Ursodeoxycholic acid/high quality CAS NO.128-13-2

Product Name: Ursodeoxycholic acid

Synonyms: Ursodeoxycholic Acid for System Suitabil;Adursal;Ursic acid;34784-46-7;rsodeoxycholic acid;Porcine deoxycholic acid;Chenodeoxycholic Acid Impurity 1;Ursodeoxycholic acid Manufacturer

CAS: 128-13-2

MF: C24H40O4

MW: 392.57

EINECS: 204-879-3

Product Categories: -;API;Herb extract;DEPACON;BPC;Inhibitors;Bile Acids;Biochemistry;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;API's

Mol File: 128-13-2.mol

Ursodeoxycholic acid Structure

Ursodeoxycholic acid Chemical Properties

Melting point 203-204 °C(lit.)

alpha 60 º (c=2, EtOH)

Boiling point 437.26°C (rough estimate)

density 0.9985 (rough estimate)

refractive index 60.5 ° (C=2, EtOH)

Fp 9℃

storage temp. Refrigerator

solubility ethanol: 50 mg/mL, clear

form Solution

pka pKa 5.04±0.04(H2O t = 25.0±0.1 I = 0.00)(Approximate)

color Clear colorless

Water Solubility practically insoluble

Merck 14,9889

BRN 3219888

InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N

CAS DataBase Reference 128-13-2(CAS DataBase Reference)

Safety Information

Hazard Codes Xi

Risk Statements 36/37/38

Safety Statements 24/25-36-26

RIDADR UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 2

RTECS FZ2000000

F 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)

MSDS Information

Provider Language

3alpha,7beta-Dihydroxy-6beta-cholan-24-oic acid English

ACROS English

SigmaAldrich English

ALFA English

Ursodeoxycholic acid Usage And Synthesis

Choleretic drugs Choleretic drugs are generally divided into two major categories: Choleretic agents and liquid-increase Choleretic agent. The former refers to the drug can promote the secretion of bile. The latter one refers only to those drugs which can increase capacity without increasing bile. The most commonly used Choleretic drugs is mainly cholic acid class-based such as sodium dehydroepiandrosterone acid, chenodeoxycholic acid and ursodeoxycholic acid and so on.

Ursodeoxycholic acid is a chemical agent of natural bile acid which is isolated from the bile of bear. It is the stereo-isomer of chenodeoxycholic acid. It has a similar litholysis effect, efficacy as chenodeoxycholic acid. However, it has a short course of treatment and a small dose. It is bound with taurine in the bile in vivo, and is a hydrophilic bile acids as well as a dissolving agent of cholesterol. It can reduce the secretion of cholesterol in the liver, lower the saturation content of cholesterol in bile, promote the secretion of bile acids, and increase the solubility of cholesterol in the bile so that cholesterol gallstones can be dissolved or prevented. Moreover, it can increase the secretion amount of bile, and have a choleretic effect by relaxing the bile duct mouth sphincter which smoothen the discharge of calculus. This product, however, cannot dissolve other types of gallstones. Ursodeoxycholic acid is useful in the treatment of cholesterol stones, hyperlipidemia, bile secretion disorders, primary biliary cirrhosis, chronic hepatitis, bile reflux gastritis and prevention of liver allograft rejection and reaction. The calculus-dissolving effect of this product is slightly weaker than the CDCA.

Pharmacological effects Ursodeoxycholic acid, namely 3α, 7 β-dihydroxy bile acid, is the 7β-hydroxy epimer of chenodeoxycholic acid. Because of this small structural difference, the product is hydrophilic. It can reduce the activity of the rate-limiting enzyme in cholesterol synthesis in the liver--β-hydroxyl-β-methylglutaryl coenzyme A (HMG-CoA) reductase, thus inhibiting the cholesterol synthesis. It also forms a stable liquid crystalline suspension with cholesterol, and thus unsaturated the bile cholesterol, thereby promoting the separation and dissolution of cholesterol stone. This product can also inhibit the intestinal absorption of cholesterol. Ursodeoxycholic acid can also antagonize the cytotoxic effects of endogenous hydrophobic bile acids, protecting the liver cell membrane. By reducing the overexpression of the main membrane tissue compatibility antigen MHC-1, it can inhibit the production of interleukin-2,4, tumor necrosis factor and interferon α; and increasing the body's levels of interleukin-10,12; It also directly binds to the glucocorticoid receptor, playing a role in immune regulation. In addition, Ursodeoxycholic acid can also inhibit apoptosis, inhibit inflammation, scavenge free radical and have antioxidant effects. After oral administration, it is absorbed through non-ionic passive diffusion in the jejunum, and through active transport in the ileum. The effect of first-pass is large, 50% to 75% of the orally administrated dose is uptake by liver. It is mainly distributed in the liver, intestines and blood plasma, and has a 96% to 99% plasma protein binding rate. Ursodeoxycholic acid concentration in the bile exhibit dose-dependent increase; upon a dose of 20~30mg/(kg d), its concentration in bile is over 60%, reaching the best therapeutic effect. It binds to glycine, taurine in the liver, and is metabolized by intestinal. A small part of metabolite product is excreted from by urine, mostly by the fecal excretion. Biological half-life of oral administration is 3.5 to 5.8 days.

