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Isodeoxycholic acid is a bile acid that is formed via epimerization of deoxycholic acid by intestinal bacteria. As a bile acid, it interacts with various nuclear receptors and membrane receptors involved in bile acid signaling, including the farnesoid X receptor (FXR) and the G-protein coupled bile acid receptor (TGR5). Through these receptors, isodeoxycholic acid regulates gene expression involved in bile acid synthesis, lipid metabolism, and glucose homeostasis. The compound has a greater critical micelle concentration than deoxycholic acid (DCA), indicating reduced detergent activity, and is less active than DCA in certain biological assays. This reduced detergent activity may contribute to a more favorable safety profile compared to more hydrophobic bile acids. Isodeoxycholic acid has effects on choleresis (bile flow stimulation) and liver biochemistry. Its structural similarity to UDCA allows comparative evaluation of epimer-specific activity and potential therapeutic applications. As an endogenous metabolite, it is generated through the epimerization of deoxycholic acid by intestinal bacteria and is primarily found in feces as saponifiable conjugates with long-chain fatty acids. Its role in bile acid metabolism makes it a useful tool for studying cholestasis models and liver function modulation.
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| ln Vitro |
In vitro, isodeoxycholic acid has notable effects on choleresis and liver biochemistry. It has a greater critical micelle concentration than deoxycholic acid (DCA), indicating reduced detergent activity, and is less active than DCA in certain biological assays. The compound is used in hepatobiliary research to study bile acid metabolism, cholestasis models, and liver function modulation. In cell-based assays, isodeoxycholic acid is studied for its effects on hepatocyte function, bile acid transport, and gene expression. Its structural similarity to UDCA allows comparative evaluation of epimer-specific activity. In studies of bile acid signaling, isodeoxycholic acid is used to investigate the activation of nuclear receptors such as FXR and TGR5. The compound's effects on cell viability, apoptosis, and inflammation are assessed in hepatocyte and intestinal cell cultures. As a secondary bile acid, isodeoxycholic acid is also studied for its role in intestinal physiology and its interactions with the gut microbiota. Its reduced detergent activity compared to DCA suggests that it may have a more favorable profile for therapeutic applications.
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| ln Vivo |
In vivo, isodeoxycholic acid has effects on choleresis and liver biochemistry. As a bile acid, it undergoes enterohepatic circulation and plays a role in the regulation of intestinal physiology. The compound is studied for its role in bile acid metabolism, cholestasis models, and liver function modulation. In animal models of cholestasis, isodeoxycholic acid is administered to assess its effects on bile flow, liver enzyme levels, and histopathological changes. Its structural similarity to UDCA allows comparative evaluation of epimer-specific activity and potential therapeutic applications. Isodeoxycholic acid is generated through the epimerization of deoxycholic acid by intestinal bacteria and is primarily found in feces as saponifiable conjugates with long-chain fatty acids. In vivo studies have investigated the compound's effects on cholesterol metabolism, bile acid synthesis, and enterohepatic circulation. Its reduced detergent activity compared to DCA suggests that it may have a more favorable safety profile for therapeutic applications. However, comprehensive in vivo pharmacokinetic and toxicology studies have not been extensively reported.
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| Enzyme Assay |
In vitro enzyme and receptor binding assays for isodeoxycholic acid typically involve the use of isolated nuclear receptors such as FXR or membrane receptors such as TGR5. For FXR binding assays, the receptor is incubated with radiolabeled or fluorescently labeled bile acid ligands in the presence of varying concentrations of isodeoxycholic acid. The binding affinity (IC₅₀ or Ki) is determined from competitive binding curves. For TGR5 binding assays, membrane preparations from cells expressing TGR5 are used, and the activation of the receptor is measured by monitoring downstream signaling pathways such as cAMP production. For studies of bile acid transport, membrane vesicles or polarized cell monolayers are used to measure the transport of isodeoxycholic acid by bile acid transporters such as the apical sodium-dependent bile acid transporter (ASBT) or the organic anion transporting polypeptides (OATPs). The compound's critical micelle concentration is measured by surface tension or fluorescence methods. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems (pH 7.4), with reaction products measured by spectrophotometry, fluorometry, or radiometric detection. The compound's structural similarity to UDCA allows comparative evaluation of epimer-specific activity.
