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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
Structure of URSODIOL

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

HIDE SMILES / InChI

Description

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

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
URSODIOL
Primary
Chenodiol
PubMed

PubMed

TitleDatePubMed
Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor.
2002 Jul 19
The amino acid residues asparagine 354 and isoleucine 372 of human farnesoid X receptor confer the receptor with high sensitivity to chenodeoxycholate.
2002 Jul 19
Differences in the regulation of the classical and the alternative pathway for bile acid synthesis in human liver. No coordinate regulation of CYP7A1 and CYP27A1.
2002 Jul 26
Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling.
2002 Jul 5
Two novel mutations in the sterol 27-hydroxylase gene causing cerebrotendinous xanthomatosis.
2002 Mar
The UDCA dosage deficit: a fate shared with CDCA.
2002 Mar
[Treatment of cholestatic liver diseases].
2002 Mar 15
Relationship between asymptomatic hypercholanaemia of pregnancy and progesterone metabolism.
2002 May
A novel primary bile acid in the Shoebill stork and herons and its phylogenetic significance.
2002 May
A natural product that lowers cholesterol as an antagonist ligand for FXR.
2002 May 31
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose range for Chenodiol is 13 to 16 mg/kg/day in two divided doses, morning and night, starting with 250 mg b.i.d. the first two weeks and increasing by 250 mg/day each week thereafter until the recommended or maximum tolerated dose is reached. If diarrhea occurs during dosage buildup or later in treatment, it usually can be controlled by temporary dosage adjustment until symptoms abate, after which the previous dosage usually is tolerated. Dosage less than 10 mg/kg usually is ineffective and may be associated with increased risk of cholecystectomy, so is not recommended.
Route of Administration: Oral
In Vitro Use Guide
Hepatocytes were treated with Chenodiol at 10, 30, and 100 uM for 48 h, and RNA was extracted for real-time PCR analysis. Chenodiol markedly suppressed CYP7A1, the rate-limiting enzyme of bile acid synthesis, but only moderately (35%) down-regulated CYP8B1 at a high concentration of 100uM. Chenodiol increased the two major target genes of the farnesoid X receptor (FXR), namely the small heterodimer partner (SHP) by fourfold, and markedly induced fibroblast growth factor 19 (FGF19) over 100-fold.
Name Type Language
URSODIOL
INCI   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
INCI   USAN  
Official Name English
URSODEOXYCHOLIC ACID [MART.]
Common Name English
URSODEOXYCHOLIC ACID [EP]
Common Name English
NSC-683769
Code English
URSOCHOL
Common Name English
URSODIOL [MI]
Common Name English
3.ALPHA.,7.BETA.-DIHYDROXY-5B-CHOLAN-24-OIC ACID
Common Name English
URSODEOXYCHOLIC ACID [WHO-DD]
Common Name English
URSODIOL [USP]
Common Name English
URSODIOL [USAN]
Common Name English
URSODIOL [INCI]
Common Name English
URSO
Brand Name English
URSODESOXYCHOLIC ACID
Common Name English
URSODIOL [ORANGE BOOK]
Common Name English
ACTIGALL
Common Name English
UDCA
Common Name English
URSODIOL [VANDF]
Common Name English
URSODEOXYCHOLIC ACID
EP   INN   MART.   WHO-DD  
INN  
Official Name English
URSODEOXYCHOLIC ACID [INN]
Common Name English
CHOLAN-24-OIC ACID, 3,7-DIHYDROXY-, (3.ALPHA.,5.BETA.,7.BETA.)-
Common Name English
URSODIOL [USP-RS]
Common Name English
URSODEOXYCHOLATE
Common Name English
Classification Tree Code System Code
NDF-RT N0000006801
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
FDA ORPHAN DRUG 242607
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
FDA ORPHAN DRUG 55390
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
FDA ORPHAN DRUG 191204
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
NDF-RT N0000175802
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
WHO-VATC QA05AA02
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
FDA ORPHAN DRUG 22187
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
EU-Orphan Drug EU/3/17/1878
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
FDA ORPHAN DRUG 636718
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
NCI_THESAURUS C2089
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
LIVERTOX 1011
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
WHO-ATC A05AA02
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
NCI_THESAURUS C29703
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
Code System Code Type Description
PUBCHEM
31401
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-879-3
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
ChEMBL
CHEMBL1551
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
EPA CompTox
128-13-2
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
EVMPD
SUB11389MIG
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
MESH
D014580
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
CAS
128-13-2
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
RXCUI
62427
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
ALTERNATIVE
MERCK INDEX
M11344
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY Merck Index
LactMed
128-13-2
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
NCI_THESAURUS
C1818
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
DRUG BANK
DB01586
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
IUPHAR
7104
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
INN
4920
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
RXCUI
11065
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY
WIKIPEDIA
URSODIOL
Created by admin on Mon Oct 21 20:48:48 UTC 2019 , Edited by admin on Mon Oct 21 20:48:48 UTC 2019
PRIMARY