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It is a [[GABA]] antagonist, apparently by mimicking GABA, which is it resembles.<ref name=OrgChem2007/> Homotaurine has shown activity in animal models of alcoholism, and [[acamprosate]], the N-acetyl derivative of homotaurine, was approved by the FDA in 2004 to treat alcohol dependence.<ref name=OrgChem2007>Daniel Lednicer, The Organic Chemistry of Drug Synthesis. John Wiley & Sons, 2007 ISBN 9780470180662. [https://books.google.com/books?id=N6OAhuiHqiIC&pg=PA15 Page 15]</ref>
It is a [[GABA]] antagonist, apparently by mimicking GABA, which is it resembles.<ref name=OrgChem2007/> Homotaurine has shown activity in animal models of alcoholism, and [[acamprosate]], the N-acetyl derivative of homotaurine, was approved by the FDA in 2004 to treat alcohol dependence.<ref name=OrgChem2007>Daniel Lednicer, The Organic Chemistry of Drug Synthesis. John Wiley & Sons, 2007 ISBN 9780470180662. [https://books.google.com/books?id=N6OAhuiHqiIC&pg=PA15 Page 15]</ref>


Evidence says that Homotaurine is a [[GABAA receptor|GABA<sub>A</sub>]] partial agonist <ref>{{cite journal|title=Modulation of GABA-A receptors of astrocytes and STC-1 cells by taurine structural analogs.|pmid=25119985|author=Reyes-Haro D1, Cabrera-Ruíz E, Estrada-Mondragón A, Miledi R, Martínez-Torres A.}}</ref> and a [[GABAB receptor|GABA<sub>B</sub>]] receptor partial agonist with low efficacy, becoming an antagonist and displacing full agonist as [[Gamma-Aminobutyric acid|GABA]] or [[baclofen]] <ref>{{cite journal|title=Homotaurine: a GABAB antagonist in guinea-pig ileum.|pmid=6652358|author=Giotti A, Luzzi S, Spagnesi S, Zilletti L.}}</ref>. In one study, Homotaurine reversed the catatonia induced by [[baclofen]] in rats <ref>{{cite journal|title=Baclofen induces catatonia in rats.|pmid=2823166|author=Mehta AK1, Ticku MK.}}</ref> . Homotaurine produces analgesia via [[GABAB receptor|GABA<sub>B</sub>]] receptor, effect that is abolished when applied CGP 35348, a [[GABAB receptor|GABA<sub>B</sub>]] receptor antagonist <ref>{{cite journal|title=GABA(B) receptors and opioid mechanisms involved in homotaurine-induced analgesia.|pmid=9510095|author=Serrano MI1, Serrano JS, Fernández A, Asadi I, Serrano-Martino MC.}}</ref><ref>{{cite journal|title=Role of K+ -channels in homotaurine-induced analgesia.|pmid=11468027|author=Serrano MI1, Serrano JS, Asadi I, Fernández A, Serrano-Martino MC.}}</ref> .
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Moreover, Homotaurine suppress ethanol-stimulated dopamine release, ethanol intake and preference in rats similar to [[acamprosate]] (Acetylated homotaurine analogue) <ref>{{cite journal|title=Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release.|pmid=11864639|author=Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW.}}</ref><ref>{{cite journal|title=Acamprosate reduces ethanol drinking behaviors and alters the metabolite profile in mice lacking ENT1.|pmid=21172405|author=Berton F, et al. Alcohol Clin Exp Res. 1998. .}}</ref>. [[Acamprosate]], enhance NMDA currents and inhibited [[GABAB receptor|GABA<sub>B</sub>]] receptor too. <ref>{{cite journal|title=Acamprosate enhances N-methyl-D-apartate receptor-mediated neurotransmission but inhibits presynaptic GABA(B) receptors in nucleus accumbens neurons.|pmid=9514305|author=Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW.}}</ref>{{multiple image
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Revision as of 20:01, 10 March 2016

Homotaurine[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
3-Aminopropane-1-sulfonic acid
Other names
Tramiprosate; Alzhemed; 3-APS
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.889 Edit this at Wikidata
KEGG
  • InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7) checkY
    Key: SNKZJIOFVMKAOJ-UHFFFAOYSA-N checkY
  • InChI=1/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)
    Key: SNKZJIOFVMKAOJ-UHFFFAOYAT
  • O=S(=O)(O)CCCN
Properties
C3H9NO3S
Molar mass 139.17 g·mol−1
Melting point 293 °C (559 °F; 566 K) (decomposition)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Homotaurine (3-amino-1-propanesulfonic acid (3-APS) or tramiprosate (INN)) is a synthetic organic compound. It is analogous to taurine, but with an extra carbon in its chain. Because of its similarity in structure to the neurotransmitter gamma-aminobutyric acid (GABA), it has GABAergic effects and may be useful as an anticonvulsant.[2]

