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Encyclopedia > Sibutramine
Sibutramine chemical structure
Sibutramine
Systematic (IUPAC) name
1-(4-chlorophenyl)-N,N-
dimethyl-a-(2-methylpropyl)-
cyclobutanemethanamine
Identifiers
CAS number 106650-56-0
ATC code A08AA10
PubChem 2215
DrugBank APRD00456
Chemical data
Formula C17H26ClN
Mol. weight 279.85
Pharmacokinetic data
Bioavailability Resorption 77%, considerable first-pass metabolism
Metabolism liver
Half life sibutramine approx. 1h
metabolite 1 14h
metabolite 2 16h
Excretion sibutramine and active metabolites : mainly biliar
inactive metabolites : mainly urine
Therapeutic considerations
Pregnancy cat.

X, no human data existing, teratogenic potential in animal studies Image File history File links Sibutramine, drawn in OpenOffice. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A08A Antiobesity preparations, excluding diet products A08AA Centrally acting antiobesity products A08AA01 Phentermine A08AA02 Fenfluramine A08AA03 Amfepramone A08AA04 Dexfenfluramine A08AA05 Mazindol A08AA06 Etilamfetamine A08AA07 Cathine A08AA08 Clobenzorex A08AA09 Mefenorex A08AA10 Sibutramine A08AA56 Ephedrine, combinations A08AB Peripherally... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms anggjgjhnd cell (b). ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ...

Legal status

Schedule IV (USA) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral

Sibutramine (Meridia® in the USA, Reductil® in Europe), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally-acting stimulant chemically related to amphetamine, methamphetamine, and phentermine (one of the drugs in the Fen-Phen combination). Sibutramine is classified as a Schedule IV controlled substance in the United States. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... A stimulant is a drug that increases the activity of the sympathetic nervous system and produces a sense of euphoria or the feeling of being more awake. ... Amphetamine (alpha-methyl-phenethylamine), also known as speed, is a synthetic stimulant used to suppress the appetite, control weight, and treat disorders including narcolepsy and Attention-deficit hyperactivity disorder. ... The examples and perspective in this article or section may not represent a worldwide view. ... Phentermine is a phenethylamine primarily used as an appetite suppressant. ... Fen-phen was an anti-obesity medication (an anorectic) which consisted of two drugs: fenfluramine and phentermine. ... The Controlled Substances Act (CSA), Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970, is the legal foundation of the United States governments fight against the abuse of drugs and other substances. ... Wikipedia does not yet have an article with this exact name. ...

Contents


Pharmacokinetics

Sibutramine is well absorbed from the GI-Tract (77%), but undergoes a considerable first-pass metabolism reducing its bioavailability. The drug itself reaches its peak plasma level after 1 hour and has also a halflife of 1 hour. Sibutramine is metabolized by cytochrome-P450-isoenzyme CYP3A4 resulting in 2 active primary and secondary amines (called active metabolites 1 and 2) with halflives of 14 and 16 hours, respectively. Peak plasma concentrations of active metabolites 1 and 2 are reached after 3 to 4 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.


Pharmacological aspects

Sibutramine is a neurotransmitter reuptake inhibitor that helps enhance satiety by inhibiting the reuptake of serotonin (by 73%), norepinephrine (by 54%), and dopamine (by 16%); as such it is a satiety enhancer (i.e. it enhances satiety). Despite its actions upon the aforementioned neurotransmitters, sibutramine has never demonstrated any antidepressant properties. It was approved by the Food and Drug Administration (FDA) in November 1997[1] for the treatment of obesity. Satiety, or the feeling of fullness and disappearance of appetite after a meal, is a process mediated by the ventromedial nucleus in the hypothalamus. ... This article or section is in need of attention from an expert on the subject. ...


Sibutramine acts by increasing serotonin and noradrenaline levels in the brain. The serotonergic action, in particular, is thought to influence appetite. Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system and enterochromaffin cells in the gastrointestinal tract. ... Norepinephrine, known as noradrenaline outside the USA, is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... Comparative brain sizes In animals, the brain, or encephalon (Greek for in the head), is the control center of the central nervous system. ...


