Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H44NO6S.Na |
Molecular Weight | 521.685 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS([O-])(=O)=O
InChI
InChIKey=YXHRQQJFKOHLAP-FVCKGWAHSA-M
InChI=1S/C26H45NO6S.Na/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3;/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/q;+1/p-1/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-;/m1./s1
Molecular Formula | C26H44NO6S |
Molecular Weight | 498.696 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26759227Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25664595 | https://www.ncbi.nlm.nih.gov/pubmed/23592128 | https://www.ncbi.nlm.nih.gov/pubmed/20522594
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26759227
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25664595 | https://www.ncbi.nlm.nih.gov/pubmed/23592128 | https://www.ncbi.nlm.nih.gov/pubmed/20522594
Sodium taurodeoxycholate is a bile salt-related, anionic detergent used for isolation of membrane proteins including inner mitochondrial membrane proteins. It is formed by the conjugation of ursodeoxycholic acid (UDCA) with taurine. Sodium taurodeoxycholate and ursodeoxycholic acid are major constituents of black bear bile, which has been used in traditional Chinese medicine for thousands of years. Bear bile was historically employed to treat a number of diseases including jaundice, summer diarrhea, abdominal pain due to hepatobiliary diseases and gastric malfunction, biliary ascariasis, infectious skin diseases, the common cold, intestinal worms, and inflammation of the throat. Sodium taurodeoxycholate has been shown to inhibit apoptosis by modulating mitochondrial membrane perturbation and pore formation, B cell lymphoma 2 (Bcl-2)-associated protein X (BAX) translocation, cytochrome c release, and caspase activation. Sodium taurodeoxycholate inhibits amyloid beta (Ab)-induced apoptosis and attenuates the endoplasmic reticulum (ER) stress, which are thought to be key components of the pathological process in certain diseases. In clinical studies, Sodium taurodeoxycholate is shown to be very safe with oral administration of 1500 mg/day for up to 6 months. In a more recent clinical study, a dose of 1750 mg/day for up to 4 weeks was well tolerated in healthy obese persons. One of the major adverse effects of Sodium taurodeoxycholate is diarrhea. Based on the related information from ursodeoxycholic acid, other gastrointestinal side effects are possible including abdominal pain, flatulence, nausea, dyspepsia, and anorexia.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26435512 |
680.0 nM [EC50] | ||
Target ID: CHEMBL1743128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12523936 |
60.0 µM [IC50] | ||
Target ID: CHEMBL4847 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12842829 |
|||
Target ID: gallbladder eicosanoid release Sources: https://www.ncbi.nlm.nih.gov/pubmed/7708818 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells]. | 2003 May |
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Hepatic overexpression of murine Abcb11 increases hepatobiliary lipid secretion and reduces hepatic steatosis. | 2004 Jan 23 |
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The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. | 2007 Sep |
|
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species. | 2011 Feb 3 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25664595
Tauroursodeoxycholic acid 1 g twice daily by mouth
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9537871
Isolated rat hepatocytes were cultured in uncoated culture dishes (1x10^6 cells per plate) and treated with bile acids for 4 to 24 h. After treatment, the tissue-culture supernatant was harvested and assayed for enzymatic activity of lactate dehydrogenase (LDH) and aspartate aminotransferase (AST). Enzymatic activity was determined in accordance with standard techniques, using commercially available standard kits (Boehringer Mannheim, Germany).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:05:34 GMT 2023
by
admin
on
Fri Dec 15 15:05:34 GMT 2023
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Record UNII |
5PE424S83L
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C83486
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23664773
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C80659
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1180-95-6
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5PE424S83L
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1364852
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214-652-0
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300000023938
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DTXSID00922591
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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