128-13-2
Ursodeoxycholic acid
CAS: 128-13-2
Molecular Formula: C24H40O4
128-13-2 - Names and Identifiers
128-13-2 - Physico-chemical Properties
| Molecular Formula | C24H40O4 |
| Molar Mass | 392.57 |
| Density | 0.9985 (rough estimate) |
| Melting Point | 203-204 °C (lit.) |
| Boling Point | 437.26°C (rough estimate) |
| Specific Rotation(α) | 60 º (c=2, EtOH) |
| Flash Point | 9℃ |
| Water Solubility | practically insoluble |
| Solubility | Soluble in ethanol and glacial acetic acid, dissolved in sodium hydroxide test solution, insoluble in chloroform. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White powder |
| Color | White - almost white. |
| Merck | 14,9889 |
| BRN | 3219888 |
| pKa | pKa 5.04±0.04(H2Ot = 25.0±0.1I = 0.00)(Approximate) |
| Storage Condition | 2-8°C |
| Refractive Index | 60.5 ° (C=2, EtOH) |
| MDL | MFCD00003680 |
| Physical and Chemical Properties | This product is white powder; Odorless, bitter taste. Mp 200-204 °c. Soluble in ethanol and acetic acid, soluble in sodium hydroxide solution, insoluble in chloroform. UDCA is the isomer of CDCA, its litholytic effect is stronger than CDCA, no Diarrhea and liver toxicity. UDCA can reduce the absorption of cholesterol, and can reduce the synthesis of cholesterol and cholesterol content in bile. In addition, UDCA can also reduce concanavalin A binding fragment, which can promote the formation of bile crystals, thereby inhibiting the formation of stones. The combined use of UDCA and CDCA can enhance the litholytic effect of each alone, while reducing side effects. The combination of the two is mainly used for the treatment of gallbladder cholesterol stones. When the density of gallstones and bile or the CT Value of gallstones is less than 75 units, the dissolution rate of UDCA is the fastest. Patients with cholelithiasis after the use of this product, can increase the number of peripheral platelets. |
| Use | Suitable for the prevention and treatment of cholesterol gallstones |
128-13-2 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 2 |
| RTECS | FZ2000000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29181990 |
| Toxicity | LD50 in mice (g/kg): 0.1 i.v. (Ardenne, Reitnauer); in rats, mice (mg/kg): 2000, 6000 s.c.; 1000, 1200 i.p., 310, 260 i.v. (Ward) |
128-13-2 - Reference
| Reference Show more | 1. Cao Yan, Song Qingqing, Li Jun, et al. Analysis of Bile Acids in Yak Gallbladder [J]. Chinese Journal of Traditional Chinese Medicine, Volume 44, Issue 12, 2019, pp. 2538-2543, MEDLINE ISTIC PKU CSCD CA BP, 2019. 2. Li Wei, Jiang Zhenzhen, Li Han, Tu Pengfei, Song Qingqing, Yu Juan, Song Yuelin. On-line pressurized solvent extraction-ultra performance liquid chromatography-ion trap-time of flight-mass spectrometry was used to qualitatively analyze the chemical grouping of Pien Tze Huang [J]. Chromatography, 2021,39(05):478-487. 3. Cao Yan, Li Ting, Chang Anqi, Jiang Zhenzhen, Yu Juan, Tu Pengfei, Song Yuelin. Analysis of Bile Acids in Snake Gallbladder [J]. Chinese journal of traditional Chinese medicine, 2021,46(01):130-138. 4. [IF = 1.627] Yanming Xia et al."Transport mechanism of ursodeoxycholic acid in human placental BeWo cells." Biopharm Drug Dispos. 2018 Jul;39(7):335-343 5. [IF = 5.396] Shiming Huang et al."A sulfated polysaccharide from Gracilaria Lemaneiformis regulates cholesterol and bile acid metabolism in high-fat diet mICE." Food Funct. 2019 Jun;10(6):3224-3236 6. [IF = 5.396] Cong Liang et al."Lactiplantibacillus plantarum H-87 prevents high-fat diet-induced obesity by regulating bile acid metabolism in C57BL/6J mice." Food Funct.2021 May;12(10):4315-4324 7. [IF = 3] Qu Lala et al."Phenotypic assessment and screening of ETA/ETB receptors with label-free dynamic mass redistribution say." N-S Arch Pharmacol. 2020 Jun;393(6):937-950 8. [IF = 5.396] Juan Wu et al."Sargassum fusiforme polysaccharide is a potential auxiliary substance for metformin in the management of diabetes." Food Funct. 2022 Feb;: 9. [IF = 6.558] Yan Cao et al."Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid." ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 |