The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chenodeoxycholic acid Chenodeoxycholic acid is white needles-like, mp 119 °C, almost insoluble in water, soluble in methanol and ethanol. This product is a gallstone dissolving agent which have dissolving effect on radiative and transparent cholesterol stones in functional gallbladder. By inhibiting the activity of hepatic β-hydroxy-β-methylglutaryl coenzyme A reductase, blocking the cholesterol biosynthesis, reducing the ratio of bile cholesterol to cholic acid, lowering the saturation of cholesterol, so that the stones will be dissolved for prevention the formation of new stones. In the bile of cholesterol gallstone patients, the ratio of chenodeoxycholic acid over other bile acid significantly decreases. The main metabolite of CDCA is lithocholic acid whose 3-sulfate vinegar conjugates secreted from bile to the intestines will be no longer reabsorbed. It can also be partially converted back to ursodeoxycholic acid through dehydrogenation of the 7-keto lithocholic acid.

For clinically treatment of cholelithiasis using chenodeoxycholic acid, use a daily dose of 15mg/kg. Long-term continuously oral administration has effect on dissolving gallstone or reducing its volume. It is especially suitable for treating high levels of cholesterol in gallstones, with diameter 1~2cm, smooth surface, and transparent cholelithiasis through X-ray. The gallstones of some patients relapse after stopping using. In addition, there are reports that this product can reduce triglyceride and cholesterol for patients of high blood serum. Adverse reactions include diarrhea and elevated level of serum transaminase

Henan CoreyChem Co., Ltd, based on the original Zhengzhou Cote Chemical Research Institute, be brave in absorbing highly educated talents & overseas returnees; actively responded to Zhengzhou City High-tech Zone Government’s Special Care Policy, reorganized and founded in National University of Science and Technology Park, which is a high-tech, stock enterprise of high-end chemical Custom synthesis;The park was created by the People's Government of Henan Province, and proved by Ministry of Education and the National Science & Technology, taking the construction mode of "many college a park, and common development", mainly depends on Zhengzhou University and Henan University’s scientific research and talent advantage to set up Universities, scientific research institute and enterprise scientific research achievements transformation platform, to make high-tech enterprises incubate,  is the new high-tech talent gathering base, high and new technology industry enterprise radiation base, colleges and universities technological innovation base.

 

Henan Coreychem Co., Ltd, facing global High-tech pharmaceutical raw materials, high complex new type intermediates, fine chemicals custom synthesis, scale-up production and Rare chemicals trade. Corey have well-equipped machine, strong technical force and considerate marketing team service. We also have rich experience advantage in basic research, small scale process development, scale-up, industrial technology development & production and cost control.

 

Our R&D center building area is 811 square meters, with 3 contributing proffesor of technical advisor, 4 Dr., 10 masters, and 28 research staff. Our level of chemical synthesis is known to the industry. So we have accumulated rich experience in synthetic methods design and exploring the synthesis of new technology. Not only we are good in heterocyclic chemistry, chiral chemistry (asymmetric synthesis and enzyme reactions), metal organic synthesis, high throughput chemistry, also specializes in bioorganic chemistry, including nucleosides, nucleotides, sugar chemistry, peptide chemistry. R & D center has many sets of 10 liters, 20 liters, 50 liters, 100L multifunction high and low pressure reaction still, rotary evaporator, anhydrous anaerobic reaction devices, hydrogenation equipment, cryogenic process (-120 degrees) equipment, to complete mg level custom synthesis and kg level process development experiments. The Existing 600M NMR, LCMS, Fourier Infrared Spectrometer, liquid chromatography, differentialscanning calorimetry, and other advanced detection equipment areto ensure quality and efficient completion of R&D projects. So far our completed custom synthesis products is more than 5300 species, where dozens of them are non-CAS declaration products, almost including all types of organic reactions.

 

At present, in addition to our headquarters in Zhengzhou, we also have another product base in Jun County, Henan Province. This base is the attracting investment of science and technology project of Jun County govenment’s, which covers 6529 square meters. In addition to bear our own company’s 1000L-5000L pilot task, also bear the function of Henan pilot incubation service platform, In order to improve Henan and surroundings’ synthetic reaction pilot service ability and the key technology development capabilities. Base with three GMP standards workshop, a testing center, one test center,one experiment center and associatd supporting facilities, can carry out oxidation, hydrogenation (70 kg pressure), halogenated, acieration, etherification, condensation, cyclization, formatting, ammoniated, diazotization andpilot service such as azide reactions etc. In the future we will work hard to make it become the most complete production system in central China and even the whole country, the highest technical level, the strongest talent team, the most popular service scope of pilot incubation service platform.

 

Henan Coreychem co., LTD. is committed to provide cost effective chemical service to the global fine chemical industry product development agencies; we adhering to the consistent good commercial reputation, to create a highly efficient, high quality of chemical research, development, production, sales and service of integrated platform, let our customers faster, better get ideal and thoughtful service.