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Gabapentinoids: Difference between revisions
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[[File:GABA.svg|250px|thumbnail|Skeletal structure of the [[GABA|gamma-aminobutyric acid]] (GABA) molecule.]] | |||
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'''Gabapentinoids''', also known as α<sub>2</sub>δ ligands, are a relatively small chemical class of [[psychoactive substances]] derived from [[GABA|gamma-aminobutyric acid]] (GABA).{{citation needed}} Members of this class include [[gabapentin]], [[F-phenibut]], [[phenibut]] and [[pregabalin]]. | '''Gabapentinoids''', also known as α<sub>2</sub>δ ligands, are a relatively small chemical class of [[psychoactive substances]] derived from [[GABA|gamma-aminobutyric acid]] (GABA).{{citation needed}} Members of this class include [[gabapentin]], [[F-phenibut]], [[phenibut]] and [[pregabalin]]. | ||
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Gabapentinoids closely resemble the α-amino acids <small>L</small>-leucine and <small>L</small>-isoleucine, and this may be of greater relevance in relation to their pharmacodynamics than their structural similarity to GABA.<ref name=":0">{{cite journal | vauthors=((Dooley, D. J.)), ((Taylor, C. P.)), ((Donevan, S.)), ((Feltner, D.)) | journal=Trends in Pharmacological Sciences | title=Ca2+ channel α2δ ligands: novel modulators of neurotransmission | volume=28 | issue=2 | pages=75–82 | date= February 2007 | url=https://linkinghub.elsevier.com/retrieve/pii/S0165614706002896 | issn=01656147 | doi=10.1016/j.tips.2006.12.006}}</ref> | Gabapentinoids closely resemble the α-amino acids <small>L</small>-leucine and <small>L</small>-isoleucine, and this may be of greater relevance in relation to their pharmacodynamics than their structural similarity to GABA.<ref name=":0">{{cite journal | vauthors=((Dooley, D. J.)), ((Taylor, C. P.)), ((Donevan, S.)), ((Feltner, D.)) | journal=Trends in Pharmacological Sciences | title=Ca2+ channel α2δ ligands: novel modulators of neurotransmission | volume=28 | issue=2 | pages=75–82 | date= February 2007 | url=https://linkinghub.elsevier.com/retrieve/pii/S0165614706002896 | issn=01656147 | doi=10.1016/j.tips.2006.12.006}}</ref> | ||
==List of Gabapentinoids== | |||
{| class="wikitable" | |||
|- | |||
! scope="col" |'''Compound''' | |||
! scope="col" style="width: 50px;" |'''R<sub>3</sub>''' | |||
! scope="col" |'''Structure''' | |||
|- | |||
|[[GABA]]||H||[[File:GABA.svg|200px]] | |||
|- | |||
|[[Pregabalin]]||CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>||[[File:Pregabalin.svg|200px]] | |||
|- | |||
|[[Gabapentin]]||C<sub>5</sub>H<sub>10</sub>||[[File:Gabapentin.svg|200px]] | |||
|- | |||
|[[Phenibut]]||C<sub>6</sub>H<sub>5</sub>||[[File:Phenibut.svg|200px]] | |||
|- | |||
|[[F-Phenibut]]||C<sub>6</sub>H<sub>4</sub>F||[[File:F-Phenibut.svg|200px]] | |||
|- | |||
|[[Baclofen]]||C<sub>6</sub>H<sub>4</sub>Cl||[[File:Baclofen.svg|200px]] | |||
|} | |||
==Pharmacology== | ==Pharmacology== | ||
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Gabapentin, pregabalin, and phenibut all undergo little or no metabolism. Conversely, gabapentin enacarbil, which acts as a prodrug of gabapentin, must undergo enzymatic hydrolysis to become active. This is done via non-specific esterases in the intestines and to a lesser extent in the liver.<ref name=":1" /> | Gabapentin, pregabalin, and phenibut all undergo little or no metabolism. Conversely, gabapentin enacarbil, which acts as a prodrug of gabapentin, must undergo enzymatic hydrolysis to become active. This is done via non-specific esterases in the intestines and to a lesser extent in the liver.<ref name=":1" /> | ||
==See also== | ==See also== | ||
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==References== | ==References== | ||
[[Category:Chemical class]] | [[Category:Chemical class]] | ||
[[Category:Pharmacology]] | [[Category:Pharmacology]] | ||
<references /> | <references /> | ||