128-13-2 - Nature
Open Data Verified Data
This product is white powder; Odorless, bitter. This product is soluble in ethanol, insoluble in chloroform; Soluble in glacial acetic acid, dissolved in sodium hydroxide solution. The melting point was 200-204 °c. Ursodeoxycholic acid is a unique component of bear bile. It is isomeric with Chenodeoxycholic acid, but less toxic than Chenodeoxycholic acid, less dosage. After oral administration, the product was rapidly absorbed; There were two peak plasma concentrations at th and 3H, respectively. Biological Half-Life of 3.5~3.8 days. UDCA in the liver with glycine or taurine rapid binding, from the bile into the small intestine, to participate in enterohepatic circulation, small intestine combined with UDCA-partial hydrolysis back to free type; the other part is converted to LCA by the action of bacteria, which in turn is sulfated, thereby reducing its potential hepatotoxicity. It can dissolve gallstones, inhibit blood cholesterol deposition, liver, gallbladder, detoxification and other effects. Its sodium salt is stronger than other bile acids in promoting liver glycogen storage, fatty acid hydrolysis and hypoglycemic effect.
Last Update：2024-01-02 23:10:35
128-13-2 - Use
Open Data Verified Data
- gallstone dissolving drug.
- usage and dosage: oral, cholagogic, 50mg once, mg once daily; Cholelithiasis, 450-mg once daily, 2 times.
Last Update：2022-01-01 11:14:04
128-13-2 - Safety
Open Data Verified Data
- in the bile acid drugs, this product is the weakest hemolytic effect, the lowest toxicity, the least side effects, almost no deoxycholic acid, Chenodeoxycholic acid Diarrhea and liver toxicity side effects. Pregnant women, severe hepatitis and biliary obstruction, severe hepatitis disabled.
- light-shielding storage, closed storage.
Last Update：2022-01-01 11:14:04
128-13-2 - Reference Information
| LogP | 3-3.38 at 20℃ |
| choleretic drugs | choleretic drugs can generally be divided into choleretic drugs and liquid-increasing choleretic drugs. The former refers to drugs that can promote bile secretion, and the latter refers to drugs that only increase bile volume but do not increase bile components. At present, the commonly used choleretic drugs are mainly cholic acids. There are sodium cholate, dehydrocholic acid, chenodeoxycholic acid and ursodeoxycholic acid. Ursodeoxycholic acid is a chemical preparation of natural bile acid separated from bear bile. It is an epimoisomer of chenodeoxycholic acid. Its stone-dissolving effect and curative effect are similar to chenodeoxycholic acid, but the course of treatment is short and the dose is small. In the body, it is combined with taurine and exists in bile. It is a hydrophilic bile acid and a cholesterol stone dissolving agent. It can reduce the secretion of cholesterol by the liver, reduce the saturation of cholesterol in bile, promote the secretion of bile acids, increase the solubility of cholesterol in bile, dissolve cholesterol stones or prevent the formation of stones. It can increase the amount of bile secretion, relax the sphincter of the bile duct to produce choleretic effect, which is beneficial to the discharge of stones. This product cannot dissolve other types of gallstones. Ursodeoxycholic acid is suitable for the treatment of cholesterol stones, hyperlipidemia, bile secretion disorders, primary biliary cirrhosis, chronic hepatitis, bile reflux gastritis and prevention of acute rejection and reaction of liver transplantation. The litholytic effect of this product is slightly weaker than that of chenodeoxycholic acid. |
