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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
Ursodeoxycholic acid inhibits endothelin-1 production in human vascular endothelial cells.
2004 Nov 28
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
p53 is a key molecular target of ursodeoxycholic acid in regulating apoptosis.
2007 Nov 23
Combination of ursodeoxycholic acid and glucocorticoids upregulates the AE2 alternate promoter in human liver cells.
2008 Feb
Contribution of inflammatory processes to nerve cell toxicity by bilirubin and efficacy of potential therapeutic agents.
2009
Protective effects of glycoursodeoxycholic acid in Barrett's esophagus cells.
2010 Feb
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