Contraindications

Sibutramine is contraindicated in:

To meet Wikipedias quality standards, this article or section may require cleanup. ... For other uses, see Anorexia nervosa (disambiguation). ... Clinical depression is a state of sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... Mania is a medical condition characterised by severely elevated mood. ... Hypersensitivity is an immune response that damages the bodys own tissues. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... An antidepressant is a medication designed to treat or alleviate the symptoms of clinical depression. ... A diagram showing the CNS: 1. ... For other forms of hypertension see hypertension (disambiguation). ... For other uses, see Stroke (disambiguation). ... Transient ischemic attacks (TIA) are caused by temporary disturbance of blood supply to a restricted area of brain and cause recurrent and brief (less than 24 hours) neurologic dysfunctions. ... Hyperthyroidism (or overactive thyroid gland) is the clinical syndrome caused by an excess of circulating free thyroxine (T4) or free triiodothyronine (T3), or both. ... This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ... Male Anatomy The prostate is an exocrine gland of the male mammalian reproductive system. ... Urinary retention is a lack of ability to urinate. ... A pheochromocytoma (also phaeochromocytoma, English spelling) is a tumor in the medulla of the adrenal glands (or, rarely, the ganglia of the sympathetic nervous system) which secretes excessive amounts of catecholamines, usually epinephrine and norepinephrine. ... Pregnant woman at 26-week gestation A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... A breastfeeding infant Breastfeeding is the process of a woman feeding an infant or young child with milk from her breasts, usually directly from the nipples. ...

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.


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). Cardiac arrhythmia is a group of conditions in which the muscle contraction of the heart is irregular or is faster or slower than normal. ... Paresthesia (paraesthesia in British English) is a sensation of tingling, pricking, or numbness of the skin with no apparent physical cause, more generally known as the feeling of pins and needles. ...


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. This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ... In medicine, melena or melaena refers to the black, tarry feces that are associated with gastrointestinal hemorrhage. ... Hematemesis or haematemesis is the vomiting of fresh red blood. ... Jaundice, also known as icterus (attributive adjective: icteric), is a yellowing of the skin, sclera (the white of the eyes) and mucous membranes caused by increased levels of bilirubin in the human body (or the body of another red blooded animal). ... A medical/clinical thermometer showing the temperature of 38. ... For the medical term see rigor (medicine) Rigour (American English: rigor) has a number of meanings in relation to intellectual life and discourse. ... In medicine, chest pain is a symptom of a number of serious conditions and is generally considered a medical emergency, unless the patient is a known angina pectoris sufferer and the symptoms are familiar (appearing at exertion and resolving at rest, known as stable angina). // Causes Cardiopulmonary Important cardiovascular and... Dyspnea (Latin dyspnoea, Greek dyspnoia from dyspnoos, short of breath) or shortness of breath (SOB) is perceived difficulty breathing or pain on breathing. ... Edema (BE: oedema, formerly known as dropsy) is swelling of any organ or tissue due to accumulation of excess fluid. ...


Currently, no case of pulmonary hypertension has been noted, although related compounds (such as Fen-Phen) have shown this rare but clinically significant problem. In medicine, pulmonary hypertension (PH) is an increase in blood pressure in the pulmonary artery or lung vasculature. ... Fen-phen was an anti-obesity medication (an anorectic) which consisted of two drugs: fenfluramine and phentermine. ...


Interactions

Sibutramine has a number of clinically significant interactions[citation needed].


Dosage

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


Safety concerns by pressure groups

Studies are ongoing into reports of sudden death, heart failure, renal failure and gastrointenstinal problems. Despite petitions[2], the drug has not been banned by the FDA, but was part of a Senate hearing in 2005[3]. Renal failure is the condition where the kidneys fail to function properly. ...


A large randomized-controlled study with over 9000 patients (SCOUT) is currently ongoing to examine whether or not sibutramine reduces the risk for cardiovascular complications in people at high risk for heart disease.


References

  1. ^ FDA 1997 approval.
  2. ^ Petition by Public Citizen to FDA to withdraw sibutramine
  3. ^ Bruce Japsen. "FDA weighs decision on Meridia ; Health advisory likely for Abbott obesity drug". Chicago Tribune. Chicago, Ill.: Mar 13, 2005. pg. 1.

