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MedKoo Cat#: 574201 | Name: Acetaminophen glucuronide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acetaminophen glucuronide is an inactive metabolite of the analgesic and antipyretic agent acetaminophen. It is formed via glucuronidation of acetaminophen by the UDP-glucuronosyltransferase (UGT) isoforms UGT1A6, UGT1A9, UGT1A1, and UGT2B15.

Chemical Structure

Acetaminophen glucuronide
Acetaminophen glucuronide
CAS#120595-80-4 (sodium)

Theoretical Analysis

MedKoo Cat#: 574201

Name: Acetaminophen glucuronide

CAS#: 120595-80-4 (sodium)

Chemical Formula: C14H16NNaO8

Exact Mass: 349.0774

Molecular Weight: 349.27

Elemental Analysis: C, 48.14; H, 4.62; N, 4.01; Na, 6.58; O, 36.65

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
16110-10-4 (free acid) 120595-80-4 (sodium)
Synonym
Acetaminophen glucuronide, 4-Acetamidophenol Glucuronide, APAP Glucuronide, 4'-Hydroxyacetanilide Glucuronide, Paracetamol Glucuronide
IUPAC/Chemical Name
sodium (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate
InChi Key
OINXIJJEOMGKPB-CYRSAHDMSA-M
InChi Code
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
SMILES Code
CC(NC1=CC=C(O[C@@H]2O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]2O)C=C1)=O.[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 349.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ji Y, Azuine RE, Zhang Y, Hou W, Hong X, Wang G, Riley A, Pearson C, Zuckerman B, Wang X. Association of Cord Plasma Biomarkers of In Utero Acetaminophen Exposure With Risk of Attention-Deficit/Hyperactivity Disorder and Autism Spectrum Disorder in Childhood. JAMA Psychiatry. 2020 Feb 1;77(2):180-189. doi: 10.1001/jamapsychiatry.2019.3259. PMID: 31664451; PMCID: PMC6822099. 2: Noda T, Kato R, Ozato Y, Kawai Y, Yamamoto M, Kagawa Y, Azuma M, Yamamoto K, Kusanagi M, Uryu K, Harada H, Ijiri Y, Hayashi T, Tanaka K. Decreased plasma acetaminophen glucuronide/acetaminophen concentration ratio warns the onset of acetaminophen-induced liver injury. Biopharm Drug Dispos. 2022 Jun;43(3):108-116. doi: 10.1002/bdd.2316. Epub 2022 May 17. PMID: 35508086. 3: Barosa C, Jones JG, Rizza R, Basu A, Basu R. Acetaminophen glucuronide and plasma glucose report identical estimates of gluconeogenesis and glycogenolysis for healthy and prediabetic subjects using the deuterated water method. Magn Reson Med. 2013 Aug;70(2):315-9. doi: 10.1002/mrm.24485. Epub 2012 Sep 28. PMID: 23023691; PMCID: PMC3724365. 4: Jones J, Kahl S, Carvalho F, Barosa C, Roden M. Simplified analysis of acetaminophen glucuronide for quantifying gluconeogenesis and glycogenolysis using deuterated water. Anal Biochem. 2015 Jun 15;479:37-9. doi: 10.1016/j.ab.2015.03.018. Epub 2015 Mar 20. PMID: 25800563. 5: Sabordo L, Sallustio BC, Evans AM, Nation RL. Hepatic disposition of the acyl glucuronide 1-O-gemfibrozil-beta-D-glucuronide: effects of clofibric acid, acetaminophen, and acetaminophen glucuronide. J Pharmacol Exp Ther. 2000 Oct;295(1):44-50. PMID: 10991959. 6: Zhang X, Li R, Hu W, Zeng J, Jiang X, Wang L. A reliable LC-MS/MS method for the quantification of N-acetyl-p-benzoquinoneimine, acetaminophen glutathione and acetaminophen glucuronide in mouse plasma, liver and kidney: Method validation and application to a pharmacokinetic study. Biomed Chromatogr. 2018 Nov;32(11):e4331. doi: 10.1002/bmc.4331. Epub 2018 Sep 6. PMID: 29978489. 7: Achterbergh R, Lammers LA, Klümpen HJ, Mathôt RAA, Romijn JA. Short-Term High-Fat Diet Alters Acetaminophen Metabolism in Healthy Individuals. Ther Drug Monit. 2022 Dec 1;44(6):797-804. doi: 10.1097/FTD.0000000000000993. PMID: 35500453. 