Tauroursodeoxycholic acid
Synonym(s):Sodium Tauroursodeoxycholate;Tauroursodeoxycholic Acid, Sodium Salt - CAS 14605-22-2 - Calbiochem
- CAS NO.:14605-22-2
- Empirical Formula: C26H45NO6S
- Molecular Weight: 499.7
- MDL number: MFCD00069496
- EINECS: 1308068-626-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-27 17:30:58
What is Tauroursodeoxycholic acid?
Toxicity
There is no information available regarding the LD50 and overdose of tauroursodeoxycholic acid.
Description
Tauroursodeoxycholic acid (TUDCA) is a hydrophilic bile acid synthesized in hepatocytes by the conjugation of ursodeoxycholic acid (UDCA) with the amino acid taurine. UDCA, which is made by gut bacteria, is FDAapproved in the United States for the treatment of certain cholestatic liver diseases. Humans make TUDCA to some extent, but it is found in copious amounts in the bile of bears. TUDCA is a classic inhibitor of endoplasmic reticulum (ER) stress. Reduces ER stress and adipose tissue inflammation in a mouse model of high fat diet-induced obesity. Blocks ER stress-induced NLRP3 inflammasome activation and hepatocyte death. Attenuates amyloid precursor protein processing and amyloid-β deposition in APP/PS1 mouse model.
The Uses of Tauroursodeoxycholic acid
Tauroursodeoxycholic acid (TUDCA) is a water-soluble bile salt naturally occurring in the body. When bile salts reach the intestines, they can be metabolized by bacteria into ursodeoxycholic acid (UDCA). TUDCA is formed when taurine binds to UDCA. TUDCA is used to treat cholestasis, a condition in which bile fails to flow from the liver to the duodenum. TUDCA, UDCA, and other soluble bile salts can counteract the toxicity of regular bile acids when the latter are backed up in the liver. TUDCA is also used to treat cholesterol gallstones, dissolving them to a size in which they may be passed.
What are the applications of Application
Tauroursodeoxycholic Acid, Sodium Salt is a bile related salt for isolation of lipids and membrane-bound proteins
Background
Tauroursodeoxycholic acid, also known as ursodoxicoltaurine, is a highly hydrophilic tertiary bile acid that is produced in humans at a low concentration. It is a taurine conjugate of ursodeoxycholic acid with comparable therapeutic efficacy and safety, but a much higher hydrophilicity. Normally, hydrophilic bile acids regulates hydrophobic bile acids and their cytotoxic effects. Tauroursodeoxycholic acid can reduce the absorption of cholesterol in the small intestine, thereby reducing the body's intake of dietary cholesterol and the body cholesterol content.
Tauroursodeoxycholic acid is currently used in Europe to treat and prevent gallstones as a bile acid derivative. Due to a range of its molecular properties - namely its anti-apoptotic effects - tauroursodeoxycholic acid has been examined in inflammatory metabolic diseases and neurodegenerative diseases.
Indications
Tauroursodeoxycholic acid is used to prevent and treat gallstone formation.
Tauroursodeoxycholic acid is used in combination with phenylbutyric acid to treat amyotrophic lateral sclerosis (ALS) in adults.
Pharmacokinetics
Tauroursodeoxycholic acid works to decrease bile acid and cholesterol levels. It reduces the cholesterol content and increases the bile acid content in gallbladder bile to prevent the formation of cholesterol gallstones.
Tauroursodeoxycholic acid possesses anti-apoptotic and anti-inflammatory properties. These findings provoked the investigations of tauroursodeoxycholic acid as a potential therapeutic agent for neurodegenerative diseases, such as amyotrophic lateral sclerosis, Alzheimer's disease, and Parkinson's disease. Other studies also suggest that tauroursodeoxycholic acid can promote angiogenesis and suppress adipogenesis of adipose-derived mesenchymal stem cells (MSCs). Anti-osteoporotic effects of tauroursodeoxycholic acid have also been documented, as it was shown to enhance osteogenic differentiation of bone marrow-derived MSCs.
Metabolism
There is little biotransformation of tauroursodeoxycholic acid. It is partially deconjugated by intestinal microflora to form unconjugated bile acids.
Properties of Tauroursodeoxycholic acid
Melting point: | 173-175°C |
Density | 1.216±0.06 g/cm3(Predicted) |
storage temp. | +15C to +30C |
solubility | Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 20 mg/ml with warming) |
form | solid |
color | White |
Safety information for Tauroursodeoxycholic acid
Computed Descriptors for Tauroursodeoxycholic acid
InChIKey | BHTRKEVKTKCXOH-LBSADWJPSA-N |
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