Omiloxetine

Omiloxetine

Omiloxetine
Systematic (IUPAC) name
2-[(3R,4S)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-piperidinyl]-1-(4-fluorophenyl)ethanone
Clinical data
Legal status
?
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII
ChEMBL
Chemical data
Formula C27H25F2NO4 
Mol. mass 465.489 g/mol
Physical data
Density 1.3±0.1 g/cm³
Melt. point 228.65 °C (444 °F)
Boiling point 587.2 °C (1089 °F)
Solubility in water 0.0015 mg/mL (20 °C)

Omiloxetine (INN) is an antidepressant with a similar chemical structure to that of paroxetine which either was or is still under development by Ferrer Internacional for the treatment of major depression.[1] It acts as a highly selective serotonin reuptake inhibitor (SSRI), and is said to possess a greater degree of selectivity for serotonin reuptake over dopamine and norepinephrine reuptake compared to other SSRIs.[1] Though omiloxetine is listed as still under development on Ferrer's website, there has been no new news on the drug since late 2005.[2]

Mechanism of Action

Neurons communicate with one another through the release of endogenous neurotransmitters. These neurotransmitters are released into the synaptic cleft (the space between one neuron and the next) by the activated neuron, and bind to receptors present on the cellular surface of the target neuron. The binding of neurotransmitters to these receptors ultimately causes the target neuron to become activated, thus potentiating the signal from one neuron to the next.

To prevent the over-activation of neurons, neurotransmitters are removed from the synapse soon after release. This can take place either through the action of enzymatic degradation of neurotransmitters (e.g. monoamine oxidase), or through the reabsorption of neurotransmitters by the releasing neuron (e.g. monoamine transporter). Belonging to the class of drugs known as selective serotonin reuptake inhibitors (SSRIs), omiloxetine acts on the later, preventing the reuptake of serotonin from the synapse by the serotonin transporter. This causes serotonin to remain in the synapse for a longer period of time, thus improving the ability of neurons to communicate with one another. Treatment with SSRI's has shown to be beneficial in those with mood disorders such as depression and generalized anxiety disorder.[3]

Advantages

One of the primary differences between omiloxetine and other SSRIs is that the therapeutic index of omiloxetine is much wider than other SSRIs. As such, treatment with omiloxetine would reportedly be beneficial in patients that are at a higher risk of developing dose-related adverse effects secondary to SSRI treatment.[4]

Development

On January 4, 2001, Ferrer Internacional submitted a patent for a more efficient method of synthesizing an important intermediate of omiloxetine,[5] which was later published on April 19, 2005.

On December 8, 2003, Ferrer International submitted a request for "worldwide partners" for the development of omiloxetine.[1] Two years later on December 5, 2005, Ferrer International submitted a request for "licensees" to assist in the development of omiloxetine.[2]

Regulatory Synonyms

Ethanone, 2-[(3R,4S)-3[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-piperidinyl]-1-(4-fluorophenyl), rel-

Ethanone, 2-[3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-piperidinyl]-1-(4-fluorophenyl), trans-

Omiloxetine (English, French, Dutch)

Omiloxetin (German, Danish, Spanish)

Omiloxetina (Spanish, Italian)

Omiloksetiini (Finnish)

Omiloxetino (Portuguese)

References

  1. ^ a b c De Lecea, Dr Carlos (2003-12-08). "Omiloxetine - Ferrer partnering opportunity, worldwide Ferrer preclinical data". R & D Focus Drug News. Retrieved 2012-05-19. 
  2. ^ a b Terencio, Jose (2005-12-05). "Omiloxetine - Ferrer licensing offer, worldwide". R & D Focus Drug News. Retrieved 2012-05-19. 
  3. ^ Mayo Clinic Staff (2014-02-21). "Depression (major depressive disorder)". Retrieved 2014-11-26. 
  4. ^ TERENCIO ALEMANY JOSE VICENTE (2004). "PRECLINICAL CHARACTERIZATION OF OMILOXETINA, A NEW SELECTIVE INHIBITOR OF SEROTONIN RECEPTACIÓN: ANTIDEPRESSANT ACTIVITY AND SIDE EFFECTS.". Retrieved 2014-11-26. 
  5. ^ Rafael Foguet (2001-01-04). "Reacting p-fluoroacetophenone with formaldehyde and methylbenzylaminethen hydrogenation, cyclization and reducing to form chemical intermediates for paroxetine and omiloxetine". Retrieved 2014-11-26.