Public Citizen is a U.S. non-governmental organization, founded by Ralph Nader in 1971 and based in Washington, DC. Its activities span across a diverse range of issues, including energy policy, trade policy, campaign finance reform and accountability, consumer protection, medical malpractice, and public health. ...

External links

  • Meridia (manufacturer's website)
  • RxList


Stimulants - edit

Caffeine | Nicotine | Modafinil | Adrafinil | Armodafinil A stimulant is a drug that increases the activity of the sympathetic nervous system and produces a sense of euphoria or the feeling of being more awake. ... Caffeine (sometimes called guaranine when found in guarana, mateine when found in mate, and theine when found in tea) is a xanthine alkaloid found in the leaves and beans of the coffee tree, in tea, yerba mate, guarana berries, and in small quantities in cocoa, the kola nut and the... Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco, and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. ... Modafinil (commercial trade names Provigil, Modiodal (UK, France, Mexico), Vigil (Germany), Sparlon (US), Alertec (Canada), and possibly Vigicer) is an eugeroic drug generally prescribed to treat narcolepsy, made by the pharmaceutical company Cephalon Inc. ... Adrafinil chemical structure Adrafinil is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention in elderly patients. ... Armodafinil (Nuvigil®) is a drug produced by the pharmaceutical company Cephalon, currently in the process of receiving FDA approval. ...

Sympathomimetic amines (R01, A08, and others) - edit

Benzylpiperazine | Cathinone | CFT | Chlorphentermine | Cocaine | Diethylpropion | Ephedrine | Fenfluramine | Mazindol | 4-Methyl-aminorex | Methylone | Methylphenidate | Pemoline | Phendimetrazine | Phenmetrazine | Phentermine | Phenylephrine | Propylhexedrine | Pseudoephedrine | Sibutramine | Synephrine Sympathomimetic drugs are substances that mimic the effects of the hormone adrenaline. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A08A Antiobesity preparations, excluding diet products A08AA Centrally acting antiobesity products A08AA01 Phentermine A08AA02 Fenfluramine A08AA03 Amfepramone A08AA04 Dexfenfluramine A08AA05 Mazindol A08AA06 Etilamfetamine A08AA07 Cathine A08AA08 Clobenzorex A08AA09 Mefenorex A08AA10 Sibutramine A08AA56 Ephedrine, combinations A08AB Peripherally... Benzylpiperazine (BZP) is a recreational drug with euphoric, stimulant effects. ... General Information Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... To meet Wikipedias quality standards, this article or section may require cleanup. ... This article is about the drug cocaine. ... Diethylpropion (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ... Ephedrine (EPH) is a sympathomimetic amine almost identical in structure to the synthetic derivatives amphetamine and methamphetamine. ... Fenfluramine is a drug that was part of the Fen-Phen anti-obesity (the other drug being phentermine). ... 4-Methyl-Aminorex is a stimulant drug of the 2-Amino-5-Aryloxazoline class. ... Methylone is a designer drug that is an analog of MDMA (Ecstasy). ... Methylphenidate (MPH) is an amphetamine-like prescription stimulant commonly used to treat Attention Deficit Hyperactivity Disorder (ADHD) in children and adults. ... Pemoline is a medication for Attention-deficit hyperactivity disorder (ADHD). ... Phendimetrazine (Bontril®) is a weight loss medication. ... Phenmetrazine is an amphetamine-like drug. ... Phentermine is a phenethylamine primarily used as an appetite suppressant. ... Phenylephrine or neosynephrine is an α-agonist used primarily as a decongestant, as an agent to dilate the pupil, and rarely to increase blood pressure. ... Basics: Propylhexedrine is an over-the-counter nasal decongestant found in Benzedrex nasal inhalers. ... Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. ... Synephrine Synephrine is a dietary supplement aimed at encouraging fat loss. ...

See also amphetamines

  Results from FactBites:
 
Sibutramine - Wikipedia, the free encyclopedia (586 words)
Sibutramine (Meridia® in the USA, Reductil® in Europe), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity.
Sibutramine is classified as a Schedule IV controlled substance in the United States.
Sibutramine is a neurotransmitter reuptake inhibitor that helps enhance satiety by inhibiting the reuptake of serotonin (by 73%), norepinephrine (by 54%), and dopamine (by 16%); as such it is a satiety enhancer (i.e.
  More results at FactBites »

 
 

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