10218. Tramiprosate

Nomenclature

CAS number: 3687-18-1
3-Amino-1-propanesulfonic acid; γ-aminopropanesulfonic acid; 3-sulfopropylamine; homotaurine; NC-531; NC-758; Alzhemed; Cerebril (Neurochem).
C3H9NO3S; mol wt 139.17.
C 25.89%, H 6.52%, N 10.06%, O 34.49%, S 23.04%.

Description and references

Sulfonic acid analog of γ-aminobutyric acid (GABA), q.v. Binds to soluble amyloid β peptide (Aβ), q.v., and inhibits fibrillization and plaque formation. Prepn: S. Gabriel, W. E. Lauer, Ber. 23, 87 (1890); P. Rumpf, Compt. Rend. 204, 592 (1937). Large scale synthesis from 1,3-propane sultone: X. Kong et al., WO 04113391; eidem, US 050143462 (2004, 2005 both to Neurochem). Crystal structure: K. Tomita, Tetrahedron Lett. 12, 2587 (1971) DOI. GABA mimetic activity: R. G. Fariello, G. T. Golden, Brain Res. Bull. 5, Suppl. 2, 691 (1980) DOI. Pharmacology and binding to Aβ: F. Gervais et al., Neurobiol. Aging 28, 537 (2007) DOI PubMed. Pharmacokinetics in patients with cerebral amyloid angiopathy: S. M. Greenberg et al., Alzheimer Dis. Assoc. Disord. 20, 269 (2006) DOI PubMed. Clinical effect on Aβ42 levels in CSF of Alzheimer's patients: P. S. Aisen et al., Neurology 67, 1757 (2006) DOI PubMed.

Chemical structure

Properties

White crystalline powder, mp 292°. Irritant. Crystal density: 1.610 (α-form); 1.599 (β-form). pKa2 10.05. Sol in water; slightly sol in ethanol.

Derivative

Sodium salt.

Nomenclature

CAS number: 14650-46-5
C3H8NNaO3S; mol wt 161.16.
C 22.36%, H 5.00%, N 8.69%, Na 14.27%, O 29.78%, S 19.90%.

Properties

White crystalline powder from ethanol, mp 198-199°.

Therapeutic Category

Antiamyloidogenic agent; in treatment of Alzheimer's disease.

Keywords

Antiamyloidogenic