Homotaurine was investigated in a Phase III clinical trial as a potential treatment for Alzheimer's disease that did not show efficacy in its primary endpoints.[3] In preclinical studies it had been found to bind to soluble amyloid beta and inhibit the formation of neurotoxic aggregates.[3][4][5]

It is a GABA antagonist, apparently by mimicking GABA, which is it resembles.[6] Homotaurine has shown activity in animal models of alcoholism, and acamprosate, the N-acetyl derivative of homotaurine, was approved by the FDA in 2004 to treat alcohol dependence.[6]

Evidence says that Homotaurine is a GABAA partial agonist [7] and a GABAB receptor partial agonist with low efficacy, becoming an antagonist and displacing full agonist as GABA or baclofen [8]. In one study, Homotaurine reversed the catatonia induced by baclofen in rats [9] . Homotaurine produces analgesia via GABAB receptor, effect that is abolished when applied CGP 35348, a GABAB receptor antagonist [10][11] .

Moreover, Homotaurine suppress ethanol-stimulated dopamine release, ethanol intake and preference in rats similar to acamprosate (Acetylated homotaurine analogue) [12][13]. Acamprosate, enhance NMDA currents and inhibited GABAB receptor too. [14]

Skeletal formula
Ball-and-stick model
The zwitterionic form of homotaurine


References

  1. ^ Homotaurine at Sigma-Aldrich
  2. ^ Fariello RG, Golden GT, Pisa M; Golden; Pisa (1982). "Homotaurine (3 aminopropanesulfonic acid; 3APS) protects from the convulsant and cytotoxic effect of systemically administered kainic acid". Neurology. 32 (3): 241–5. doi:10.1212/wnl.32.3.241. PMID 7199633.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ a b Caltagirone C et al. The potential protective effect of tramiprosate (homotaurine) against Alzheimer's disease: a review. Aging Clin Exp Res. 2012 Dec;24(6):580-7. PMID 22961121
  4. ^ Herrmann N et al. Current and emerging drug treatment options for Alzheimer's disease: a systematic review. Drugs. 2011 Oct 22;71(15):2031-65. Review. PMID 21985169
  5. ^ Aisen PS Alzhemed: a potential treatment for Alzheimer's disease. Curr Alzheimer Res. 2007 Sep;4(4):473-8. PMID 17908052
  6. ^ a b Daniel Lednicer, The Organic Chemistry of Drug Synthesis. John Wiley & Sons, 2007 ISBN 9780470180662. Page 15
  7. ^ Reyes-Haro D1, Cabrera-Ruíz E, Estrada-Mondragón A, Miledi R, Martínez-Torres A. "Modulation of GABA-A receptors of astrocytes and STC-1 cells by taurine structural analogs". PMID 25119985. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  8. ^ Giotti A, Luzzi S, Spagnesi S, Zilletti L. "Homotaurine: a GABAB antagonist in guinea-pig ileum". PMID 6652358. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
  9. ^ Mehta AK1, Ticku MK. "Baclofen induces catatonia in rats". PMID 2823166. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: numeric names: authors list (link)
  10. ^ Serrano MI1, Serrano JS, Fernández A, Asadi I, Serrano-Martino MC. "GABA(B) receptors and opioid mechanisms involved in homotaurine-induced analgesia". PMID 9510095. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  11. ^ Serrano MI1, Serrano JS, Asadi I, Fernández A, Serrano-Martino MC. "Role of K+ -channels in homotaurine-induced analgesia". PMID 11468027. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  12. ^ Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW. "Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release". PMID 11864639. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
  13. ^ Berton F, et al. Alcohol Clin Exp Res. 1998. . "Acamprosate reduces ethanol drinking behaviors and alters the metabolite profile in mice lacking ENT1". PMID 21172405. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: numeric names: authors list (link)
  14. ^ Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW. "Acamprosate enhances N-methyl-D-apartate receptor-mediated neurotransmission but inhibits presynaptic GABA(B) receptors in nucleus accumbens neurons". PMID 9514305. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)



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