| pharmacological action | ursodeoxycholic acid is 3α,7β-dihydroxycholanoic acid, which is the 7β-hydroxy epimomer of chenodeoxycholic acid. it is this slight difference in structure that makes this product hydrophilic. This product can reduce the activity of the rate-limiting enzyme of cholesterol synthesis in the liver-β-hydroxy-β-methylglutaryl coenzyme A(HMG-CoA) reductase, which inhibits cholesterol synthesis; and forms a stable liquid crystal suspension with cholesterol. The matter makes the cholesterol in the bile unsaturated, and then promotes the precipitation and dissolution of the cholesterol in the stone. This product can also inhibit intestinal absorption of cholesterol. Ursodeoxycholic acid can also antagonize the cytotoxic effect of endogenous hydrophobic bile acids and protect liver cell membranes. This product reduces the overexpression of major histocompatibility antigen MHC-1 of liver cell membrane; inhibits the production of interleukin-2, 4, tumor necrosis factor and interferon α; improves the level of interleukin-10 and 12 in the body; And directly bind to glucocorticoid receptor to play an immunomodulatory role. In addition, ursodeoxycholic acid has the effects of inhibiting cell apoptosis, inhibiting inflammation, clearing free radicals and resisting oxidation. After oral administration, it is mainly absorbed in the upper segment of jejunum by non-ionic passive diffusion and in the ileum by active transport. The first pass effect is large. 50% ~ 75% of the oral dose is absorbed by the liver; it is mainly distributed in liver, intestine and plasma. The binding rate of plasma protein is 96% ~ 99%. The concentration of ursodeoxycholic acid in bile increased in a dose-dependent manner. When the dose is 20~30mg/(kg d), the concentration in bile exceeds 60%, which can achieve the best therapeutic effect. In the liver, it is combined with glycine, taurine, etc., and is metabolized by intestinal bacteria in the colon. A small part of the metabolites are excreted in the urine, and most of them are excreted in the feces. The biological half-life during oral administration is 3.5~5.8 days. |
| chenodeoxycholic acid | chenodeoxycholic acid is a white needle-like crystal with a melting point of 119 ℃, almost insoluble in water, soluble in methanol and ethanol. This product is a gallstone dissolving agent, which has a dissolving effect on radiolucent cholesterol stones in the functional gallbladder. It inhibits liver β-hydroxy β-methylglutaryl coenzyme A reductase, prevents cholesterol biosynthesis, reduces the ratio of cholesterol to cholic acid in bile, reduces cholesterol saturation, dissolves stones, and prevents the formation of new stones. In the bile of patients with cholesterol stones, the ratio of chenodeoxycholic acid to other bile acids decreased significantly. The main metabolite of chenodeoxycholic acid is lithocholic acid. The 3-sulfate conjugate produced by it is secreted from bile to the intestine and is no longer reabsorbed, but excreted from the body. It can also be partially converted to ursodeoxycholic acid by dehydrogenation via 7-ketocholic acid. clinically, chenodeoxycholic acid is used to treat cholelithiasis. 15mg/kg per day, long-term continuous oral administration can dissolve or reduce the volume of gallstones. It is especially suitable for gallstones with high cholesterol content, diameter of 1 ~ 2cm, smooth surface and transparent X-ray irradiation. Some patients recurred and formed gallstones after drug withdrawal. In addition, it has been reported that this product has the effect of reducing serum triglycerides and cholesterol in patients with hyperlipidemia. Adverse reactions include diarrhea and elevated serum transaminase. Figure 1 is the chemical structural formula of chenodeoxycholic acid |