8: Tzoulaki I, Castagné R, Boulangé CL, Karaman I, Chekmeneva E, Evangelou E, Ebbels TMD, Kaluarachchi MR, Chadeau-Hyam M, Mosen D, Dehghan A, Moayyeri A, Ferreira DLS, Guo X, Rotter JI, Taylor KD, Kavousi M, de Vries PS, Lehne B, Loh M, Hofman A, Nicholson JK, Chambers J, Gieger C, Holmes E, Tracy R, Kooner J, Greenland P, Franco OH, Herrington D, Lindon JC, Elliott P. Serum metabolic signatures of coronary and carotid atherosclerosis and subsequent cardiovascular disease. Eur Heart J. 2019 Sep 7;40(34):2883-2896. doi: 10.1093/eurheartj/ehz235. PMID: 31102408; PMCID: PMC7963131. 9: Abernethy DR, Greenblatt DJ, Ameer B, Shader RI. Probenecid impairment of acetaminophen and lorazepam clearance: direct inhibition of ether glucuronide formation. J Pharmacol Exp Ther. 1985 Aug;234(2):345-9. PMID: 4020675. 10: Zhao Y, Harmatz JS, Epstein CR, Nakagawa Y, Kurosaki C, Nakamura T, Kadota T, Giesing D, Court MH, Greenblatt DJ. Favipiravir inhibits acetaminophen sulfate formation but minimally affects systemic pharmacokinetics of acetaminophen. Br J Clin Pharmacol. 2015 Nov;80(5):1076-85. doi: 10.1111/bcp.12644. Epub 2015 Jun 8. PMID: 25808818; PMCID: PMC4631180. 11: Lecoeur M, Rabenirina G, Schifano N, Odou P, Ethgen S, Lebuffe G, Foulon C. Determination of acetaminophen and its main metabolites in urine by capillary electrophoresis hyphenated to mass spectrometry. Talanta. 2019 Dec 1;205:120108. doi: 10.1016/j.talanta.2019.07.003. Epub 2019 Jul 2. PMID: 31450387. 12: Levy G, Khanna NN, Soda DM, Tsuzuki O, Stern L. Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion. Pediatrics. 1975 Jun;55(6):818-25. PMID: 1134883. 13: Xu R, Wang Q, Zhang J, Zang M, Liu X, Yang J. Changes in pharmacokinetic profiles of acetaminophen and its glucuronide after pretreatment with combinations of N-acetylcysteine and either glycyrrhizin, silibinin or spironolactone in rat. Xenobiotica. 2014 Jun;44(6):541-6. doi: 10.3109/00498254.2013.858849. Epub 2013 Nov 19. PMID: 24251357. 14: Owens KH, Murphy PG, Medlicott NJ, Kennedy J, Zacharias M, Curran N, Sreebhavan S, Thompson-Fawcett M, Reith DM. Population pharmacokinetics of intravenous acetaminophen and its metabolites in major surgical patients. J Pharmacokinet Pharmacodyn. 2014 Jun;41(3):211-21. doi: 10.1007/s10928-014-9358-0. Epub 2014 May 21. PMID: 24846170. 15: Rother KI, Schwenk WF. Hepatic glycogen accurately reflected by acetaminophen glucuronide in dogs refed after fasting. Am J Physiol. 1995 Oct;269(4 Pt 1):E766-73. doi: 10.1152/ajpendo.1995.269.4.E766. PMID: 7485493. 16: Alkharfy KM, Frye RF. High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. J Chromatogr B Biomed Sci Appl. 2001 Apr 5;753(2):303-8. doi: 10.1016/s0378-4347(00)00566-1. PMID: 11334344. 17: Slattery JT, Koup JR, Levy G. Acetaminophen pharmacokinetics after overdose. Clin Toxicol. 1981 Jan;18(1):111-7. doi: 10.3109/15563658108990016. PMID: 7471662. 18: Villanueva SS, Ruiz ML, Ghanem CI, Luquita MG, Catania VA, Mottino AD. Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats. Drug Metab Dispos. 2008 Mar;36(3):475-80. doi: 10.1124/dmd.107.018127. Epub 2007 Dec 20. PMID: 18096675. 19: Zamek-Gliszczynski MJ, Nezasa K, Tian X, Bridges AS, Lee K, Belinsky MG, Kruh GD, Brouwer KL. Evaluation of the role of multidrug resistance-associated protein (Mrp) 3 and Mrp4 in hepatic basolateral excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in Abcc3-/- and Abcc4-/- mice. J Pharmacol Exp Ther. 2006 Dec;319(3):1485-91. doi: 10.1124/jpet.106.110106. Epub 2006 Sep 20. PMID: 16988054. 20: Ghanem CI, Ruiz ML, Villanueva SS, Luquita MG, Catania VA, Jones B, Bengochea LA, Vore M, Mottino AD. Shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats. J Pharmacol Exp Ther. 2005 Dec;315(3):987-95. doi: 10.1124/jpet.105.090613. Epub 2005 Aug 18. PMID: 16109740.