Tramiprosate
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MedKoo CAT#: 531036

CAS#: 3687-18-1

Description: Tramiprosate, also known as homotaurine, is a gamma-Aminobutyric acid (GABA) receptor agonist and a glycosaminoglycan mimetic used in the treatment of Alzheimer's disease.


Chemical Structure

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Tramiprosate
CAS# 3687-18-1

Theoretical Analysis

MedKoo Cat#: 531036
Name: Tramiprosate
CAS#: 3687-18-1
Chemical Formula: C3H9NO3S
Exact Mass: 139.0303
Molecular Weight: 139.169
Elemental Analysis: C, 25.89; H, 6.52; N, 10.06; O, 34.49; S, 23.04

Price and Availability

Size Price Availability Quantity
2.0g USD 150.0 2 Weeks
5.0g USD 350.0 2 Weeks
10.0g USD 650.0 2 Weeks
25.0g USD 950.0 2 Weeks
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Related CAS #: 3687-18-1 (free)   14650-46-5 (sodium)  

Synonym: Tramiprosate, Tramiprosate Na, Tramiprosate sodium, Alzhemed, Homotaurine, NC-758, NC 758, NC758

IUPAC/Chemical Name: 3-aminopropane-1-sulfonic acid

InChi Key: SNKZJIOFVMKAOJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)

SMILES Code: O=S(CCCN)(O)=O

Appearance: White to off-white crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 139.169 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Wu S, Yue Y, Tian H, Tao L, Wang Y, Xiang J, Wang S, Ding H. Tramiprosate protects neurons against ischemic stroke by disrupting the interaction between PSD95 and nNOS. Neuropharmacology. 2014 Aug;83:107-17. doi: 10.1016/j.neuropharm.2014.04.010. Epub 2014 Apr 24. PubMed PMID: 24769446.

2: Wright TM. Tramiprosate. Drugs Today (Barc). 2006 May;42(5):291-8. Review. PubMed PMID: 16801992.

3: Caltagirone C, Ferrannini L, Marchionni N, Nappi G, Scapagnini G, Trabucchi M. The potential protective effect of tramiprosate (homotaurine) against Alzheimer's disease: a review. Aging Clin Exp Res. 2012 Dec;24(6):580-7. doi: 10.3275/8585. Epub 2012 Sep 5. Review. PubMed PMID: 22961121.

4: Rao RN, Maurya PK, Shinde DD, Agwane SB. Reversed-phase liquid chromatographic determination of tramiprosate in rat plasma using evaporative light scattering detector. Biomed Chromatogr. 2011 Aug;25(8):925-9. doi: 10.1002/bmc.1546. Epub 2010 Dec 10. PubMed PMID: 21154641.

5: Gauthier S, Aisen PS, Ferris SH, Saumier D, Duong A, Haine D, Garceau D, Suhy J, Oh J, Lau W, Sampalis J. Effect of tramiprosate in patients with mild-to-moderate Alzheimer's disease: exploratory analyses of the MRI sub-group of the Alphase study. J Nutr Health Aging. 2009 Jun;13(6):550-7. Erratum in: J Nutr Health Aging. 2010 Jan;14(1):80. PubMed PMID: 19536424.

6: Aisen PS, Gauthier S, Ferris SH, Saumier D, Haine D, Garceau D, Duong A, Suhy J, Oh J, Lau WC, Sampalis J. Tramiprosate in mild-to-moderate Alzheimer's disease - a randomized, double-blind, placebo-controlled, multi-centre study (the Alphase Study). Arch Med Sci. 2011 Feb;7(1):102-11. doi: 10.5114/aoms.2011.20612. Epub 2011 Mar 8. PubMed PMID: 22291741; PubMed Central PMCID: PMC3258678.

7: Rao RN, Maurya PK, Shinde DD, Khalid S. Precolumn derivatization followed by liquid chromatographic separation and determination of tramiprosate in rat plasma by fluorescence detector: application to pharmacokinetics. J Pharm Biomed Anal. 2011 May 15;55(2):282-7. doi: 10.1016/j.jpba.2011.01.013. Epub 2011 Jan 22. PubMed PMID: 21324628.

8: Saumier D, Duong A, Haine D, Garceau D, Sampalis J. Domain-specific cognitive effects of tramiprosate in patients with mild to moderate Alzheimer's disease: ADAS-cog subscale results from the Alphase Study. J Nutr Health Aging. 2009 Nov;13(9):808-12. PubMed PMID: 19812871.

9: Gervais F, Paquette J, Morissette C, Krzywkowski P, Yu M, Azzi M, Lacombe D, Kong X, Aman A, Laurin J, Szarek WA, Tremblay P. Targeting soluble Abeta peptide with Tramiprosate for the treatment of brain amyloidosis. Neurobiol Aging. 2007 Apr;28(4):537-47. Epub 2006 May 3. PubMed PMID: 16675063.