| drug interaction | (1) when combined with chenodeoxycholic acid, the effect of promoting cholesterol content and saturation reduction in bile is greater than that of single medication and the additive effect of the two drugs. (2) this product should not be combined with cholestyramine or acid making agent containing aluminum hydroxide, so as not to affect absorption. (3) Oral contraceptives can affect the efficacy of this product. |
| adverse reactions | is smaller than chenodeoxycholic acid and generally does not cause diarrhea. Constipation, allergy, headache, dizziness, pancreatitis and tachycardia are occasionally seen. |
| precautions | (1) use with caution for elderly patients. (2) Long-term use can increase the number of peripheral platelets. (3) If biliary colic occurs repeatedly in the treatment of cholesterol stones, the symptoms do not improve or even worsen, or obvious stone calcification occurs, the treatment should be suspended and surgery should be performed. (4) This product cannot dissolve bile pigment stones, mixed stones and X-ray-opaque stones. (5) liver function should be checked regularly during taking. |
| TLCS method for determination of ursodeoxycholic acid and chenodeoxycholic acid in bear bile | (1) test article: ursus arctos Linnaeus of bear brown bear or dry bile of black bear Selenarctos thibetanus G.Cuvier. (2) chromatographic conditions: high performance silica gel thin layer plate (Yantai); Isooctane-isopropyl ether-glacial acetic acid-n-butanol-water (6:3:3:1.8:0.6) is the developing agent; 5% sulfuric acid ethanol solution of saturated ammonium bisulfate is used as the color developing agent, sprayed for color development, heated at 110 ℃ for 10min, and inspected the spot position under natural light and 365nm ultraviolet light. (3) preparation of reference substance solution: precisely weigh ursodeoxycholic acid, chenodeoxycholic acid and cholic acid reference substance, dissolve it with methanol and prepare a solution containing 1mg per milliliter as the reference substance solution. (4) preparation of sample solution: accurately weigh 8mg of bear bile, add 1.5ml of 30% sodium hydroxide solution, and hydrolyze in boiling water bath for 10h. Use concentrated hydrochloric acid to adjust pH 1~2, ethyl acetate extraction (10ml × 2 times, 5ml × 2 times), combine the extract, concentrate, and fix the volume in a 2ml volumetric flask as a sample solution. (5) determination: absorb 1μl of sample solution and 1μl and 2μl of reference solution, intersect on the same thin layer plate respectively, expand, take out, dry and develop color according to the above thin layer chromatography conditions. Reflective sawtooth scanning was performed by thin layer scanning method. The excitation wavelength of ursodeoxycholic acid is λex = 380nm, and the emission wavelength is λem = 450nm. λem = 470nm,λex = 550nm for chenodeoxycholic acid and cholic acid. Measure the integrated value of the absorption of the sample and the reference substance, and calculate it. (6) chromatogram fig. 2 is the thin layer chromatogram of bear bile by TLCS method. remarks: 1. natural bear bile; 2. bear bile powder; 3. bear gallstones; 4. reference substance a. ursodeoxycholic acid; B. chenodeoxycholic acid; (7) determination results fig. 3 shows the content table of ursodeoxycholic acid and chenodeoxycholic acid in bear bile |
| use | gallstone dissolving drug. Mainly used for cholesterol gallstones that are not suitable for surgical treatment, especially the gallbladder function is basically normal, the stone diameter is less than 15mm, X-ray, non-calcified floating cholesterol stones have a high cure rate. It also has a certain therapeutic effect on toxic hepatitis, cholecystitis, primary sclerosing cholangitis, and primary cholestatic cirrhosis. To improve the efficacy of interferon alpha in the treatment of chronic hepatitis C. There are diarrhea, rare constipation, allergic reactions, itching, headache, dizziness, stomach pain, pancreatitis and bradycardia. Patients with complete biliary tract obstruction and severe liver dysfunction and pregnant women should not use it. suitable for the prevention and treatment of cholesterol gallstones, anionic detergent anionic detergent, for biochemical research. |
