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A4438

Sigma-Aldrich

p-Acetamidophenyl β-D-glucuronide sodium salt

>98% (TLC)

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Synonym(s):
Acetaminophen glucuronide, Paracetamol glucuronide
Linear Formula:
C14H16NO8Na
CAS Number:
120595-80-4
Molecular Weight:
349.27
MDL number:
MFCD00153898
UNSPSC Code:
12352201
PubChem Substance ID:
24890866
NACRES:
NA.25

Quality Level

200

Assay

>98% (TLC)

form

powder

impurities

<6% water (Karl Fischer)

color

white to off-white

solubility

water: 25 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

[Na+].CC(=O)Nc1ccc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C([O-])=O)cc1

InChI

1S/C14H17NO8.Na/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21;/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21);/q;+1/p-1/t9-,10-,11+,12-,14+;/m0./s1

InChI key

OINXIJJEOMGKPB-CYRSAHDMSA-M

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Application

Acetaminophen glucuronide (AA-Gluc) is used as a reference material in procedures that analyse urine and plasma for acetaminophen metabolites to indicate hepatotoxicity.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T Andrew Clayton et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(34), 14728-14733 (2009-08-12)
We provide a demonstration in humans of the principle of pharmacometabonomics by showing a clear connection between an individual's metabolic phenotype, in the form of a predose urinary metabolite profile, and the metabolic fate of a standard dose of the
Scott A Reisman et al.
Toxicological sciences : an official journal of the Society of Toxicology, 109(1), 31-40 (2009-02-28)
Acetaminophen (AA) is a widely used antipyretic drug that causes hepatotoxicity at high doses. Nuclear factor erythroid 2-related factor 2 (Nrf2) is a transcription factor that mitigates electrophilic stress from AA by inducing genes, such as NAD(P)H:quinone oxidoreductase 1 (Nqo1)
Mayu Kakehi et al.
Toxicological sciences : an official journal of the Society of Toxicology, 147(2), 360-369 (2015-07-17)
There are various interspecies differences in xenobiotic-metabolizing enzymes. It is known that cats show slow glucuronidation of drugs such as acetaminophen and strong side effects due to the UGT1A6 pseudogene. Recently, the UGT1A6 pseudogene was found in the Northern elephant
Andrew Rowland et al.
Drug metabolism and disposition: the biological fate of chemicals, 43(1), 147-153 (2014-11-09)
This study characterized the kinetics, variability, and factors that affect UDP-glucuronic acid (UDP-GlcUA) uptake by human liver microsomes (HLM). Biphasic kinetics were observed for UDP-GlcUA uptake by HLM. Uptake affinities (assessed as Kd) of the high- and low-affinity components differed
Yanli Zhao et al.
British journal of clinical pharmacology, 80(5), 1076-1085 (2015-03-27)
The antiviral agent favipiravir is likely to be co-prescribed with acetaminophen (paracetamol). The present study evaluated the possiblility of a pharmacokinetic interaction between favipiravir and acetaminophen, in vitro and in vivo. The effect of favipivir on the transformation of acetaminophen
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