S33005 is a
serotonin–norepinephrine reuptake inhibitor (SNRI) that was under
development by
Servier for the treatment of depression and related disorders. It is structurally related to
venlafaxine
Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic di ...
but has a more complex molecular structure. Venlafaxine appears to be a sigma modulator, but it is not known if S33005 shares this activity.
Synthesis
"The 1-cyano-benzocyclobutenes used as starting material are obtained, for example, by subjecting a β-
rthohalogeno-phenyl propionitrile to
intramolecular condensation
Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor ...
in the presence of
potassium amide, or by brominating a
benzocyclobutene
Benzocyclobutene (BCB) is a benzene ring fused to a cyclobutane ring. It has chemical formula .
BCB is frequently used to create photosensitive polymers. BCB-based polymer dielectrics may be spun on or applied to various substrates for use in ...
in position 1 with
''N''-bromosuccinimide, followed by exchange of the bromine atom for a cyano group by means of
sodium cyanide
Sodium cyanide is a poisonous compound with the formula Na C N. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its h ...
."
See also
*
Milnacipran
Milnacipran (trade names Ixel, Savella, Dalcipran, Toledomin) is a serotonin–norepinephrine reuptake inhibitor (SNRI) used in the clinical treatment of fibromyalgia. It is not approved for the clinical treatment of major depressive disorder in ...
References
External links
PubMed searchBinding Database* The patent and synthesis discussion can be found in
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Pharmacodynamics
Pharmacodynamics (PD) is the study of the biochemical and physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of organisms ( ...
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{{Monoamine reuptake inhibitors
{{Sigma receptor modulators
Tertiary alcohols
Antidepressants
Benzocyclobutenes
Phenol ethers
Serotonin–norepinephrine reuptake inhibitors
Sigma agonists