General
Preferred name
ursodeoxycholic acid
Synonyms
URSODIOL ()
UDCS ()
Urosiol ()
Ursodeoxycholic acid, UDCA ()
Ursodeoxycholic Acid (sodium salt) ()
Ursodeoxycholic Acid-d4 ()
Ursodeoxycholic Acid MaxSpec® Standard ()
Ursodeoxycholic Acid-d4 MaxSpec® Standard ()
Ursofalk ()
Ursogal ()
Ursodeoxycholate ()
Urdox ()
Ursodesoxycholic Acid ()
Ursonorm ()
Actigall ()
Urso 250 ()
NSC-683769 ()
Destolit ()
Urso Forte ()
Cholurso ()
P&D ID
PD002830
CAS
128-13-2
108609-27-4
2898-95-5
347841-46-7
Tags
natural product
drug
available
Approved by
FDA
First approval
1987
Drug indication
Primary biliary cirrhosis
Anticholelithogenic
Drug Status
investigational
approved
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Ursodiol (commonly known as ursodeoxycholic acid) is a product of metabolism of bacteria in the intestine. It is considered a secondary bile acid. The other type of bile acid, primary bile acids, are produced hepatically and subsequently stored in the gallbladder. When primary bile acids are secreted into the large intestine, they can be broken down into secondary bile acids by bacteria present in the intestine. Both types of bile acids assist in the metabolism of dietary fat. Ursodeoxycholic acid regulates cholesterol levels by slowing the rate at which the intestine is able to absorb cholesterol and also acts to break down micelles, which contain cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.
MOA
Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells.; The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution.; ; ;
INDICATION
The drug decreases the absorption of cholesterol and is used to dissolve (cholesterol) gallstones in patients as an alternative to a surgical procedure to remove the gallstones.
DESCRIPTION
Ursodeoxycholic acid (UDCA) acts as an antagonist of the bile acid receptor farnesoid X receptor (FXR) .
SARS-CoV-2 and COVID-19: ACE2's presence on host cells confers susceptibility to SARS-CoV-2 infection. UDCA attenuates bile acid-induced, FXR-mediated upregulation of ACE2 expression in vitro and in vivo . For this effect, UDCA has been proposed as a repurposing drug with antiviral potential against SARS-CoV-2. It is hypothesised that UDCA would reduce SARS-CoV-2 infection potential by lowering the number of ACE2 binding sites on relevant tissues. In support of this theory, a correlation between UDCA treatment for liver conditions and a lower risk of developing severe COVID-19 has been identified,
Ursodeoxycholic acid is found in large quantities in bear bile and this results in the practice of 'farming' bears for bile extraction, in some countries. (GtoPdb)
SARS-CoV-2 and COVID-19: ACE2's presence on host cells confers susceptibility to SARS-CoV-2 infection. UDCA attenuates bile acid-induced, FXR-mediated upregulation of ACE2 expression in vitro and in vivo . For this effect, UDCA has been proposed as a repurposing drug with antiviral potential against SARS-CoV-2. It is hypothesised that UDCA would reduce SARS-CoV-2 infection potential by lowering the number of ACE2 binding sites on relevant tissues. In support of this theory, a correlation between UDCA treatment for liver conditions and a lower risk of developing severe COVID-19 has been identified,
Ursodeoxycholic acid is found in large quantities in bear bile and this results in the practice of 'farming' bears for bile extraction, in some countries. (GtoPdb)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
22
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Enamine BioReference Compounds
EUbOPEN Chemogenomics Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
72
Molecular Weight
392.29
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
3
Rotatable Bonds
4
Ring Count
4
Aromatic Ring Count
0
cLogP
4.48
TPSA
77.76
Fraction CSP3
0.96
Chiral centers
10.0
Largest ring
6.0
QED
0.66
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Membrane Transporter/Ion Channel
Target
Bile salt export pump
AKR1C2, NR1H4
FXR
Member status
member
MOA
Nuclear Factor, Erythroid Derived 2, Like 2 (Nrf2) Activators
Antioxidants
AKR1C3 inhibitor
nuclear factor erythroid derived, like (NRF2) activator
Indication
gallstones
Therapeutic Class
Cholagogues and Choleretics
Recommended Cell Concentration
None
Source data
