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Chenodesoxycholsure

Chenodeoxycholic acid

HCID 5702181
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Grundinformationen

CAS
474-25-9
Standard-SMILES
C[C@H](CCC(=O)O)[C@H]1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O
Summenformel
C24H40O4
Durchschnittliche Molmasse
392,57 g/mol

Namen und Bezeichner

Bevorzugter Name
Chenodeoxycholic acid
Lokaler Name
Chenodesoxycholsure
Englischer Name
Chenodeoxycholic acid
Summenformel
C24H40O4
Molmasse
392.57

Namen und Synonyme

CDCACHENODIOLCHENODEOXYCHOLATE3ALPHA,7ALPHA-DIHYDROXY-5BETA-CHOLANIC ACIDChenixChenodeoxychoLURSODEOXYCHOLOC ACID3a,7a-Dihydroxy-5b-cholanoic acid(R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidFluibil

Datenbank-Bezeichner

CAS
474-25-9
PubChem CID
5702181
ChEMBL
CHEMBL101089

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
165 · 165-167 °C (lit.)
Siedepunkt
437.26 °C · 437.26°C (rough estimate)
Dichte
0.9985 · 0.9985 (rough estimate)
Brechungsindex
1.446 · 1.4460 (estimate)
Flammpunkt
9 ℃ · 9℃
storage temp.
room temp
Löslichkeit
PRACTICALLY INSOLUBLE
pka
4.34 · pKa 4.34 (Uncertain)
Aggregatzustand
Powder
Farbe
White to off-white
Wasserlöslichkeit
PRACTICALLY INSOLUBLE
Merck
13 · 13,2062
BRN
3219887 · 3219887
Major Application
pharmaceutical (small molecule)
InChIKey
RUDATBOHQWOJDD-BSWAIDMHSA-N
SMILES
C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
LogP
3.05 at · 3.05 at 20℃
CAS Datenbank
474 · 474-25-9(CAS DataBase Reference)
EPA chemische Informationen
Chenodiol (474-25-9)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
2
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29181990
RTECS-Nr.
FZ1980000
risk_code
63
hazard_code
Xn
safety_code
22-24/25-45-36/37
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungChenodeoxycholic 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

HistoryChenodeoxycholic 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.

VerwendenA 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.

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Vorgelagerte Rohstoffe

NatriumcholatEthanolHydrochloric acid alcoholBariumchloridNatriumcarbonatHydrazine hydrateKaliumhydroxid

Nachgelagerte Produkte

UrsodeoxycholsuresqualamineChenodeoxycholic acid sodiumTaurochenodeoxycholic acid sodium saltGlycochenodeoxycholic acid sodium salt

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