tauroursodeoxycholic acid

Also known as tauroursodeoxycholate, TUDA, TUDCA, 3alpha,7beta-dihydroxy-5beta-cholanoyltaurine, N-ursodeoxycholoyltaurine, 2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonic acid, N-(3alpha,7beta-dihydroxy-5beta-cholan-24-oyl)taurine, Ursodeoxycholyltaurine

Ursodoxicoltaurine is the international nonproprietary name (INN) for the pharmaceutical form of tauroursodeoxycholic acid (TUDCA). It is also known as taurursodiol. Tauroursodeoxycholic acid is a naturally occurring hydrophilic bile acid which is the taurine conjugated form of ursodeoxycholic acid (UDCA). Humans have only trace amounts of tauroursodeoxycholic acid but bears have large amounts of tauroursodeoxycholic acid and ursodeoxycholic acid in their bile.

Chemical data

Formula: C26H45NO6S
Molecular weight: 499.7 g/mol
IUPAC name: 2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
SMILES: C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChIKey: BHTRKEVKTKCXOH-LBSADWJPSA-N
XLogP: 3.6
Polar surface area: 132 Å²
H-bond donors: 4
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2022
Admin. routes: oral
Indications: neurodegenerative disease, amyotrophic lateral sclerosis

via ChEMBL · EBI

Research

1,329 papers

Tauroursodeoxycholic acid: a potential therapeutic tool in neurodegenerative diseases.Translational neurodegeneration · 2022
Tauroursodeoxycholic Acid Improves Nonalcoholic Fatty Liver Disease by Regulating Gut Microbiota and Bile Acid Metabolism.Journal of agricultural and food chemistry · 2024
Tauroursodeoxycholic acid ameliorates renal injury induced by COL4A3 mutation.Kidney international · 2024
Neuroprotective Effect of Tauroursodeoxycholic Acid (TUDCA) on In Vitro and In Vivo Models of Retinal Disorders: A Systematic Review.Current neuropharmacology · 2024
Sodium Phenylbutyrate and Tauroursodeoxycholic Acid: A Story of Hope Turned to Disappointment in Amyotrophic Lateral Sclerosis Treatment.Clinical drug investigation · 2024

via PubMed

Wikidata facts

Subclass of: sterol
Has part: sulfur
Mass: 499.297
Has use: medication

Show 5 more facts

chemical formula: C₂₆H₄₅NO₆S
isomeric SMILES: C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
canonical SMILES: CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
Commons category: Tauroursodeoxycholic acid
stereoisomer of: taurochenodeoxycholic acid

Sources (4)

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Encyclopedic overview

9 sections

Contents

Synthesis
Medical uses
Cellular mechanisms
Research
Photoreceptor cells
Choroidal neovascularization
Synaptic connectivity
Other diseases
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477861058 | ImageFile=Tauroursodeoxycholic acid.svg | ImageSize=200 | IUPACName=2-(3α,7β-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid | SystematicName=2-{(4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid | OtherNames=Tauroursodeoxycholic acid; TUDCA; 3α,7β-Dihydroxy-5β-cholanoyltaurine; UR 906; Ursodeoxycholyltaurine; Taurursodiol |Section1= |Section2= |Section3= | Section6 = }}

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