Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H40O4 |
Molecular Weight | 392.572 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=RUDATBOHQWOJDD-UZVSRGJWSA-N
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
Molecular Formula | C24H40O4 |
Molecular Weight | 392.572 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1a3a8942-94d4-4292-bf74-0a67d92acb90#section-11.1Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01586
Sources: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1a3a8942-94d4-4292-bf74-0a67d92acb90#section-11.1
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01586
Ursodiol tablets, USP are bile acids indicated for the treatment of patients with primary biliary cirrhosis. Ursodiol (Ursodeoxycholic acid), a naturally occurring hydrophilic bile acid, derived from cholesterol, is present as a minor fraction of the total human bile acid pool. 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. In addition to the replacement and displacement of toxic bile acids, other mechanisms of action include cytoprotection of the injured bile duct epithelial cells (cholangiocytes) against toxic effects of bile acids, inhibition of apotosis of hepatocytes, immunomodulatory effects, and stimulation of bile secretion by hepatocytes and cholangiocytes. Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2047 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=22223860 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | URSODIOL Approved UseUrsodiol Launch Date1989 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.2 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22414767 |
15 mg/kg bw 1 times / day multiple, oral dose: 15 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
URSODIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
49.8 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22414767 |
15 mg/kg bw 1 times / day multiple, oral dose: 15 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
URSODIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 50 mg/kg, 3 times / day Route: oral Route: multiple Dose: 50 mg/kg, 3 times / day Sources: |
unhealthy, 37-65 |
|
500 mg 2 times / day multiple, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea (1.7%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1.7% Disc. AE |
500 mg 2 times / day multiple, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Inhibition 20 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/16678547/ |
yes | no (co-administration study) Comment: UDCA did not lead to detectable changes in midazolam pharmacokinetics Sources: https://pubmed.ncbi.nlm.nih.gov/16678547/ |
||
Sources: https://pubmed.ncbi.nlm.nih.gov/16678547/ |
yes | weak (co-administration study) Comment: UDCA modestly decreased digoxin disposition without Sources: https://pubmed.ncbi.nlm.nih.gov/16678547/ |
PubMed
Title | Date | PubMed |
---|---|---|
The chemopreventive role of ursodeoxycholic acid in azoxymethane-treated rats: suppressive effects on enhanced group II phospholipase A2 expression in colonic tissue. | 1998 Dec 25 |
|
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury. | 1999 Aug |
|
Ursodeoxycholic acid protects hepatocytes against oxidative injury via induction of antioxidants. | 1999 Sep 24 |
|
Genotoxic polycyclic aromatic hydrocarbon ortho-quinones generated by aldo-keto reductases induce CYP1A1 via nuclear translocation of the aryl hydrocarbon receptor. | 2000 Feb 15 |
|
Ursodeoxycholic acid (UDCA) for the treatment of amoxycillin-clavulanate potassium (Augmentin)-induced intra-hepatic cholestasis: report of two cases. | 2000 Mar |
|
Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid. | 2001 |
|
Treatment of nonalcoholic fatty liver: present and emerging therapies. | 2001 |
|
[Experience in treatment of chronic toxic hepatitis by ursodeoxicholic acid]. | 2001 |
|
Primary sclerosing cholangitis. | 2001 Apr |
|
Prevention of colon cancer with ursodiol in ulcerative colitis. | 2001 Aug |
|
Stimulation of ATP secretion in the liver by therapeutic bile acids. | 2001 Aug 15 |
|
Micronuclei induction, cell cycle delay and apoptosis as markers of cellular stress caused by ursodeoxycholic acid in human lymphocytes. | 2001 Aug 22 |
|
Crystal structure of human type III 3alpha-hydroxysteroid dehydrogenase/bile acid binding protein complexed with NADP(+) and ursodeoxycholate. | 2001 Aug 28 |
|
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon. | 2001 Aug 28 |
|
Functional modulation of the glucocorticoid receptor and suppression of NF-kappaB-dependent transcription by ursodeoxycholic acid. | 2001 Dec 14 |
|
Ursodeooxycholic acid for primary biliary cirrhosis. | 2001 Feb |
|
Changes in titers of antimitochondrial and antinuclear antibodies during the course of primary biliary cirrhosis. | 2001 Feb |
|
Management of drug-induced liver disease. | 2001 Feb |
|
Ursodeoxycholic acid complexation with 2-hydroxypropyl-beta-cyclodextrin increases ursodeoxycholic acid biliary excretion after single oral administration in rats. | 2001 Feb |
|
Clinical studies with silymarin: fibrosis progression is the end point. | 2001 Feb |
|
Novel bile acid derivatives induce apoptosis via a p53-independent pathway in human breast carcinoma cells. | 2001 Feb 10 |
|
Long-term evaluation of extracorporeal shock-wave lithotripsy for cholesterol gallstones. | 2001 Jan |
|
Use of ursodeoxycholic acid in liver diseases. | 2001 Jan |
|
Chemoprevention in ulcerative colitis: narrowing the gap between clinical practice and research. | 2001 Jan 16 |
|
Ursodiol use is associated with lower prevalence of colonic neoplasia in patients with ulcerative colitis and primary sclerosing cholangitis. | 2001 Jan 16 |
|
Ursodeoxycholic acid 'mechanisms of action and clinical use in hepatobiliary disorders'. | 2001 Jul |
|
Prevention and treatment of veno-occlusive disease. | 2001 Jul-Aug |
|
Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradation. | 2001 Jun |
|
Low in vivo toxicity of a novel cisplatin-ursodeoxycholic derivative (Bamet-UD2) with enhanced cytostatic activity versus liver tumors. | 2001 Jun |
|
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid. | 2001 Mar |
|
Treatment of cholestasis and cholestatic disorders. | 2001 Mar |
|
Characterization of primary pure cholesterol hepatolithiasis: cholangioscopic and selective cholangiographic findings. | 2001 Mar |
|
Ursodeoxycholic acid administration in patients with cholestasis of pregnancy: effects on primary bile acids in babies and mothers. | 2001 Mar |
|
Hepatitis C virus infection with peripheral neuropathy is not always associated with cryoglobulinaemia. | 2001 Mar |
|
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases. | 2001 May |
|
Synthetic bile acid derivatives induce nonapoptotic death of human retinal pigment epithelial cells. | 2001 May |
|
MDR3 gene defect in adults with symptomatic intrahepatic and gallbladder cholesterol cholelithiasis. | 2001 May |
|
A preliminary trial of high-dose ursodeoxycholic acid in primary sclerosing cholangitis. | 2001 Oct |
|
Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. | 2001 Oct 19 |
|
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. | 2001 Oct 19 |
|
Apolipoprotein E polymorphism, a marker of disease severity in primary biliary cirrhosis? | 2001 Sep |
|
Biliary excretion of tauroursodeoxycholate-3-sulfate in the rat. | 2001 Sep |
Substance Class |
Chemical
Created
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admin
on
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Mon Mar 31 17:46:37 GMT 2025
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on
Mon Mar 31 17:46:37 GMT 2025
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Record UNII |
724L30Y2QR
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000006801
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FDA ORPHAN DRUG |
242607
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FDA ORPHAN DRUG |
55390
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LOINC |
55159-8
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FDA ORPHAN DRUG |
191204
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NDF-RT |
N0000175802
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WHO-VATC |
QA05AA02
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FDA ORPHAN DRUG |
22187
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EU-Orphan Drug |
EU/3/17/1878
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FDA ORPHAN DRUG |
636718
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NCI_THESAURUS |
C2089
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LIVERTOX |
NBK548309
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WHO-ATC |
A05AA02
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NCI_THESAURUS |
C29703
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Code System | Code | Type | Description | ||
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Ursodiol
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PRIMARY | |||
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31401
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PRIMARY | |||
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204-879-3
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PRIMARY | |||
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100000092107
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PRIMARY | |||
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CHEMBL1551
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PRIMARY | |||
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DTXSID6023731
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PRIMARY | |||
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683769
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PRIMARY | |||
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SUB11389MIG
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PRIMARY | |||
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D014580
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PRIMARY | |||
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724L30Y2QR
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PRIMARY | |||
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128-13-2
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PRIMARY | |||
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62427
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ALTERNATIVE | |||
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m11344
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PRIMARY | Merck Index | ||
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78604
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PRIMARY | |||
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C1818
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PRIMARY | |||
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1707806
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724L30Y2QR
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PRIMARY | |||
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DB01586
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7104
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Z-35
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9907
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2797
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4920
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11065
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URSODIOL
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA
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PARENT -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
BILE
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METABOLITE -> PARENT |
BILE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |