127 • Ropinirole • Rotigotine Antagonists Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH 23390 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine Reuptake Inhibitors Plasmalemmal DAT Inhibitors Piperazines: DBL-583 • GBR-12935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • HDMP-28 • Methylphenidate • Phencyclidine • Pipradrol; Pyrovalerones: MDPV • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane • Lometopane • RTI-121 • RTI-126 • RTI-150 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benztropine • Bromantane • BTQ • BTS 74,398 • Bupropion • Cypenamine • Diclofensine • Dimethocaine • Diphenylprolinol • Dizocilpine • DOV 102,677 • DOV 21,947 • DOV 216,303 • Ethcathinone • Fencamfamine • GYKI-52895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Nisoxetine • Nomifensine • NS2359 • O-2172 • Prolintane • Radafaxine • SEP-225289 • SEP-227162 • Sibutramine • Tametraline • Tripelennamine TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing Agents Alkylamines: Cyclopentamine • Propylhexedrine; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Oxazolines: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamines: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • Lisdexamfetamine • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Propylamphetamine • Tyramine • Xylopropamine; Piperazines: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine Enzyme Inhibitors Anabolism PAH Inhibitors 3,4-Dihydroxystyrene TH Inhibitors 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone 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; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline COMT Inhibitors Entacapone • Tolcapone DBH Inhibitors Disulfiram • Nepicastat • Tropolone Others Precursors L-Phenylalanine • L-Tyrosine • L-DOPA Cofactors Iron • Tetrahydrobiopterin • Vitamin B3 (Niacin/Nicotinamide/NADPH) • Vitamin B6 (Pyridoxine/Pyridoxamine/Pyridoxal 5-Phosphate) • Vitamin B9 (Folic Acid/Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc Others Activity Enhancers: BPAP • PPAP; Others: Amantadine • Memantine • Rimantadine

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