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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H43NO5
Molecular Weight 449.6243
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URSODEOXYCHOLYLGLYCINE

SMILES

C[C@]([H])(CCC(=NCC(=O)O)O)[C@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([H])(CC[C@]12C)[C@@]4(C)CC[C@]([H])(C[C@@]4([H])C[C@]3([H])O)O

InChI

InChIKey=GHCZAUBVMUEKKP-XROMFQGDSA-N
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H43NO5
Molecular Weight 449.6243
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
pH-Solubility relations of chenodeoxycholic and ursodeoxycholic acids: physical-chemical basis for dissimilar solution and membrane phenomena.
1980 Jan
Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro.
1994 Sep
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
1998 Jan
Whole-cell response characteristics of ciliated and microvillous olfactory receptor neurons to amino acids, pheromone candidates and urine in rainbow trout.
2001 Nov
Interactions of combined bile acids on hepatocyte viability: cytoprotection or synergism.
2002 Feb 7
High-performance liquid chromatographic mass spectrometric method for the determination of ursodeoxycholic acid and its glycine and taurine conjugates in human plasma.
2003 Dec 25
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.
2003 Oct
Ursodeoxycholic acid inhibits endothelin-1 production in human vascular endothelial cells.
2004 Nov 28
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Uptake of ursodeoxycholate and its conjugates by human hepatocytes: role of Na(+)-taurocholate cotransporting polypeptide (NTCP), organic anion transporting polypeptide (OATP) 1B1 (OATP-C), and oatp1B3 (OATP8).
2006 Jan-Feb
Human multidrug resistance protein 2 transports the therapeutic bile salt tauroursodeoxycholate.
2007 Feb
p53 is a key molecular target of ursodeoxycholic acid in regulating apoptosis.
2007 Nov 23
Glycoursodeoxycholic acid and interleukin-10 modulate the reactivity of rat cortical astrocytes to unconjugated bilirubin.
2007 Sep
Combination of ursodeoxycholic acid and glucocorticoids upregulates the AE2 alternate promoter in human liver cells.
2008 Feb
Determination of bile acids in human serum by on-line restricted access material-ultra high-performance liquid chromatography-mass spectrometry.
2008 Jun 15
Bilirubin injury to neurons: contribution of oxidative stress and rescue by glycoursodeoxycholic acid.
2008 Mar
Contribution of inflammatory processes to nerve cell toxicity by bilirubin and efficacy of potential therapeutic agents.
2009
Effect of SLCO1B1 polymorphism on the plasma concentrations of bile acids and bile acid synthesis marker in humans.
2009 Jun
Protective effects of glycoursodeoxycholic acid in Barrett's esophagus cells.
2010 Feb
Bilirubin selectively inhibits cytochrome c oxidase activity and induces apoptosis in immature cortical neurons: assessment of the protective effects of glycoursodeoxycholic acid.
2010 Jan
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:47:25 UTC 2021
Edited
by admin
on Sat Jun 26 12:47:25 UTC 2021
Record UNII
PF1G5J2X2A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
URSODEOXYCHOLYLGLYCINE
Common Name English
3.ALPHA.,7.BETA.-DIHYDROXY-5.BETA.-CHOLANOYLGLYCINE
Systematic Name English
N-((3.ALPHA.,5.BETA.,7.BETA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)GLYCINE
Systematic Name English
GLYCOURSODEOXYCHOLIC ACID
Common Name English
N-(3.ALPHA.,7.BETA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)GLYCINE
Systematic Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,7.BETA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)-
Systematic Name English
GLYCYLURSODEOXYCHOLIC ACID
Common Name English
URSODEOXYCHOLYLGLYCINE, (+)-
Common Name English
Code System Code Type Description
PUBCHEM
12310288
Created by admin on Sat Jun 26 12:47:26 UTC 2021 , Edited by admin on Sat Jun 26 12:47:26 UTC 2021
PRIMARY
FDA UNII
PF1G5J2X2A
Created by admin on Sat Jun 26 12:47:26 UTC 2021 , Edited by admin on Sat Jun 26 12:47:26 UTC 2021
PRIMARY
CAS
64480-66-6
Created by admin on Sat Jun 26 12:47:26 UTC 2021 , Edited by admin on Sat Jun 26 12:47:26 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
Unit: percent of total bile acids; Daily dose of UDCA: 1g (n=3); Duration: 2 weeks
IN-VIVO
FECAL
METABOLITE TOXIC -> PARENT
IN-VIVO
FECAL
METABOLITE -> PARENT
LCA-sulfate in serum of gallstone patients given UDCA (n=7; 750mg/day [250mg in the morning, 500mg in the evening] for 2 to 3 weeks); Control (n=5): 0.1 micromole/L
IN-VIVO
PLASMA
PARENT -> METABOLITE
MAJOR
PLASMA
METABOLITE ACTIVE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: micromole/24hr (baseline: 0.12 mcmol/24hr); Excretion of LCA-sulfate on day 10 of daily oral administration of 750mg UDCA to healthy volunteers
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: micromole/g creatinine; LCA-sulfate in urine of gallstone patients given UDCA (n=6; 750mg/day [250mg in the morning, 500mg in the evening] for 2 to 3 weeks); Control (n=6): 0.4 micromole/g creatinine
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VIVO
FECAL
METABOLITE TOXIC -> PARENT
IN-VIVO
FECAL
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE TOXIC -> PARENT
IN-VIVO
FECAL
METABOLITE -> PARENT
Unit: percent of total bile acids; Daily dose of UDCA: 15mg/kg (n=6); Duration: 15 days; before treatment (7-KLCA in feces): 1 % of total bile acids
IN-VIVO
FECAL