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06863

Sigma-Aldrich

Glycoursodeoxycholic acid

≥96.0% (TLC)

Synonym(s):

N-(3α,7β-Dihydroxy-5β-cholan-24-oyl)glycine, N-[(3α,5β,7β)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine, GUDCA, Glycylursodeoxycholic acid, Ursodeoxycholylglycine

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About This Item

Empirical Formula (Hill Notation):
C26H43NO5
CAS Number:
64480-66-6
Molecular Weight:
449.62
MDL number:
MFCD00137427
UNSPSC Code:
12161900
PubChem Substance ID:
329748294
NACRES:
NA.25

biological source

synthetic

assay

≥96.0% (TLC)

form

powder

functional group

carboxylic acid

SMILES string

[H][C@@]12[C@]([C@](CC[C@@H](O)C3)(C)[C@]3([H])C[C@@H]2O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCC(NCC(O)=O)=O

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

InChI key

GHCZAUBVMUEKKP-XROMFQGDSA-N

Related Categories

Application


  • Glycoursodeoxycholic Acid Alleviates Arterial Thrombosis via Suppressing Diacylglycerol Kinases Activity in Platelet.: Highlights the therapeutic potential of Glycoursodeoxycholic acid in alleviating arterial thrombosis by inhibiting diacylglycerol kinase activity in platelets (Yang et al., 2024).

Biochem/physiol Actions

Secondary bile acid derived from acyl glycine. Glycoursodeoxycholic Acid (GUDCA) is reported to have cytoprotective and anti-inflammatory effects.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Kazuya Maeda et al.
Molecular pharmaceutics, 3(1), 70-77 (2006-05-12)
Ursodeoxycholate (UDCA) is widely used for the treatment of cholestatic liver disease. After oral administration, UDCA is absorbed, taken up efficiently by hepatocytes, and conjugated mainly with glycine to form glycoursodeoxycholate (GUDC) or partly with taurine to form tauroursodeoxycholate (TUDC)
Sandra L Silva et al.
Neuropharmacology, 62(7), 2398-2408 (2012-03-01)
Neuronal oxidative damage and cell death by unconjugated bilirubin (UCB) showed to be mediated by overstimulation of glutamate receptors and nitric oxide (NO) production, which was abrogated by the bile acid glycoursodeoxycholic acid (GUDCA). Microglia, a crucial mediator of CNS
Jingyu Yan et al.
Scientific reports, 7(1), 4211-4211 (2017-06-25)
Cholestasis is a clinical disorder defined as an impairment of bile flow, and that leads to toxic bile acid (BA) accumulation in hepatocytes. Here, we investigated the hepatoprotective effect of Yinchenhaotang (YCHT), a well-known formulae for the treatment of jaundice
A Roda et al.
The Journal of biological chemistry, 258(10), 6362-6370 (1983-05-25)
The relationship between chemical structure and the concentration at which self-association occurs in water or in 0.15 M Na+ ion was examined for more than 50 bile salts and bile salt analogues varying in substituents on the steroid nucleus or
A Roda et al.
Pharmaceutical research, 11(5), 642-647 (1994-05-01)
A new enteric-coated formulation of sodium ursodeoxycholate was prepared and administered to man. The barrier film disintegrates and releases the drug only at pH > or = 5.5. The sodium salt of glycoursodeoxycholate was also prepared and encapsulated like ursodeoxycholate.
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