| production method | method 1. preparation of methyl ester 3 α, 7 α-diacetylcholic acid using chenodeoxycholic acid as raw material 36ml of anhydrous methanol, 1g of dried hydrogen chloride gas, 12g of cholic acid, stirring, heating and reflux for 20-30min, leaving at room temperature for several hours, precipitating crystals, freezing, filtering, washing with ether, drying, and obtaining methyl cholic acid. Take 2g of methyl cholate, 9.6ml of benzene, 2.4ml of pyridine, 2.4ml of acetic anhydride, shake for 10-15min, stand at room temperature for 20h, pour the reaction solution into 100ml of water, remove the benzene layer, repeatedly wash with distilled water, recover the solvent, wash the solid residue once with petroleum ether, recrystallize with methanol-aqueous solution to obtain 3 α,7 α-diacetylcholic acid methyl ester. Preparation of cholic acid → cholic acid methyl ester → 3 α,7 α-diacetylcholic acid methyl ester chenodeoxycholic acid 1.5g of diacetylcholic acid methyl ester, 24 ml of acetic acid, potassium chromate solution (0.76g of potassium chromate dissolved in 1.8ml of water), heating to 40 ℃, reacting for 8h, adding 120ml of water, shaking for a moment, placing for 12h, filtering, washing with distilled water to neutral, drying to obtain 3 α,7 α-Diacetoxy-12-ketocholanoate methyl ester, referred to as 12-one. Take 15g of 12-ketone, add 150ml of diethylene glycol ether, add 15ml of 80% hydrazine hydrate solution, add 15g of potassium hydroxide, heat to 30 ℃ for reflux for 15h, heat to 195-200 ℃, reflux for 2.5h, heat to 217 ℃ for reaction for a moment, cool to 190 ℃, add 0.7ml of hydrazine hydrate solution, heat from 215 ℃ to 220 ℃ within 3h, cool, add 600ml of distilled water, add 10% sulfuric acid to adjust pH 3, crystallization is precipitated, filtered, washed to neutral, ethyl acetate is added, the water layer is discarded, the organic layer is washed 1-2 times with water, and distilled under reduced pressure to obtain white 3α, 7α-dihydroxycholanoic acid, namely chenodeoxycholic acid. Preparation of 3 α,7 α-diacetylcholic acid methyl ester → 3 α,7 α-diacetyloxy -12-ketocholine acid methyl ester → 3 α,7 α-dihydroxycholine acid (chenodeoxycholic acid) ursodeoxycholic acid fine product Take 2g of chenodeoxycholic acid, add 100ml of acetic acid, add 20g of potassium acetate, shake and dissolve, add 1.5g of potassium chromate (dissolved in 10ml of water), leave it overnight at room temperature, add 200ml of water, filtration, washing with water, drying to obtain 3α-hydroxy-7-ketocholanoic acid. Take 4g of 3 α-hydroxy -7-ketocholanoic acid, add 100ml of n-butanol, heat to about 115 ℃, add 8g of metal sodium in several times, gradually precipitate white slurry, continue to react for 30min, add 120ml of water, stir to heat up and dissolve transparently, evaporate to remove the organic layer under reduced pressure, add 500ml of water to the residue, dissolve, filter, add 10% sulfuric acid to adjust pH3. white flocculent precipitates, filter, wash with water until neutral and dry, add ethyl acetate to wash and dilute ethanol to crystallize to obtain 3 α,7 β-dihydroxycholanoic acid, namely ursodeoxycholic acid. Chenodeoxycholic acid [potassium chromate] → 3 α-hydroxy-7-ketocholic acid [metal sodium, 115 ℃]→ 3 α, 7 β-dihydroxycholanoic acid (ursodeoxycholic acid) method 2. using pig bile salt or pig bile as raw materials Ursodeoxycholic acid was isolated from pig bile salt or pig bile by thin layer chromatography. Pig bile salt contains free and bound UDCA with a content of about 30%. Pig bile contains bound UDCA with a content of about 0.6%. |
Last Update：2024-04-09 15:16:47
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