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Encyclopedia > Reboxetine
Reboxetine
Systematic (IUPAC) name
2-[(2-ethoxyphenoxy)-phenyl-methyl]morpholine
Identifiers
CAS number 98769-81-4
ATC code N06AX18
PubChem 29797
DrugBank APRD00198
Chemical data
Formula C19H23NO3 
Mol. mass 313.391 g/mol
Pharmacokinetic data
Bioavailability 94.5%[1]
Protein binding 98%
Metabolism Hepatic CYP3A4
Half life 13 hours[2]
Excretion Renal
Therapeutic considerations
Pregnancy cat.

? Image File history File links Reboxetine. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass (abbreviated MM) of a substance, formerly also 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. ... Many drugs are bound to Blood plasma proteins. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... 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 during pregnancy. ...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral

Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesilate (i.e. methanesulfonate) salt is sold under tradenames including Edronax®, Norebox®, Prolift®, Solvex® or Vestra®. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine.[3] 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 recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a medication taken to alleviate clinical depression or dysthymia (milder depression). ... Clinical depression (also called major depressive disorder, or sometimes unipolar when compared with bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... Panic disorder is a diagnosed psychiatric mental condition that causes the sufferer to experience sporadic, intense, and often reoccurring panic attacks. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... A trade name, also known as a trading name or a business name, is the legal name of a business, or the name which a business trades under for commercial purposes. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

Contents

Mode of action

Unlike most antidepressants on the market, reboxetine is a norepinephrine reuptake inhibitor (NERI); it does not inhibit the reuptake of serotonin, therefore it can be safely combined with an SSRI. Norepinephrine reuptake inhibitors (NRIs) are compounds that increase amounts of the neurotransmitter norepinephrine in the brain by inhibiting its reuptake at synapses. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ... Selective serotonin reuptake inhibitors (SSRIs) are a class of antidepressants used in the treatment of depression, anxiety disorders and some personality disorders. ...


Side effects

Common side effects of reboxetine include: dry mouth, constipation, headache, drowsiness, dizziness, excessive sweating and insomnia. Hypertension has been infrequently seen. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to eliminate; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Insomnia is characterized by an inability to sleep and/or inability to remain asleep for a reasonable period. ...


In 4 to 8% of all patients treated the medication has to be discontinued due to following reasons (percentages represent mean values):

  • insomnia 1.3%
  • excessive sweating 1.1%
  • vertigo/hypotension and paraesthesia 0.8%
  • dizziness, impotence, and other urological problems 0.5% each

Some other rare side effects include anxiety, loss of appetite, urinary retention in men, pain on ejaculation, increased orgasm intensity, and premature/quickened ejaculation.


Reboxetine is very well tolerated. So far no attributable fatalities have been noted. However, it is known to induce a massive mania in those with bipolar disorder. For other uses, see Bipolar. ...


Metabolism

Both the (R,R)-(-) and (S,S)-(+)-enantiomers of reboxetine are predominantly metabolized by the CYP3A4 isoenzyme.[4] The primary metabolite of reboxetine is O-desethylreboxetine, and there are also three minor metabolites—Phenol A, Phenol B, and UK1, Phenol B being the most minor.[4] Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... Isozymes, (or isoenzymes) are isoforms (closely related variants) of enzymes. ...


Interactions with other medications

Because of its reliance on CYP3A4, reboxetine O-desethylation is markedly inhibited by papaverine and ketoconazole.[4] Papaverine is an opium alkaloid (opiate) used intravenously in the treatment of erectile dysfunction. ... Nizoral® logo Ketoconazole is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. Due to its side-effect profile, it has been superseded by newer antifungals, such as fluconazole and itraconazole. ...


According to Weiss et al, reboxetine is an intermediate-level inhibitor of P-glycoprotein, which gives it the potential to interact with ciclosporin, tacrolimus, paroxetine, sertraline, quinidine, fluoxetine, fluvoxamine.[5] It has also been known to interact with the analgesic codeine. P-glycoproteins are a type of protein that appear to have developed as a mechanism to protect the body from harmful substances by acting as efflux transporters. ... Ciclosporin (INN), cyclosporine or cyclosporin (former BAN), is an immunosuppressant drug. ... Tacrolimus (also FK-506 or Fujimycin) is a 23-membered macrolide lactone discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. ... Paroxetine or paroxetine hydrochloride is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Sertraline hydrochloride (also labeled under numerous brand names: Zoloft, Sertralin, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is a popular orally administered antidepressant of the selective serotonin reuptake inhibitor (SSRI) type. ... Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ... Fluoxetine hydrochloride is an antidepressant drug used medically in the treatment of depression, body dysmorphic disorder, obsessive-compulsive disorder, bulimia nervosa, premenstrual dysphoric disorder, hypochondriasis and panic disorder. ... Fluvoxamine (brand name as Luvox®, Faverin®, Fevarin® and Dumyrox®) is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ...


The sedative properties of Lorazepam can be increased because Reboxetine interferes with its excretion. Lorazepam (marketed under the brand names Ativan®, Temesta®, Tavor®) is a drug which is a benzodiazepine derivative. ...


History

By mid-2001, reboxetine was licensed worldwide in over 50 countries, including Italy, Germany and the United Kingdom. In May 2001, however, the Food and Drug Administration declined Pharmacia's license application for the American market. As such it is yet to be available in the United States. The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and...


References and End Notes

  1. ^ Fleishaker JC (2000). "Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression". Clinical Pharmacokinetics 39 (6): 413-27. PMID 11192474.  Fulltext options
  2. ^ Edwards DM, Pellizzoni C, Breuel HP, Berardi A, Castelli MG, Frigerio E, Poggesi I, Rocchetti M, Dubini A, Strolin Benedetti M (1995). "Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding". Biopharmaceutics & Drug Disposition 16 (6): 443-60. PMID 7579027.  List of Library Holdings
  3. ^ Melloni P, Della Torre A, Lazzari E, Mazzini G and Meroni M (1985). "Configuration studies on 2-[alpha -(2-ethoxyphenoxy)benzyl]-morpholine FCE 20124". Tetrahedron 41 (1): 1393-1399.  Not available online.
  4. ^ a b c Wienkers LC, Allievi C, Hauer MJ, Wynalda MA. (1999). "Cytochrome P-450-Mediated Metabolism of the Individual Enantiomers of the Antidepressant Agent Reboxetine in Human Liver Microsomes". Drug Metabolism & Disposition 27 (11): 1334-1340. PMID 10534319.  Fulltext options
  5. ^ Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE (2003). "Inhibition of P-glycoprotein by newer antidepressants". Journal of Pharmacology & Experimental Therapeutics 305 (1): 197-204. PMID 12649369.  Fulltext options

External links

  • Reboxetine: A Novel Antidepressant

  Results from FactBites:
 
Reboxetine - Wikipedia, the free encyclopedia (488 words)
Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD.
Both the (R,R)-(-) and (S,S)-(+)-enantiomers of reboxetine are predominantly metabolized by the CYP3A4 isoenzyme.
According to Weiss et al, reboxetine is an intermediate-level inhibitor of P-glycoprotein, which gives it the potential to interact with ciclosporin, tacrolimus, paroxetine, sertraline, quinidine, fluoxetine, fluvoxamine.
Anxiety Zone - Reboxetine (209 words)
Reboxetine is currently marketed by Pharmacia and Upjohn.
By mid-2001, reboxetine was licensed worldwide in over 50 countries, including Italy, Germany and the UK.
Reboxetine has a relatively short elimination half life of 12.5 hours and therefore is often given twice daily.
  More results at FactBites »

 
 

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