Page last updated: 2024-12-07

ursocholic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Ursocholic acid (UDCA) is a bile acid found in the bile of bears. It is a naturally occurring compound that is also produced synthetically. UDCA is used to treat a variety of liver diseases, including primary biliary cholangitis (PBC), primary sclerosing cholangitis (PSC), and cholestatic liver disease. It is also used to dissolve gallstones and prevent the formation of new gallstones. UDCA is thought to work by improving bile flow, protecting liver cells from damage, and reducing inflammation. It has been studied extensively for its therapeutic potential in various liver disorders. UDCA has been shown to reduce the progression of liver disease and improve symptoms in patients with PBC and PSC. It has also been shown to be effective in dissolving gallstones in some patients. UDCA is generally well tolerated, but side effects can occur, including diarrhea, abdominal pain, and elevated liver enzymes. It is important to note that UDCA is not a cure for any liver disease, but it can help to manage symptoms and slow the progression of disease.'

ursocholic acid: see also records for allocholic and cholic acids [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ursocholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID122340
CHEMBL ID1254416
CHEBI ID81240
SCHEMBL ID288612
MeSH IDM0096946

Synonyms (45)

Synonym
ursocholic acid
LMST04010088
3alpha,7beta,12alpha-trihydroxy-5beta-cholan-24-oic acid
7-epicholate
7beta-hydroxyisocholic acid
C17644
3alpha,7beta,12alpha-trihydroxy-5beta-cholanic acid
2955-27-3
7-epicholic acid
(4r)-4-[(3r,5s,7s,8r,9s,10s,12s,13r,14s,17r)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic acid
CHEMBL1254416
chebi:81240 ,
A820339
(4r)-4-[(3r,5s,7s,8r,9s,10s,12s,13r,14s,17r)-10,13-dimethyl-3,7,12-tris(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic acid
mlp1t05rbx ,
cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7beta,12alpha)-
unii-mlp1t05rbx
SCHEMBL288612
ursocholic acid [ep impurity]
3.alpha.,7.beta.,12.alpha.-trihydroxy-5.beta.-cholanic acid
3.alpha.,7.beta.,12.alpha.-trihydroxy-5 beta-cholan-24-oic acid
ursodeoxycholic acid impurity d [ep impurity]
(3alpha,5beta,7beta,12alpha)-3,7,12-trihydroxycholan-24-oic acid
3alpha, 7beta, 12alpha-trihydroxy-5beta-cholanoic acid
BHQCQFFYRZLCQQ-UTLSPDKDSA-N
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid
mfcd25563269
(4r)-4-[(1r,3as,3br,4s,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-1-yl]pentanoic acid
AS-70048
J-017562
3a,7b,12a-trihydroxy-5b-cholanoic acid
3a,7b,12a-trihydroxy-5b-cholan-24-oate
3a,7b,12a-trihydroxy-5b-cholan-24-oic acid
3a,7b,12a-trihydroxycholanic acid
3a,7b,12a-trihydroxy-5b-cholanic acid
3a,7b,12a-trihydroxycholanate
3a,7b,12a-trihydroxy-5b-cholanate
3a,7b,12a-trihydroxy-5b-cholanoate
4-[(5s,7s,8s,10s,13r,17r)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic acid
CS-0059325
HY-113212
Q27155182
DTXSID301018756
V10235
AKOS037646653

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by RMw."( Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
Gilmer, JF; Keaveney, R; Kelleher, D; Long, A; Majer, F; Peta, VK; Sharma, R; Wang, J, 2010
)
0.36

Bioavailability

ExcerptReferenceRelevance
" Ursocholic acid is well absorbed and excreted into bile and transformed into deoxycholic acid by the intestinal microflora in mice."( Differential effects of ursodeoxycholic acid and ursocholic acid on the formation of biliary cholesterol crystals in mice.
Akiyoshi, T; Igimi, H; Ishihara, S; Nomura, Y; Takase, H; Uchida, K, 1991
)
1.45
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human urinary metaboliteAny metabolite (endogenous or exogenous) found in human urine samples.
EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitorAn EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 7alpha-hydroxysteroid dehydrogenase (EC 1.1.1.159).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
bile acidAny member of a group of hydroxy-5beta-cholanic acids occuring in bile, where they are present as the sodium salts of their amides with glycine or taurine. In mammals bile acids almost invariably have 5beta-configuration.
3alpha-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the alpha-position.
12alpha-hydroxy steroid
C24-steroidA steroid compound with a structure based on a 24-carbon (cholane) skeleton.
trihydroxy-5beta-cholanic acid
7beta-hydroxy steroidA 7-hydroxy steroid in which the hydroxy group at position 7 has beta-configuration.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID515398Cytotoxicity against human HET-1A cells assessed as cell viability after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID515400Cytotoxicity against human HET-1A cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID515399Cytotoxicity against human HuH7 cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (40.00)18.7374
1990's11 (31.43)18.2507
2000's7 (20.00)29.6817
2010's3 (8.57)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 90.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index90.90 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index4.19 (4.65)
Search Engine Demand Index157.97 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (90.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (11.11%)5.53%
Reviews1 (2.78%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other31 (86.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]