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Nabumetone

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Nabumetone
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa692022
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding> 99% (active metabolite)
MetabolismHepatic, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA
Elimination half-life23 hours (active metabolite)
ExcretionRenal
Identifiers
  • 4-(6-methoxy-2-naphthyl)-2-butanone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.169.752 Edit this at Wikidata
Chemical and physical data
FormulaC15H16O2
Molar mass228.29 g/mol g·mol−1
3D model (JSmol)
  • O=C(C)CCc1ccc2c(c1)ccc(OC)c2
  • 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 checkY
  • Key:BLXXJMDCKKHMKV-UHFFFAOYSA-N checkY
  (verify)

Nabumetone is a non-steroidal anti-inflammatory drug[2] (NSAID), the only 1-naphthaleneacetic acid derivative. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex and Gambaran.

Introduction

Nabumetone is a non acidic NSAID (Non-steroidal anti-inflammatory drug) 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 preferentially blocks cyclo-oxygenase-2 activity which is indirectly responsible for the production of inflammation and pain during arthritis by way of enhancing the production of endoperoxides and prostaglandins E2 and I2 (prostacyclin). 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 prostaglandin synthesis. It may be less nephrotoxic than indomethacin which decreases the excretion of 6-oxo-PGF1a by inhibition of cyclooxygenase- 1 or by inhibition of specific exercise-induced activation of cyclo-oxygenase-2, or both [3]. Nabumetone belongs to a new class of NSAID with a low potential for causing gastrointestinal mucosal irritancy and inhibition of platelet function [4] and has little effect on renal prostaglandin secretion and had less of an association with CHF (congestive heart failure) than other traditional drugs of the class [5]. Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors is also good i.e. equivalent to paracetamol [6].

Uses

It is used to treat pain or inflammation caused by arthritis. Nabumetone works by reducing the effects of hormones that cause pain and inflammation.

Side effects

It has been shown to have a slightly lower risk of gastrointestinal side effects than most other non-selective NSAIDs since it is a non-acidic prodrug which is then metabolized to its active 6MNA (6-methoxy-2-naphthylacetic acid) form.

Assay of Nabumetone[7]

There are few papers published reporting analytical methods [8] for nabumetone. Two of them employed HPLC with UV-detection [9] [10]. One HPLC method using direct injection on restricted access media columns [11]. Flow injection analysis (FIA) with UV-detection was also reported for the determination of nabumetone in pharmaceutical preparations [12]. Methods using HPLC with fluorescence detection [13] [14] [15] [16] were reported. M. Nobilis et al. carried out biotransformation and disposition studies in humans and minipigs using HPLC with UV, fluorescence and mass spectrometric detection. The interactions with gamma-cyclodextrin were also studied by fluorescence measurements13. Assay methods employed HPLC using UV detection[17], photodiode array (PDA) detector[18] [19] and mass spectrometric detection for the determination of nabumetone and its metabolites. Murillo Pulgarín et al. [20] [21] [22] reported three analytical methods using different techniques along with phosphorescence. Liquid chromatography methods using different techniques of mass spectrometry were also reported [23] [24] [25]. The electrochemical behavior of nabumetone by a voltammetric technique [26] and a novel colorimetric method based on chemical derivatization [27] were also published.

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Gonzalo-Garijo MA, Cordobés-Duran C, Lamilla-Yerga AM, Moreno-Gastón I (2007). "Severe immediate reaction to nabumetone". Journal of Investigational Allergology and Clinical Immunology : official organ of the International Association of Asthmology (INTERASMA) and Sociedad Latinoamericana de Alergia e Inmunología. 17 (4): 274–6. PMID 17694703.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Olsen N V, Jensen N G, Hansen J M, Christensen N J, Fogh-Andersen N and Kanstrup I L, Clin Sci.,1999, 97, 457- 465.
  4. ^ Kristensen Jrgen, Viklund Andreas, Feltelius Nils and Larsson Anders, Platelets. 1996, 7, 149 - 152.
  5. ^ Donnan P T, Pharmacoepidemiol Drug Safety, 2000, 8, 115.
  6. ^ Palmer Robert H, Haig Ann E, Flavin Susan K and Iyengar Malini K, Am J Hypertens. 2001, 14, 85A.
  7. ^ Prafulla Kumar Sahu and M. Mathrusri Annapurna, Analytical method development by liquid chromatography, LAP Lambert Academic Publisher, Germany, 2011
  8. ^ Starek Małgorzata and Krzek Jan, Talanta, 2009, 77, 925-942.
  9. ^ Al-Momani Idrees F, Anal Lett., 1997, 30, 2485-2492.
  10. ^ Jang E J, Lee Y J, Park M G and Shim C K, Anal Lett., 1995, 28, 2379-2389.
  11. ^ Haque Ahsanul and Stewart James T, Biomed Chromatogr., 1999, 13, 51-56.
  12. ^ Can N O, Tuncel M and Aboul-Enein H Y, Pharmazie., 2003, 58, 22-24.
  13. ^ Mikami E, Goto T, Ohno T, Matsumoto H and Nishida M, J Pharm Biomed Anal., 2000, 23, 917-925.
  14. ^ ska Kamila Kobyli, Ska Ma gorzata Barli and Ska Maria Kobyli, J Pharm Biomed Anal., 2003, 32, 323-328.
  15. ^ Nobilis M, Kopecký J, Tina J Kv, Svoboda Z, Pour M, Kune J, Apek M Hol and Ová L Kolá, J Pharm Biomed Anal., 2003, 32, 641-656.
  16. ^ Al-Rawashdeh A F Nathir, J Inclusion Phenomena and Macrocyclic Chem. 2005, 51(1-2), 27-32.
  17. ^ Prafulla Kumar Sahu and M. Mathrusri Annapurna, Analysis of Nabumetone in Bulk and Tablet Formulation by a New and Validated Reverse Phase High Performance Liquid Chromatography.E-Journal of Chemistry, 2009, 6(S1), S59- S64.
  18. ^ Rao R Nageswara, Meena S, Nagaraju D and Rao A Raghu Ram, Biomed Chromatogr., 2004, 19, 362-368.
  19. ^ Nobilis M, Holcapek M, Kolárová L, Kopecký J, Kunes M, Svoboda Z and Kvetina J, J Chromatogr. A, 2004, 1031, 229-236.
  20. ^ Pulgarín J A Murillo, Molina A Alañón and Pardo M T Alañón, Analytica Chimica Acta, 2005, 528, 77-82.
  21. ^ Pulgarín J A Murillo, Molina A Alañón and Pardo M T Alañón, Anal Biochem., 2005, 339, 157-164.
  22. ^ Pulgarín Jose A Murillo, Molina Aurelia Alañón and Robles Ignacio Sánchez-Ferrer, Analytica Chimica Acta. 2005, 554, 37-42.
  23. ^ Patel Bhavin N, Sharma Naveen, Sanyal Mallika, Prasad Arpana and Shrivastav Pranav S, Biomed Chromatogr., 2008, 22, 1213-1224.
  24. ^ Wolff J C, Hawtin P N, Monté S, Balogh M and Jones T, Rapid Commun Mass Spectrom., 2001, 15, 265-272.
  25. ^ Sheen J F and Her G R, Anal Bioanal Chem. 2004, 380, 7-8.
  26. ^ Altun Yuksel, Dogan Burcu, Ozkan Sibel A and Uslu Bengi, Acta Chim Slov., 2007, 54, 287-294.
  27. ^ Adegoke A O, Idowu S O and Olaniyi A A, Afr J Med Med Sci., 2007, 36, 249-257.


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