Homotaurine

Homotaurine^[1]
Names
	Preferred IUPAC name 3-Aminopropane-1-sulfonic acid
	Other names Tramiprosate; Alzhemed; 3-APS
Identifiers
CAS Number	3687-18-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1457;
ChEMBL	ChEMBL149082 ;
ChemSpider	1584 ;
DrugBank	DB06527;
ECHA InfoCard	100.020.889
EC Number	222-977-4;
KEGG	D06202 ;
PubChem CID	1646;
UNII	5K8EAX0G53 ;
CompTox Dashboard (EPA)	DTXSID80190352 ;
	InChI InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7) Key: SNKZJIOFVMKAOJ-UHFFFAOYSA-N ; InChI=1/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7) Key: SNKZJIOFVMKAOJ-UHFFFAOYAT;
	SMILES O=S(=O)(O)CCCN;
Properties
Chemical formula	C3H9NO3S
Molar mass	139.17 g·mol−1
Melting point	293 °C (559 °F; 566 K) (decomposition)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Homotaurine, also known as tramiprosate (INN), 3-amino-1-propanesulfonic acid, or 3-APS, is a natural sulfonic acid found in seaweed.^[3] It is analogous to taurine, but with an extra carbon in its chain. It has GABAergic activity, apparently by mimicking GABA, which it resembles.^[4]

Homotaurine was investigated in a Phase III clinical trial as a potential treatment for Alzheimer's disease (AD) that did not show efficacy. However, post-hoc analyses have shown positive and significant effects of homotaurine on secondary endpoints and subgroups of patients, including a reduction in hippocampal volume loss and lower decline in memory function in the overall cohort, as well as a reduction in global cognitive decline in APOE4 allele carriers, suggesting a disease-modifying effect.^[5] A study in cognitive impairment done in 2018 did show positive benefits.^[6]

Homotaurine is currently in a phase 3 study with expected FDA approval as the first disease modifying drug for AD.^[7]^[8]

^ "Homotaurine". Sigma-Aldrich.
^ "Tramiprosate". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.
^ Martorana, Alessandro; Di Lorenzo, Francesco; Manenti, Guglielmo; Semprini, Roberta; Koch, Giacomo (23 September 2014). "Homotaurine Induces Measurable Changes of Short Latency Afferent Inhibition in a Group of Mild Cognitive Impairment Individuals". Frontiers in Aging Neuroscience. 6: 254. doi:10.3389/fnagi.2014.00254. PMC 4172065. PMID 25295005.
^ Cite error: The named reference OrgChem2007 was invoked but never defined (see the help page).
^ Caltagirone, C; Ferrannini, L; Marchionni, N; Nappi, G; Scapagnini, G; Trabucchi, M (December 2012). "The potential protective effect of tramiprosate (homotaurine) against Alzheimer's disease: a review". Aging Clinical and Experimental Research. 24 (6): 580–587. doi:10.3275/8585. PMID 22961121. S2CID 10816430.
^ Martorana, A.; Motta, C; Koch, G.; Massaia, M.; Mondino, S.; Raniero, I.; Vacca, A.; Di Lorenzo, F.; Cavallo, G.; Oddenino, E.; Pavanelli, E.; Maniscalco, M.; Montano, V.; Mastropietro, A.; Bellia, N. C.; Ciravegna, E.; La Rocca, M.; Vitale, E.; Lorico, F.; Zacchettin, B.; Scalise, A.; Codemo, A.; Gabelli, C.; Spano, M.; Poli, S.; Panuccio, D.; Bruno, P.; Alfieri, P.; Ruggiero, R.; Cursi, F.; Levi Della Vida, G. (15 March 2018). "Effect of homotaurine in patients with cognitive impairment: results from an Italian observational retrospective study". Journal of Gerontology and Geriatrics. 66: 15–20.
^ Tolar, Martin; Abushakra, Susan; Hey, John A.; Porsteinsson, Anton; Sabbagh, Marwan (December 2020). "Aducanumab, gantenerumab, BAN2401, and ALZ-801—the first wave of amyloid-targeting drugs for Alzheimer's disease with potential for near term approval". Alzheimer's Research & Therapy. 12 (1): 95. doi:10.1186/s13195-020-00663-w. PMC 7424995. PMID 32787971.
^ Abushakra, S.; Porsteinsson, A.; Scheltens, P.; Sadowsky, C.; Vellas, B.; Cummings, J.; Gauthier, S.; Hey, J. A.; Power, A.; Wang, P.; Tolar, M.; Tolar, M (1 September 2017). "Clinical effects of tramiprosate in apoe4/4 homozygous patients with mild alzheimer's disease suggest disease modification potential". Journal of Prevention of Alzheimer's Disease. 4 (3): 149–156. doi:10.14283/jpad.2017.26. PMID 29182706. S2CID 44515548.

