MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 527013 | Name: Diclofenac Acyl Glucuronide

Description:

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

Diclofenac Acyl Glucuronide is a major biliary metabolite of Diclofenac (GLXC-07892), a nonsteroidal antiinflammatory drug and COX inhibitor.

Chemical Structure

Diclofenac Acyl Glucuronide
Diclofenac Acyl Glucuronide
CAS#64118-81-6 (Acyl Glucuronide)

Theoretical Analysis

MedKoo Cat#: 527013

Name: Diclofenac Acyl Glucuronide

CAS#: 64118-81-6 (Acyl Glucuronide)

Chemical Formula: C20H19Cl2NO8

Exact Mass: 471.0488

Molecular Weight: 472.27

Elemental Analysis: C, 50.86; H, 4.06; Cl, 15.01; N, 2.97; O, 27.10

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
81811-14-5 (deanol) 119623-66-4 (epolamine) 15307-86-5 (free acid) 15307-79-6 (sodium) 15307-81-0 (Potassium) 78213-16-8 (diethylamine) 64118-81-6 (Acyl Glucuronide)
Synonym
Diclofenac Acyl Glucuronide
IUPAC/Chemical Name
(2S,3S,4S,5R,6S)-6-[2-[2-(2,6-Dichloroanilino)phenyl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChi Key
JXIKYYSIYCILNG-HBWRTXEVSA-N
InChi Code
InChI=1S/C20H19Cl2NO8/c21-10-5-3-6-11(22)14(10)23-12-7-2-1-4-9(12)8-13(24)30-20-17(27)15(25)16(26)18(31-20)19(28)29/h1-7,15-18,20,23,25-27H,8H2,(H,28,29)/t15-,16-,17+,18-,20+/m0/s1
SMILES Code
O=C([C@H]1O[C@@H](OC(CC2=CC=CC=C2NC3=C(Cl)C=CC=C3Cl)=O)[C@H](O)[C@@H](O)[C@@H]1O)O
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
>2 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 472.27 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: Lazarska KE, Dekker SJ, Vermeulen NPE, Commandeur JNM. Effect of UGT2B7*2 and CYP2C8*4 polymorphisms on diclofenac metabolism. Toxicol Lett. 2017 Dec 2;284:70-78. doi: 10.1016/j.toxlet.2017.11.038. [Epub ahead of print] PubMed PMID: 29203276. 2: Scialis RJ, Manautou JE. Elucidation of the Mechanisms through Which the Reactive Metabolite Diclofenac Acyl Glucuronide Can Mediate Toxicity. J Pharmacol Exp Ther. 2016 Apr;357(1):167-76. doi: 10.1124/jpet.115.230755. Epub 2016 Feb 11. PubMed PMID: 26869668; PubMed Central PMCID: PMC4809317. 3: Syed M, Skonberg C, Hansen SH. Mitochondrial toxicity of diclofenac and its metabolites via inhibition of oxidative phosphorylation (ATP synthesis) in rat liver mitochondria: Possible role in drug induced liver injury (DILI). Toxicol In Vitro. 2016 Mar;31:93-102. doi: 10.1016/j.tiv.2015.11.020. Epub 2015 Nov 25. PubMed PMID: 26627130. 4: Scialis RJ, Csanaky IL, Goedken MJ, Manautou JE. Multidrug Resistance-Associated Protein 3 Plays an Important Role in Protection against Acute Toxicity of Diclofenac. Drug Metab Dispos. 2015 Jul;43(7):944-50. doi: 10.1124/dmd.114.061705. Epub 2015 Apr 20. PubMed PMID: 25897176; PubMed Central PMCID: PMC4468432. 5: Niu X, de Graaf IA, Langelaar-Makkinje M, Horvatovich P, Groothuis GM. Diclofenac toxicity in human intestine ex vivo is not related to the formation of intestinal metabolites. Arch Toxicol. 2015 Jan;89(1):107-19. doi: 10.1007/s00204-014-1242-6. Epub 2014 Apr 26. PubMed PMID: 24770551. 6: Lee HJ, Lee E, Yoon SH, Chang HR, Kim K, Kwon JH. Enzymatic and microbial transformation assays for the evaluation of the environmental fate of diclofenac and its metabolites. Chemosphere. 2012 May;87(8):969-74. doi: 10.1016/j.chemosphere.2012.02.018. Epub 2012 Mar 7. PubMed PMID: 22401746. 