acetaminophen glucuronide

Names

[ Name ]:
acetaminophen glucuronide

[Synonym ]:
Acetaminophen D-glucuronide
[14C]-Acetaminophen glucuronide
paracetamol glucuronide
acetaminophen glucuronide
acetaminophen O-beta-D-glucosiduronic acid
4-glucuronosido-acetanilide

Biological Activity

[Description]:

Acetaminophen glucuronide (APAP-glu) is an inactive glucuronide metabolite of Acetaminophen (HY-66005)[1][2]. Acetaminophen is a selective cyclooxygenase-2 (COX-2) inhibitor and a potent hepatic N-acetyltransferase 2 (NAT2) inhibitor[3][4].

[Related Catalog]:

Research Areas >> Others

[In Vitro]

Acetaminophen is metabolized in the liver mainly by glucuronidation and sulfation, thus generating the nontoxic metabolites, Acetaminophen glucuronide (APAP-glu). Acetaminophen glucuronide is a substrate for both canalicular Mrp2 and basolateral Mrp3 in rodents[1].

[References]

[1]. Carolina I Ghanem, et al. Shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats. J Pharmacol Exp Ther. 2005 Dec;315(3):987-95.

[2]. Liudmila L Mazaleuskaya, et al. PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.

[3]. Hinz, B, et al. Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J, 2008. 22(2): p. 383-90.

[4]. Rothen JP, et al. Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo. Pharmacogenetics. 1998 Dec;8(6):553-9.

Chemical & Physical Properties

[ Density]:
1.61g/cm3

[ Boiling Point ]:
697.4ºC at 760mmHg

[ Molecular Formula ]:
C₁₄H₁₄D₃NO₈

[ Molecular Weight ]:
330.30500

[ Flash Point ]:
375.6ºC

[ Exact Mass ]:
330.11400

[ PSA ]:
145.55000

[ Vapour Pressure ]:
2.03E-20mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
29389090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation.

Clin. Exp. Pharmacol. Physiol. 36(1) , 35-42, (2009)

1. The aim of the present study was to perform an in vivo estimation of the Michaelis-Menten constants of the major metabolic pathways of paracetamol (APAP). 2. A two-occasion, single-dose cross-over ...

Simultaneous LC-MS/MS quantitation of acetaminophen and its glucuronide and sulfate metabolites in human dried blood spot samples collected by subjects in a pilot clinical study.

Bioanalysis 4(12) , 1429-43, (2012)

In support of a pilot clinical trial using acetaminophen as the model compound to assess dried blood spot (DBS) sampling as the method for clinical pharmacokinetic sample collection, a novel sensitive...

Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.

Int. J. Clin. Pharmacol. Ther. 45(9) , 496-503, (2007)

Paracetamol (PCM) is frequently used in pediatric patients with neoplastic disease. It is metabolized mainly by conjugation, but at therapeutic concentrations, a small fraction of the drug undergoes o...