[1] "Homotaurine". Sigma-Aldrich.

[2] "Tramiprosate". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.

[3] Martorana, Alessandro; Di Lorenzo, Francesco; Manenti, Guglielmo; Semprini, Roberta; Koch, Giacomo (23 September 2014). "Homotaurine Induces Measurable Changes of Short Latency Afferent Inhibition in a Group of Mild Cognitive Impairment Individuals". Frontiers in Aging Neuroscience. 6: 254. doi:10.3389/fnagi.2014.00254. PMC 4172065. PMID 25295005.

[OrgChem2007-4] Cite error: The named reference OrgChem2007 was invoked but never defined (see the help page).

[AD2012rev-5] Caltagirone, C; Ferrannini, L; Marchionni, N; Nappi, G; Scapagnini, G; Trabucchi, M (December 2012). "The potential protective effect of tramiprosate (homotaurine) against Alzheimer's disease: a review". Aging Clinical and Experimental Research. 24 (6): 580–587. doi:10.3275/8585. PMID 22961121. S2CID 10816430.

[6] Martorana, A.; Motta, C; Koch, G.; Massaia, M.; Mondino, S.; Raniero, I.; Vacca, A.; Di Lorenzo, F.; Cavallo, G.; Oddenino, E.; Pavanelli, E.; Maniscalco, M.; Montano, V.; Mastropietro, A.; Bellia, N. C.; Ciravegna, E.; La Rocca, M.; Vitale, E.; Lorico, F.; Zacchettin, B.; Scalise, A.; Codemo, A.; Gabelli, C.; Spano, M.; Poli, S.; Panuccio, D.; Bruno, P.; Alfieri, P.; Ruggiero, R.; Cursi, F.; Levi Della Vida, G. (15 March 2018). "Effect of homotaurine in patients with cognitive impairment: results from an Italian observational retrospective study". Journal of Gerontology and Geriatrics. 66: 15–20.

[Tolar_et_al_2020-7] Tolar, Martin; Abushakra, Susan; Hey, John A.; Porsteinsson, Anton; Sabbagh, Marwan (December 2020). "Aducanumab, gantenerumab, BAN2401, and ALZ-801—the first wave of amyloid-targeting drugs for Alzheimer's disease with potential for near term approval". Alzheimer's Research & Therapy. 12 (1): 95. doi:10.1186/s13195-020-00663-w. PMC 7424995. PMID 32787971.

[8] Abushakra, S.; Porsteinsson, A.; Scheltens, P.; Sadowsky, C.; Vellas, B.; Cummings, J.; Gauthier, S.; Hey, J. A.; Power, A.; Wang, P.; Tolar, M.; Tolar, M (1 September 2017). "Clinical effects of tramiprosate in apoe4/4 homozygous patients with mild alzheimer's disease suggest disease modification potential". Journal of Prevention of Alzheimer's Disease. 4 (3): 149–156. doi:10.14283/jpad.2017.26. PMID 29182706. S2CID 44515548.

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