| Identification | More | [Name]
Chenodeoxycholic acid | [CAS]
474-25-9 | [Synonyms]
3ALPHA,7ALPHA-DIHYDROXY-5BETA-CHOLANIC ACID
5B-CHOLANIC ACID-3A,7A-DIOL
5BETA-CHOLANIC ACID-3,7-DIOL
5BETA-CHOLANIC ACID-3ALPHA,7ALPHA-DIOL
CDCA
CHENODEOXYCHOLIC ACID
CHENODESOXYCHOLIC ACID
CHENODIOL
CHOLAN-24-OIC ACID, 3,7-DIHYDROXY-, (3A,5B,7A)-
DEOXYCHENOCHOLIC ACID
URSODEOXYCHOLOC ACID
3,7-dihydroxy-,(3-alpha,5-beta,7-alpha)-cholan-24-oicaci
3,7-dihydroxy-,(3alpha,5beta,7alpha)-cholan-24-oicaci
3,7-Dihydroxy-5-Cholanicacid
3-alpha,7-alpha-dihydroxy-5-beta-cholan-24-oicaci
3-alpha,7-alpha-dihydroxy-5-beta-cholan-24-oicacid
3-alpha,7-alpha-dihydroxycholanicacid
3-alpha,7-alpha-dihydroxycholansaeure
7-alpha-hydroxylithocholicacid
anthropodeoxycholicacid | [EINECS(EC#)]
207-481-8 | [Molecular Formula]
C24H40O4 | [MDL Number]
MFCD00064142 | [Molecular Weight]
392.57 | [MOL File]
474-25-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
165-167 °C (lit.) | [alpha ]
12 º (c=1, CHCl3) | [Boiling point ]
437.26°C (rough estimate) | [density ]
0.9985 (rough estimate) | [refractive index ]
1.4460 (estimate) | [Fp ]
9℃ | [storage temp. ]
room temp | [solubility ]
PRACTICALLY INSOLUBLE | [form ]
Powder | [pka]
pKa 4.34 (Uncertain) | [color ]
White to off-white | [Water Solubility ]
PRACTICALLY INSOLUBLE | [Usage]
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. Fcilitates fat absorptio | [Detection Methods]
Optical Rotatory Dispersion | [Merck ]
13,2062 | [BRN ]
3219887 | [InChIKey]
RUDATBOHQWOJDD-BSWAIDMHSA-N | [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. | [LogP]
3.05 at 20℃ | [CAS DataBase Reference]
474-25-9(CAS DataBase Reference) | [EPA Substance Registry System]
474-25-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R63:Possible risk of harm to the unborn child. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
2
| [RTECS ]
FZ1980000
| [HS Code ]
29181990 |
| Hazard Information | Back Directory | [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) | [Definition]
ChEBI: Chenodeoxycholic acid is a dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of a chenodeoxycholate. | [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.] |
| Questions And Answer | Back Directory | [Uses]
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.
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