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Reboxetine chemical structure
Reboxetine

2-[(2-ethoxyphenoxy)-phenyl-methyl]morpholine
IUPAC name
CAS number
98769-81-4
ATC code

N06AX18

PubChem
29797
DrugBank
APRD00198
Chemical formula {{{chemical_formula}}}
Molecular weight 313.391 g/mol
Bioavailability 94.5%[1]
Metabolism Hepatic CYP3A4
Elimination half-life 13 hours[2]
Excretion Renal
Pregnancy category
Legal status Rx-only
Routes of administration 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]

Mode of action Edit

Unlike most antidepressants on the market, reboxetine is a norepinephrine reuptake inhibitor (NRI); it does not inhibit the reuptake of serotonin, therefore it can be safely combined with an SSRI.

Side effects Edit

Common side effects of reboxetine include: dry mouth, constipation, headache, drowsiness, dizziness, excessive sweating and insomnia. Hypertension has been infrequently seen.

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.

Metabolism Edit

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]

Interactions with other medications Edit

Because of its reliance on CYP3A4, reboxetine O-desethylation is markedly inhibited by papaverine and ketoconazole.[4]

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.

The sedative properties of Lorazepam can be increased because Reboxetine interferes with its excretion.

History Edit

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.

References and End Notes Edit

  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. 4.0 4.1 4.2 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 linksEdit


Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine
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