Nabumetone

  • CAT Number: A000640
  • CAS Number: 42924-53-8
  • Molecular Formula: C15H16O2
  • Molecular Weight: 228.3
  • Purity: ≥95%
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Nabumetone is a non-steroidal anti-inflammatory drug (NSAID), the only 1-naphthaleneacetic acid derivative. It is a nonacidic NSAID that is rapidly metabolized in the liver to a major active metabolite, 6-methoxy-2-naphthyl acetic acid. As found with previous NSAIDs, nabumetone/’s active metabolite inhibits the cyclooxygenase enzyme and preferentially blocks COX-2 activity (which is indirectly responsible for the production of inflammation and pain during arthritis). The active metabolite of nabumetone is felt to be the compound primarily responsible for therapeutic effect. Comparatively, the parent drug is a poor inhibitor of COX-2 byproducts, particularly prostaglandins. It may be less nephrotoxic than indomethacin.

Catalog Number A000640
CAS Number 42924-53-8
Molecular Formula

C15H16O2

Purity 95%
Target COX
Solubility Soluble in DMSO > 10 mM
Storage -20°C
InChI 1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
InChIKey BLXXJMDCKKHMKV-UHFFFAOYSA-N
SMILES CC(=O)CCC1=CC2=C(C=C1)C=C(C=C2)OC
Reference

1: Suárez D, Díaz N. Conformational and entropy analyses of extended molecular
dynamics simulations of α-, β- and γ-cyclodextrins and of the
β-cyclodextrin/nabumetone complex. Phys Chem Chem Phys. 2017 Jan
4;19(2):1431-1440. doi: 10.1039/c6cp06107a. PubMed PMID: 27982145.
<br>

2: Goodwin DJ, Martini LG, Lawrence MJ. Production of nabumetone nanoparticles:
Effect of molecular weight, concentration and nature of cellulose ether
stabiliser. Int J Pharm. 2016 Dec 5;514(2):428-444. doi:
10.1016/j.ijpharm.2016.09.079. Epub 2016 Sep 29. PubMed PMID: 27693736.

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3: Balap A, Lohidasan S, Sinnathambi A, Mahadik K. Pharmacokinetic and
Pharmacodynamic Interaction of Andrographolide and Standardized Extract of
Andrographis paniculata (Nees) with Nabumetone in Wistar Rats. Phytother Res.
2017 Jan;31(1):75-80. doi: 10.1002/ptr.5731. Epub 2016 Oct 7. PubMed PMID:
27714886.

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4: Hung SC, Liao KF, Hung HC, Lin CL, Lai SW, Lin CH. Nabumetone use and risk of
acute pancreatitis in a case-control study. Pancreatology. 2016
May-Jun;16(3):353-7. doi: 10.1016/j.pan.2016.03.003. Epub 2016 Mar 11. PubMed
PMID: 27029853.
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5: Asadi M, Haji Shabani AM, Dadfarnia S, Abbasi B. Vortex-assisted
surfactant-enhanced emulsification microextraction based on solidification of
floating organic drop combined with high performance liquid chromatography for
determination of naproxen and nabumetone. J Chromatogr A. 2015 Dec 18;1425:17-24.
doi: 10.1016/j.chroma.2015.11.005. Epub 2015 Nov 19. PubMed PMID: 26627589.
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6: Světlík S, &#352;tícha M, Matou&#353;ková O, Nespě&#353;ná L, Sklená&#345; Z, Bart&#367;něk A, Perlík
F, Slana&#345; O. Nabumetone and 6-MNA Pharmacokinetics, Assessment of Intrasubject
Variability and Gender Effect. Am J Ther. 2016 Nov/Dec;23(6):e1498-e1503. PubMed
PMID: 25393072.

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7: Matsumoto K, Hasegawa T, Koyanagi J, Takahashi T, Akimoto M, Sugibayashi K.
Reductive metabolism of nabumetone by human liver microsomal and cytosolic
fractions: exploratory prediction using inhibitors and substrates as marker
probes. Eur J Drug Metab Pharmacokinet. 2015 Jun;40(2):127-35. PubMed PMID:
24659525.
<br>

8: Varfaj F, Zulkifli SN, Park HG, Challinor VL, De Voss JJ, Ortiz de Montellano
PR. Carbon-carbon bond cleavage in activation of the prodrug nabumetone. Drug
Metab Dispos. 2014 May;42(5):828-38. doi: 10.1124/dmd.114.056903. Epub 2014 Feb
28. PubMed PMID: 24584631; PubMed Central PMCID: PMC3989788.
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9: &#268;eslová L, Hol&#269;apek M, Nobilis M. Identification of combined conjugation of
nabumetone phase I metabolites with glucuronic acid and glycine in minipig
biotransformation using coupling high-performance liquid chromatography with
electrospray ionization mass spectrometry. J Pharm Biomed Anal. 2014
Jan;88:221-4. doi: 10.1016/j.jpba.2013.08.053. Epub 2013 Sep 12. PubMed PMID:
24083957.
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10: Perez-Ezquerra PR, Sanchez-Morillas L, Laguna Martinez JJ, Gonzalez Mendiola
R, Gomez-Traseira C, Carrasco Garcia I, Herranz Ma&#241;as M, Rubio Matos A.
Hypersensitivity to nabumetone: cross reactivity with naproxen. Ann Allergy
Asthma Immunol. 2013 Jul;111(1):74-5. doi: 10.1016/j.anai.2013.05.006. PubMed
PMID: 23806470.

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