7: van Midwoud PM, Janssen J, Merema MT, de Graaf IA, Groothuis GM, Verpoorte E. On-line HPLC analysis system for metabolism and inhibition studies in precision-cut liver slices. Anal Chem. 2011 Jan 1;83(1):84-91. doi: 10.1021/ac1018638. Epub 2010 Dec 3. PubMed PMID: 21128611. 8: Lagas JS, Sparidans RW, Wagenaar E, Beijnen JH, Schinkel AH. Hepatic clearance of reactive glucuronide metabolites of diclofenac in the mouse is dependent on multiple ATP-binding cassette efflux transporters. Mol Pharmacol. 2010 Apr;77(4):687-94. doi: 10.1124/mol.109.062364. Epub 2010 Jan 19. PubMed PMID: 20086033. 9: Obach RS. Glycerolysis of acyl glucuronides as an artifact of in vitro drug metabolism incubations. Drug Metab Dispos. 2009 Aug;37(8):1581-6. doi: 10.1124/dmd.109.027953. Epub 2009 May 13. PubMed PMID: 19439485. 10: Sparidans RW, Lagas JS, Schinkel AH, Schellens JH, Beijnen JH. Liquid chromatography-tandem mass spectrometric assay for diclofenac and three primary metabolites in mouse plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Sep 1;872(1-2):77-82. doi: 10.1016/j.jchromb.2008.07.012. Epub 2008 Jul 18. PubMed PMID: 18674973. 11: Naisbitt DJ, Sanderson LS, Meng X, Stachulski AV, Clarke SE, Park BK. Investigation of the immunogenicity of diclofenac and diclofenac metabolites. Toxicol Lett. 2007 Jan 10;168(1):45-50. Epub 2006 Nov 10. PubMed PMID: 17123753. 12: Wang J, Davis M, Li F, Azam F, Scatina J, Talaat R. A novel approach for predicting acyl glucuronide reactivity via Schiff base formation: development of rapidly formed peptide adducts for LC/MS/MS measurements. Chem Res Toxicol. 2004 Sep;17(9):1206-16. PubMed PMID: 15377154. 13: Kenny JR, Maggs JL, Meng X, Sinnott D, Clarke SE, Park BK, Stachulski AV. Syntheses and characterization of the acyl glucuronide and hydroxy metabolites of diclofenac. J Med Chem. 2004 May 20;47(11):2816-25. PubMed PMID: 15139759. 14: Grillo MP, Hua F, Knutson CG, Ware JA, Li C. Mechanistic studies on the bioactivation of diclofenac: identification of diclofenac-S-acyl-glutathione in vitro in incubations with rat and human hepatocytes. Chem Res Toxicol. 2003 Nov;16(11):1410-7. PubMed PMID: 14615966. 15: Grillo MP, Knutson CG, Sanders PE, Waldon DJ, Hua F, Ware JA. Studies on the chemical reactivity of diclofenac acyl glucuronide with glutathione: identification of diclofenac-S-acyl-glutathione in rat bile. Drug Metab Dispos. 2003 Nov;31(11):1327-36. PubMed PMID: 14570764. 16: Sallustio BC, Holbrook FL. In vivo perturbation of rat hepatocyte canalicular membrane function by diclofenac. Drug Metab Dispos. 2001 Dec;29(12):1535-8. PubMed PMID: 11717171. 17: Seitz S, Boelsterli UA. Diclofenac acyl glucuronide, a major biliary metabolite, is directly involved in small intestinal injury in rats. Gastroenterology. 1998 Dec;115(6):1476-82. PubMed PMID: 9834275. 18: Kretz-Rommel A, Boelsterli UA. Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos. 1994 Nov-Dec;22(6):956-61. PubMed PMID: 7895615. 19: Kretz-Rommel A, Boelsterli UA. Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol Appl Pharmacol. 1993 May;120(1):155-61. PubMed PMID: 8511777. 20: Tsuchiya T, Terakawa M, Ishibashi K, Noguchi H, Kato R. Disposition and enterohepatic circulation of diclofenac in dogs. Arzneimittelforschung. 1980;30(10):1650-3. PubMed PMID: 7192104.