Ursodiol

Names

[ CAS No. ]:
128-13-2

[ Name ]:
Ursodiol

[Synonym ]:
(3a,5b,7b,8x)-3,7-dihydroxycholan-24-oic acid
Ursofalk
17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,7b-diol
3α,7β-Dihydroxy-6β-cholan-24-oic acid
Ursolvan
Ursochol
Peptarom
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Actigall
Delursan
Ursodeoxycholic acid
(3α,5β,7β)-3,7-Dihydroxycholan-24-oic acid
3a,7b-dihydroxy-5b-cholan-24-oic acid
(3α,5β,7β,8ξ,20R)-3,7-Dihydroxycholan-24-oic acid
Cholan-24-oic acid, 3,7-dihydroxy-, (3α,5β,7β)-
Litursol
Cholit-ursan
(3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid
3,7-Dihydroxycholan-24-oic acid
3α,7β-dihydroxy-5β-cholan-24-oic acid
(3a,5b,7b)-3,7-Dihydroxycholan-24-oic Acid
cholan-24-oic acid, 3,7-dihydroxy-, (3a,5b,7b,8x)-
Ursacol
Ursodiol
Cholan-24-oic acid, 3,7-dihydroxy-, (3α,5β,7β,8ξ,20R)-
3a,7b-Dioxycholanic Acid
Destolit
MFCD00003680
3alpha,7beta-Dihydroxy-6beta-cholan-24-oic acid
Arsacol
EINECS 204-879-3

Biological Activity

[Description]:

Ursodiol reduces cholesterol absorption and is used to dissolve gallstones.Target: OthersUrsodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery. The drug is very expensive, however, and if the patient stops taking it, the gallstones tend to recur if the condition that gave rise to their formation does not change. For these reasons, it has not supplanted surgical treatment by cholecystectomy.Ursodeoxycholic acid is currently the only established drug for the treatment of chronic cholestatic liver diseases. It has cytoprotective, anti-apoptotic, membrane stabilizing, anti-oxidative and immunomodulatory effects. Prolonged administration of ursodeoxycholic acid in patients with primary biliary cirrhosis (PBC) is associated with survival benefit and a delaying of liver transplantation.

[Related Catalog]:

Natural Products >> Steroids

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. Jackson H, et al. Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study. Hepatology. 2007 Oct;46(4):1131-7.

[2]. Kumar D, et al. Use of ursodeoxycholic acid in liver diseases. J Gastroenterol Hepatol. 2001 Jan;16(1):3-14.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
547.1±25.0 °C at 760 mmHg

[ Melting Point ]:
203-206 ºC

[ Molecular Formula ]:
C₂₄H₄₀O₄

[ Molecular Weight ]:
392.572

[ Flash Point ]:
298.8±19.7 °C

[ Exact Mass ]:
392.292664

[ PSA ]:
77.76000

[ LogP ]:
4.66

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.543

[ Storage condition ]:
2~8°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
FZ2000000

Synthetic Route

Click to get detail synthetic route

Preparation

Articles

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

[Preventive administration of new UDCA derivatives in experimental alcoholic steatohepatitis].

Eksp. Klin. Farmakol. 76(1) , 25-9, (2013)

We have studied the prophylactic effect of new derivatives of ursodeoxycholic acid (UDCA), including UDCA-N-acetylcysteine, UDCA-L-acetylcysteine, and nor-UDCA (in doses equivalent to 40 mg/kg of UDCA...