Homotaurine

Homotaurine[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
3-Aminopropane-1-sulfonic acid
Other names
Tramiprosate; Alzhemed; 3-APS
Identifiers
3687-18-1 Yes
ChEMBL ChEMBL149082 Yes
ChemSpider 1584 Yes
Jmol-3D images Image
KEGG D06202 Yes
PubChem 1646
Properties
Molecular formula
 C3H9NO3S
Molar mass 139.17 g·mol−1
Melting point 293 °C (559 °F; 566 K) (decomposition)
Hazards
R-phrases R36/37/38
S-phrases S26 S36
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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 has also been investigated as a potential treatment for Alzheimer's disease.[3] It binds to soluble amyloid beta and inhibits the formation of neurotoxic aggregates that lead to amyloid plaque deposition in the brain.[4] However, clinical trials failed to show improvement compared to placebo.[5][6][7]

Homotaurine is a zwitterion at neutral pH.

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

See also

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.
  3. ↑ Gauthier, S; Aisen, P. S.; Ferris, S. H.; Saumier, D; Duong, A; Haine, D; Garceau, D; Suhy, J; Oh, J; Lau, W; Sampalis, J (2009). "Effect of tramiprosate in patients with mild-to-moderate Alzheimer's disease: Exploratory analyses of the MRI sub-group of the Alphase study". The journal of nutrition, health & aging 13 (6): 550–7. PMID 19536424.
  4. ↑ Aisen PS, Gauthier S, Vellas B et al. (2007). "Alzhemed: a potential treatment for Alzheimer's disease". Curr Alzheimer Res 4 (4): 473–8. doi:10.2174/156720507781788882. PMID 17908052.
  5. ↑ "Tramiprosate Falls Short in Phase III Alzheimer's Trial". Clinical Psychiatry News. November 1, 2007.
  6. ↑ "Drugs In Clinical Trials : Alzhemed". Alzheimer Research Forum. Retrieved 1 October 2011.
  7. ↑ "Analysts Skeptical Of Neurochem's Efforts To Salvage Value From Alzhemed". Canada National Post. November 13, 2007. Retrieved 1 October 2011.