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| Cell Assay |
In vitro cell-based assays for isodeoxycholic acid are performed using hepatocyte or intestinal cell cultures. Primary human hepatocytes or hepatocyte cell lines (e.g., HepG2, HuH-7) are cultured in appropriate medium and treated with isodeoxycholic acid at various concentrations (typically 1-100 μM) for 24-72 hours. Following treatment, cells are harvested, and various endpoints are measured, including bile acid transporter expression (by qPCR or western blotting), bile acid synthesis gene expression, cell viability (by MTT or LDH assays), and markers of apoptosis and inflammation. For intestinal cell studies, Caco-2 cells are used to study the effects of isodeoxycholic acid on intestinal barrier function and bile acid transport. Each experiment includes appropriate controls (untreated cells, vehicle controls, and positive controls such as UDCA or DCA) and is performed in triplicate to ensure statistical reliability. The compound is typically dissolved in DMSO as a stock solution and diluted in culture medium to the desired final concentration, with the final DMSO concentration kept below 0.1% to avoid solvent effects. Cell viability is routinely monitored to ensure that observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo animal experiments with isodeoxycholic acid are conducted in mouse or rat models of cholestasis or bile acid metabolism disorders. Typically, 8-12 week old male or female rodents are used, and the compound is administered via oral gavage or intraperitoneal injection at doses ranging from 10-100 mg/kg. In cholestasis models, bile duct ligation or administration of cholestatic agents (e.g., alpha-naphthylisothiocyanate) is used to induce cholestasis. Following isodeoxycholic acid administration, bile flow is measured by bile duct cannulation, and blood samples are collected to measure liver enzyme levels (ALT, AST, ALP), bilirubin, and bile acid levels. Liver tissue is collected for histopathological examination and gene expression analysis. For studies of enterohepatic circulation, radiolabeled or deuterated isodeoxycholic acid is administered, and its appearance in bile, plasma, and feces is measured over time. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=6-10 per group) to ensure statistical power. The compound is formulated for administration using appropriate vehicles such as saline or DMSO/PEG mixtures, in which it is soluble. Endpoints include bile flow, liver enzyme levels, histopathological scores, and gene expression changes.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of isodeoxycholic acid are characteristic of bile acids, which undergo enterohepatic circulation. Following oral administration, the compound is absorbed in the intestine and transported to the liver via the portal circulation. In the liver, bile acids are taken up by hepatocytes and secreted into bile. They are then stored in the gallbladder and released into the intestine during digestion. In the intestine, bile acids are reabsorbed and returned to the liver, completing the enterohepatic circulation. The compound's pharmacokinetics are influenced by its structure, with the 3β-hydroxyl configuration affecting its solubility, transport, and metabolism. Isodeoxycholic acid has a greater critical micelle concentration than deoxycholic acid (DCA), indicating reduced detergent activity, which may affect its solubility and membrane interactions. The compound is primarily found in feces as saponifiable conjugates with long-chain fatty acids. Its elimination half-life is determined by the rate of enterohepatic circulation and renal excretion. As with all bile acids, the pharmacokinetics of isodeoxycholic acid can be influenced by liver function, intestinal transit time, and the gut microbiota.
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| Toxicity/Toxicokinetics |
The toxicological profile of isodeoxycholic acid is related to its properties as a bile acid. Bile acids can be toxic at high concentrations due to their detergent activity, which can disrupt cell membranes and cause cell death. However, isodeoxycholic acid has a greater critical micelle concentration than deoxycholic acid (DCA), indicating reduced detergent activity. This reduced detergent activity suggests that isodeoxycholic acid may have a more favorable safety profile compared to more hydrophobic bile acids. In cell-based assays, isodeoxycholic acid has been shown to be less active than DCA in certain biological assays. In animal studies, the compound has been administered at doses that affect choleresis and liver biochemistry without reported overt toxicity. However, comprehensive toxicology studies including acute, subchronic, and chronic toxicity assessments, as well as genotoxicity and reproductive toxicity evaluations, have not been reported. The compound is classified as a research chemical and is not approved for human use. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment. As with all chemicals, ingestion, inhalation, and skin contact should be avoided.
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| References | |
| Additional Infomation |
Isodeoxycholic acid is a choline compound.
Isodeoxycholic acid is a valuable research tool for studying bile acid metabolism, cholestasis models, and liver function modulation. It is an endogenous metabolite and a 3β-hydroxylated secondary bile acid. The compound is generated through the epimerization of deoxycholic acid by intestinal bacteria and is primarily found in feces as saponifiable conjugates with long-chain fatty acids. It is the 3β-epimer of ursodeoxycholic acid (UDCA) and has notable effects on choleresis and liver biochemistry. The compound has a greater critical micelle concentration than DCA, indicating reduced detergent activity, and is less active than DCA in certain biological assays. Its structural similarity to UDCA allows comparative evaluation of epimer-specific activity and potential therapeutic applications. Isodeoxycholic acid is not approved for any clinical indication and is strictly for research use only. Its role in bile acid metabolism makes it a useful tool for studying cholestasis, liver function, and the interactions between bile acids and the gut microbiota. |
| Molecular Formula |
C24H40O4
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|---|---|
| Molecular Weight |
392.57
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| Exact Mass |
392.293
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| CAS # |
566-17-6
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| PubChem CID |
164672
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| Appearance |
White to off-white solid powder
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| Density |
1.128 g/cm3
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| Boiling Point |
547.1ºC at 760 mmHg
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| Melting Point |
210°C (lit.)
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| Flash Point |
298.8ºC
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| Index of Refraction |
1.543
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| LogP |
4.477
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
28
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| Complexity |
605
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| Defined Atom Stereocenter Count |
10
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| SMILES |
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCCC4)C)O)O)C
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| InChi Key |
ZHCAAZIHTDCFJX-QLEQUTGBSA-N
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| InChi Code |
InChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
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| Chemical Name |
(4R)-4-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-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]pentanoic 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 |
| 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) |
DMSO: 100 mg/mL (254.73 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.37 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5473 mL | 12.7366 mL | 25.4732 mL | |
| 5 mM | 0.5095 mL | 2.5473 mL | 5.0946 mL | |
| 10 mM | 0.2547 mL | 1.2737 mL | 2.5473 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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