acetaminophen glucuronide

Modify Date: 2024-01-02 16:18:06

acetaminophen glucuronide Structure
acetaminophen glucuronide structure
Common Name acetaminophen glucuronide
CAS Number 16110-10-4 Molecular Weight 330.30500
Density 1.61g/cm3 Boiling Point 697.4ºC at 760mmHg
Molecular Formula C14H14D3NO8 Melting Point N/A
MSDS USA Flash Point 375.6ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of acetaminophen glucuronide


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].

 Names

Name acetaminophen O-β-D-glucosiduronic acid
Synonym More Synonyms

 acetaminophen glucuronide 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
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

 Safety Information

Symbol GHS07
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

~47%

acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Hayes, John A.; Eccles, Kevin S.; Lawrence, Simon E.; Moynihan, Humphrey A. Carbohydrate Research, 2012 , vol. 349, p. 108 - 112

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acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Hayes, John A.; Eccles, Kevin S.; Lawrence, Simon E.; Moynihan, Humphrey A. Carbohydrate Research, 2012 , vol. 349, p. 108 - 112

~%

acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Hayes, John A.; Eccles, Kevin S.; Lawrence, Simon E.; Moynihan, Humphrey A. Carbohydrate Research, 2012 , vol. 349, p. 108 - 112

~%

acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Smith; Williams Biochemical Journal, 1948 , vol. 42, p. 538,541 Biochemical Journal, 1949 , vol. 44, p. 242,245, 250, 251

~%

acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Boldt, Petra; Rothschild, Markus A.; Kaeferstein, Herbert Arzneimittel-Forschung/Drug Research, 2007 , vol. 57, # 12 p. 787 - 794

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acetaminophen glucuronide Structure

acetaminophen g...

CAS#:16110-10-4

Literature: Wong; Grace Jr.; Wright; Browning; Grossman; Bai; Christ Xenobiotica, 2006 , vol. 36, # 12 p. 1178 - 1190

 Articles25

More 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...

 Synonyms

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