| Size | Price | Stock | Qty |
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| 25mg |
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| Targets |
Active metabolite of obeticholic acid; FXR
Tauro-Obeticholic acid targets the farnesoid X receptor (FXR), a nuclear receptor that regulates the expression of genes involved in bile acid, lipid, and glucose metabolism. As a potent FXR agonist, it activates FXR signaling, leading to the repression of bile acid synthesis and modulation of lipid and glucose homeostasis. |
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| ln Vitro |
Microorganisms in the ileum and colon can cleave taurobeticholic acid and transform it into the parent drug, which can subsequently be reabsorbed or expelled in the feces. Obeticholic acid interacts with taurine in the liver to create taurobeticholic acid, which is secreted into the bile [1].
In vitro, Tauro-Obeticholic acid functions as a potent FXR agonist. It activates FXR signaling, regulating the expression of genes involved in bile acid synthesis and metabolism. Its activity is similar to its parent compound, Obeticholic acid, which is an orally bioavailable FXR agonist. It is used as a research tool to study FXR-mediated pathways in metabolic and liver diseases. |
| ln Vivo |
In vivo, Tauro-Obeticholic acid is an active metabolite of Obeticholic acid, formed by conjugation with taurine. It is secreted into bile and contributes to the overall pharmacological activity of the parent drug. Its role in vivo is primarily understood through pharmacokinetic and pharmacodynamic studies, where its concentration is correlated with FXR activation and metabolic effects.
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| Enzyme Assay |
In vitro assays for Tauro-Obeticholic acid typically involve measuring its activation of FXR. A luciferase reporter gene assay is used where cells are transfected with an FXR expression plasmid and a reporter plasmid containing FXR response elements. The compound is added at various concentrations, and luciferase activity is measured. EC50 values are calculated from dose-response curves.
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| Cell Assay |
For in vitro cell-based assays, hepatocytes or other cells expressing FXR are cultured and treated with Tauro-Obeticholic acid at various concentrations. FXR activation is confirmed by measuring the expression of FXR target genes (e.g., SHP, BSEP, CYP7A1) by qRT-PCR. Cell viability is assessed by standard assays. The compound's effects on lipid and glucose metabolism can be assessed in relevant cell models.
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| Animal Protocol |
In vivo animal studies with Tauro-Obeticholic acid are conducted in models of metabolic and liver diseases. The compound is administered orally to rodents. Efficacy is measured by assessing markers of bile acid metabolism, lipid profiles, and glucose homeostasis. Liver histology is examined for signs of fibrosis or steatosis. The compound's effects on FXR target gene expression are analyzed in liver tissues.
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| ADME/Pharmacokinetics |
Tauro-Obeticholic acid (CAS: 863239-61-6) has a molecular weight of 527.76 g/mol and a molecular formula of C28H49NO6S. Appearance: solid powder. Purity: ≥98%. Storage: powder at -20°C. The compound is a taurine-conjugated active metabolite of Obeticholic acid and a potent FXR agonist.
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| Toxicity/Toxicokinetics |
Tauro-Obeticholic acid is a research compound and is not approved for human therapeutic use. In preclinical studies, it has shown a manageable safety profile. As a FXR agonist, it may have effects on bile acid metabolism and liver function. Standard laboratory safety precautions should be followed when handling the compound. Comprehensive toxicology studies would be required for therapeutic development.
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| References | |
| Additional Infomation |
Ocaliva™ is a farnesoid X receptor (FXR) agonist developed by Intercept Pharmaceuticals for the treatment of a Obeticholic of liver diseases. It recently received accelerated approval in the United States for the treatment of primary biliary cholangitis, either in combination with ursodeoxycholic acid (UDCA) in adult patients who have not responded to UDCA, or as monotherapy in adult patients who cannot tolerate UDCA. It is currently undergoing pre-registration for this indication in the European Union. This article summarizes the key milestones in the development of obeticholic acid that ultimately led to its first approval for the treatment of primary biliary cholangitis. [1]
Tauro-Obeticholic acid is the taurine-conjugated active metabolite of Obeticholic acid (OCA), a potent FXR agonist. It has the CAS number 863239-61-6 and a molecular weight of 527.76 g/mol. It plays a key role in regulating bile acid synthesis, lipid metabolism, and glucose homeostasis. It is not FDA-approved and is intended for research use only. |
| Molecular Formula |
C28H49NO6S
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|---|---|
| Molecular Weight |
527.756767988205
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| Exact Mass |
527.328
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| Elemental Analysis |
C, 63.72; H, 9.36; N, 2.65; O, 18.19; S, 6.07
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| CAS # |
863239-61-6
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| Related CAS # |
Tauro-obeticholic acid-d5 sodium
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| PubChem CID |
122201312
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| Appearance |
White to yellow solid powder
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| LogP |
4.3
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
36
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| Complexity |
904
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| Defined Atom Stereocenter Count |
11
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| SMILES |
C[C@]12CC[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@H]1[C@@H]3CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@]3(CC[C@H]21)C
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| InChi Key |
JEZXQTZLWHAKAC-NQGMLVFVSA-N
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| InChi Code |
InChI=1S/C28H49NO6S/c1-5-19-23-16-18(30)10-12-28(23,4)22-11-13-27(3)20(7-8-21(27)25(22)26(19)32)17(2)6-9-24(31)29-14-15-36(33,34)35/h17-23,25-26,30,32H,5-16H2,1-4H3,(H,29,31)(H,33,34,35)/t17-,18-,19-,20-,21+,22+,23+,25+,26-,27-,28-/m1/s1
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| Chemical Name |
2-[[(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-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
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| Synonyms |
Tauro-Obeticholic acid; Tauro-Obeticholic acid; 863239-61-6; 6-Etcdca; Obeticholic acid metabolite UPF-1443; T5IG4XE90K; UNII-T5IG4XE90K; Ethanesulfonic acid,2-[[(3a,5b,6a,7a)-6-ethyl-3,7-dihydroxy-24-oxocholan-24-yl]amino]-; 2-[[(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-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; Tauro Obeticholic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8948 mL | 9.4740 mL | 18.9480 mL | |
| 5 mM | 0.3790 mL | 1.8948 mL | 3.7896 mL | |
| 10 mM | 0.1895 mL | 0.9474 mL | 1.8948 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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