10: Greenberg SM, Rosand J, Schneider AT, Creed Pettigrew L, Gandy SE, Rovner B, Fitzsimmons BF, Smith EE, Edip Gurol M, Schwab K, Laurin J, Garceau D. A phase 2 study of tramiprosate for cerebral amyloid angiopathy. Alzheimer Dis Assoc Disord. 2006 Oct-Dec;20(4):269-74. PubMed PMID: 17132972.

11: Saumier D, Aisen PS, Gauthier S, Vellas B, Ferris SH, Duong A, Suhy J, Oh J, Lau W, Garceau D, Haine D, Sampalis J. Lessons learned in the use of volumetric MRI in therapeutic trials in Alzheimer's disease: the ALZHEMED (Tramiprosate) experience. J Nutr Health Aging. 2009 Apr;13(4):370-2. PubMed PMID: 19300884.

12: Kocis P, Tolar M, Yu J, Sinko W, Ray S, Blennow K, Fillit H, Hey JA. Elucidating the Aβ42 Anti-Aggregation Mechanism of Action of Tramiprosate in Alzheimer's Disease: Integrating Molecular Analytical Methods, Pharmacokinetic and Clinical Data. CNS Drugs. 2017 Jun;31(6):495-509. doi: 10.1007/s40263-017-0434-z. PubMed PMID: 28435985.

13: Habchi J, Arosio P, Perni M, Costa AR, Yagi-Utsumi M, Joshi P, Chia S, Cohen SI, Müller MB, Linse S, Nollen EA, Dobson CM, Knowles TP, Vendruscolo M. An anticancer drug suppresses the primary nucleation reaction that initiates the production of the toxic Aβ42 aggregates linked with Alzheimer's disease. Sci Adv. 2016 Feb 12;2(2):e1501244. doi: 10.1126/sciadv.1501244. eCollection 2016 Feb. PubMed PMID: 26933687; PubMed Central PMCID: PMC4758743.

14: Ricciardi L, De Nigris F, Specchia A, Fasano A. Homotaurine in Parkinson's disease. Neurol Sci. 2015 Sep;36(9):1581-7. doi: 10.1007/s10072-015-2201-6. Epub 2015 Apr 19. PubMed PMID: 25894843.

15: Russo R, Adornetto A, Cavaliere F, Varano GP, Rusciano D, Morrone LA, Corasaniti MT, Bagetta G, Nucci C. Intravitreal injection of forskolin, homotaurine, and L-carnosine affords neuroprotection to retinal ganglion cells following retinal ischemic injury. Mol Vis. 2015 Jun 29;21:718-29. eCollection 2015. PubMed PMID: 26167113; PubMed Central PMCID: PMC4483367.

16: Santa-Maria I, Hernández F, Del Rio J, Moreno FJ, Avila J. Tramiprosate, a drug of potential interest for the treatment of Alzheimer's disease, promotes an abnormal aggregation of tau. Mol Neurodegener. 2007 Sep 6;2:17. PubMed PMID: 17822548; PubMed Central PMCID: PMC2048960.

17: Brener O, Dunkelmann T, Gremer L, van Groen T, Mirecka EA, Kadish I, Willuweit A, Kutzsche J, Jürgens D, Rudolph S, Tusche M, Bongen P, Pietruszka J, Oesterhelt F, Langen KJ, Demuth HU, Janssen A, Hoyer W, Funke SA, Nagel-Steger L, Willbold D. QIAD assay for quantitating a compound's efficacy in elimination of toxic Aβ oligomers. Sci Rep. 2015 Sep 23;5:13222. doi: 10.1038/srep13222. PubMed PMID: 26394756; PubMed Central PMCID: PMC4585794.

18: Spalletta G, Cravello L, Gianni W, Piras F, Iorio M, Cacciari C, Casini AR, Chiapponi C, Sancesario G, Fratangeli C, Orfei MD, Caltagirone C, Piras F. Homotaurine Effects on Hippocampal Volume Loss and Episodic Memory in Amnestic Mild Cognitive Impairment. J Alzheimers Dis. 2016;50(3):807-16. doi: 10.3233/JAD-150484. PubMed PMID: 26757035.

19: Mutolo MG, Albanese G, Rusciano D, Pescosolido N. Oral Administration of Forskolin, Homotaurine, Carnosine, and Folic Acid in Patients with Primary Open Angle Glaucoma: Changes in Intraocular Pressure, Pattern Electroretinogram Amplitude, and Foveal Sensitivity. J Ocul Pharmacol Ther. 2016 Apr;32(3):178-83. doi: 10.1089/jop.2015.0121. Epub 2016 Jan 15. PubMed PMID: 26771282.

20: Wang P, Ding K. Proteoglycans and glycosaminoglycans in misfolded proteins formation in Alzheimer's disease. Protein Pept Lett. 2014;21(10):1048-56. Review. PubMed PMID: 24975673.