tauroursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 4746

Abbreviated name: TUDA
Synonyms: Relyvrio® (sodium phenylbutyrate + taurursodiol) | tauroursodeoxycholate | taurursodiol | TUDCA | UR 906 | ursodoxicoltaurine (INN)
Approved drug PDB Ligand Immunopharmacology Ligand
tauroursodeoxycholic acid is an approved drug (FDA (2022))
Comment: Tauroursodeoxycholic acid (TUDCA) is a conjugated bile acid derivative. Evidence suggests that it acts as a chemical chaperone and facilitates protein folding within the endoplasmic reticulum [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 132.31
Molecular weight 499.3
XLogP 4.86
No. Lipinski's rules broken 0
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Isomeric SMILES O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCCS(=O)(=O)O)C)C)O)C
InChI InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
1. Alqallaf A, Cates DW, Render KP, Patel KA. (2024)
Sodium Phenylbutyrate and Taurursodiol: A New Therapeutic Option for the Treatment of Amyotrophic Lateral Sclerosis.
Ann Pharmacother, 58 (2): 165-173. [PMID:37269231]
2. Cao SS, Zimmermann EM, Chuang BM, Song B, Nwokoye A, Wilkinson JE, Eaton KA, Kaufman RJ. (2013)
The unfolded protein response and chemical chaperones reduce protein misfolding and colitis in mice.
Gastroenterology, 144 (5): 989-1000.e6. [PMID:23336977]
3. Elmansy MF, Reidl CT, Rahaman M, Özdinler PH, Silverman RB. (2023)
Small molecules targeting different cellular pathologies for the treatment of amyotrophic lateral sclerosis.
Med Res Rev, 43 (6): 2260-2302. [PMID:37243319]
4. Meier PJ, Eckhardt U, Schroeder A, Hagenbuch B, Stieger B. (1997)
Substrate specificity of sinusoidal bile acid and organic anion uptake systems in rat and human liver.
Hepatology, 26 (6): 1667-77. [PMID:9398014]
5. Paganoni S, Hendrix S, Dickson SP, Knowlton N, Macklin EA, Berry JD, Elliott MA, Maiser S, Karam C, Caress JB et al.. (2021)
Long-term survival of participants in the CENTAUR trial of sodium phenylbutyrate-taurursodiol in amyotrophic lateral sclerosis.
Muscle Nerve, 63 (1): 31-39. [PMID:33063909]
6. Paganoni S, Macklin EA, Hendrix S, Berry JD, Elliott MA, Maiser S, Karam C, Caress JB, Owegi MA, Quick A et al.. (2020)
Trial of Sodium Phenylbutyrate-Taurursodiol for Amyotrophic Lateral Sclerosis.
N Engl J Med, 383 (10): 919-930. [PMID:32877582]
7. Wang W, Zhao J, Gui W, Sun D, Dai H, Xiao L, Chu H, Du F, Zhu Q, Schnabl B et al.. (2018)
Tauroursodeoxycholic acid inhibits intestinal inflammation and barrier disruption in mice with non-alcoholic fatty liver disease.
Br J Pharmacol, 175 (3): 469-484. [PMID:29139555]
8. Zangerolamo L, Vettorazzi JF, Rosa LRO, Carneiro EM, Barbosa HCL. (2021)
The bile acid TUDCA and neurodegenerative disorders: An overview.
Life Sci, 272: 119252. [PMID:33636170]