474-25-9 Usage
Uses
Different sources of media describe the Uses of 474-25-9 differently. You can refer to the following data:
1. Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol. henodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX). It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies.
2. Chenodeoxycholic acid is a bile acid that induces apoptosis through protein kinase C signaling pathways.It is a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion.Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress. Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis.
Chenodeoxycholic acid is widely utilized in therapeutic applications. It is applied in medical therapy to dissolve gallstones. It is employed in the treatment of cerebrotendineous xanthomatosis. It is used to treat constipation and cerebrotendineous xanthomatosis. It acts as a urea receptor in supramolecular chemistry which can contain anions. It is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for dye solar cells.
Chenodeoxycholic Acid is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for Dye Solar Cells. This co-adsorbent will prevent dye aggregation on the semiconductor surface, reducing losses in the solar cell's operation.
Chenodeoxycholic Acid is a white solid added with the dye powder to the solvent while preparing staining solutions. The concentration of co-adsorbent is typically 10 fold the dye concentration.
Chenodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX).
It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies.
Chenodeoxycholic acid (CDCA) is a hydrophobic primary bile acid that activates nuclear receptors involved in cholesterol metabolism.EC50 concentrations for activation of FXR range from 13-34 μM.In cells, CDCA also binds to bile acid binding proteins (BABP) with a reported stoichiometry of 1:2.CDCA toxicity is linked to increased cellular glutathione levels and increased oxidative stress. Exposure of cells to excess CDCA contributes to liver and intestinal cancers.
3. A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus fa
cilitates its excretion. Fcilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol.
4. An apoptosis inducer via PKC-dependent signalling pathway.
Description
Chenodeoxycholic acid is the first agent to be introduced into the US market for the treatment of radiolucent gallstones. Large scale clinical trials have demonstrated the safety and efficacy of this agent. Chenodeoxycholic acid reduces the biliary concentration of cholesterol relative to that of bile acids and phospholipid, reducing the saturation and thus the lithogenicity of the bile. Success rates in dissolving gallstones are in the range of 50-70% within 4-24 months of treatment. Continuation of the drug after stone dissolution may be required to prevent reoccurrence. Chenodeoxycholic acid is the 7α-isomer of ursodeoxycholic acid which was introduced into the European market in 1978.
chenodeoxycholic acid structure
Chemical Properties
Off-White Solid
Originator
Rowell (USA)
History
Chenodeoxycholic acid was isolated in 1924 from goose gall by Adolf Windaus and human gall by Heinrich Wieland.Its complete structural configuation was elucidated by Hans Lettre at the University of Gottingen.
In 1968, William Admirand and Donald Small at Boston University Medical School established that in patients with gallstones their bile was saturated with cholesterol, sometimes even exhibiting microcrystals, whereas this was not the case in normal people.It was then found that biliary levels of cholic acid and chenodeoxycholic acid were lower in patients with cholesterol gallstones than in normal people. Leslie Thistle and John Schoenfield at the Mayo Clinic in Rochester, Minnesota, then administered individual bile salts by mouth for four months and found that chenodeoxycholic acid reduced the amount of cholesterol in the bile.This led to a national collaborative study in the United States, which confirmed the effectiveness of chenodeoxycholic acid in bringing about dissolution of gallstones in selected patients. However, recent developments such as laparoscopic cholecystectomy and endoscopic biliary techniques have curtailed the role of chenodeoxycholic acid and ursodeoxycholic acid in the treatment of cholelithiasis.
Manufacturing Process
To 1,400 ml of an approximately 50% water/triglycol solution of the
potassium salt of chenodeoxycholic acid, obtained by the Wolff-Kishner
reduction (using hydrazine hydrate and potassium hydroxide) from 50 g of 7-
acetyl-12-ketochenodeoxycholic acid, 220 ml of dilute hydrochloric acid is
added to bring the pH to 2. The solution is stirred and the crude
chenodeoxycholic acid precipitates. The precipitate is recovered and dried to
constant weight at about 60°C. About 36 g of the crude chenodeoxycholic
acid, melting in the range of 126°-129°C, is obtained.
25 g of crude chenodeoxycholic acid so obtained is dissolved in 750 ml of
acetonitrile while stirring and heating. 3 g of activated charcoal is added and
then removed by suction filtering. The resulting liquid filtrate is cooled, the
pure chenodeoxycholic acid crystallizing out. The crystals are recovered by
suction filtering and the recovered crystals dried under vacuum. The yield is
19 g of pure chenodeoxycholic acid with a melting range of 168°-171°C.
Brand name
CHEWM
Therapeutic Function
Gallostone dissolving agent
World Health Organization (WHO)
Chenodeoxycholic acid was introduced in 1975 for the treatment
of cholelithiasis. It is available in several countries and the World Health
Organization is not aware that registration has been refused in any other country.
General Description
Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol.
Flammability and Explosibility
Nonflammable
Purification Methods
This major bile acid in vertebrates (~80mg) is chromatographed on silica gel (5g) and eluted with CHCl3/EtOAc (3:2) and crystallised from EtOAc/hexane. It has IR: max 1705 cm-1(CHCl3). It also crystallises from EtOAc, EtOAc/heptane after purifying via the poorly soluble Na and K salt if necessary. [Kametani et al. J Org Chem 4 7 2331 1982, Beilstein 10 IV 1604.]
Check Digit Verification of cas no
The CAS Registry Mumber 474-25-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 4 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 474-25:
(5*4)+(4*7)+(3*4)+(2*2)+(1*5)=69
69 % 10 = 9
So 474-25-9 is a valid CAS Registry Number.
InChI:InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22?,23+,24-/m1/s1
474-25-9Relevant articles and documents
Solvolysis of chenodeoxycholic acid sulfates
Cohen,Budai,Javitt
, p. 621 - 626 (1981)
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Preparation method and application of seal cholic acid
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, (2021/02/10)
The invention provides a method for selectively separating seal cholic acid from a duck bile extract, which facilitates the utilization of the seal cholic acid which is an important biological resource in the duck bile. The invention also provides a method for preparing chenodeoxycholic acid from the seal cholic acid. Therefore, the problem of insufficient supply of chenodeoxycholic acid raw materials can be alleviated, improved. and meanwhile, corresponding biological waste pollution is also avoided. The method is easy for industrial production and has very good economic value and applicationprospect.
Method for preparing chenodeoxycholic acid from seal cholic acid
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Paragraph 0039; 0049-0053; 0063-0066, (2021/02/10)
The invention provides a method for preparing chenodeoxycholic acid CDCA by taking seal cholic acid as a raw material, on one hand, an application is found for seal cholic acid, and on the other hand,a new raw material source is provided for chenodeoxycholic acid, so that the problem of supply shortage of chenodeoxycholic acid crude drugs can be partially relieved, meanwhile, the problem of corresponding biological waste pollution is avoided, the problem of industrial production is well solved, and the method has very good economic value and application prospect.
Method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid
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Paragraph 0013, (2021/02/06)
The invention belongs to the field of organic synthesis of carbocyclic compounds, and particularly relates to a method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid. According to the method, chenodeoxycholic acid with purity of 97.6% is synthesized by using duck cholic acid as a raw material. The comprehensive yield is 87.8%, the purity of the product is highwhile a high-temperature reaction is avoided, and later impurity removal is simple and convenient.
