Delving into the Latest Updates on Nabumetone with Synapse

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

4-(6-Methoxy-2-naphthalenyl)-2-butanone, 4-(6-Methoxy-2-naphthyl)-2-butanone, Nabumetone (JP17/USP/INN)

+ [10]

Target

COX

Mechanism

COX inhibitors(Cyclooxygenases inhibitors)

Therapeutic Areas

Immune System DiseasesNervous System DiseasesSkin and Musculoskeletal Diseases+ [1]

Active Indication

OsteoarthritisLow Back PainRheumatoid Arthritis+ [4]

Inactive Indication-

Originator Organization

GSK Plc

Active Organization

Sanwa Kagaku Kenkyusho Co., Ltd.

GSK Plc

Inactive Organization

Smithkline Beecham Plc

Drug Highest PhaseApproved

First Approval Date

(01 Jan 1984),

ArthritisPainRheumatic Diseases+ [1]

RegulationOrphan Drug (US)

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Structure

Molecular FormulaC15H16O2

InChIKeyBLXXJMDCKKHMKV-UHFFFAOYSA-N

CAS Registry42924-53-8

The use of small organic molecules, such as chalcones, for efficient applications as organic luminescent materials has attracted increasing attention owing to their interesting optical, photophysical, and biological properties. In this study, a new chalcone, 1-(4-isopropylphenyl)-5-(6-methoxynaphthalen-2-yl)pent-1-en-3-one (INM), was synthesized via base condensation between nabumetone and cuminaldehyde. INM was subsequently identified and characterized by FT-IR, NMR spectroscopy (¹H and ¹³C), mass spectrometry, elemental analysis, X-ray diffraction, thermogravimetric analysis, and FESEM studies. Investigation of the solvent effect revealed that the π → π* transition involved a bathochromic shift from hexane to water and a large Stokes-shifted, twisted intramolecular charge-transfer emission in water. Diffuse reflectance spectral studies confirmed the formation of transparent INM chalcones with excellent crystallinity, and photoluminescence studies substantiated the low recombination rate of electrons and holes. Tauc plot analysis with the Kubelka-Munk algorithm revealed higher direct (3.57 eV) and indirect (3.41 eV) bandgap energies of INM. Density functional theory calculations at B3LYP/6-31G(d,p) revealed that INM had promising nonlinear optical activity (β ≈ 30.504 × 10^-30 compared to a reference material, urea. Cell biocompatibility was evaluated after culturing skin fibroblasts and breast cancer cells with INM using the MTT assay and fluorescence microscopy of the live/dead cell assay. It was observed that INM exhibited good NIH/3T3 cell adhesion and proliferation and the weak inhibiting ability of MDA-MB231.

01 Aug 2024·Journal of Environmental Sciences

Degradation behaviors of Nabumetone and its metabolite during UV/monochloramine process: Experimental and theoretical study

Article

Author: Tu, Xiang ; Bai, Yunsong ; Fu, Qing ; Zhang, Kunfeng ; Fu, Yifu ; Xiao, Ruiyang ; Zhang, Qi ; Chang, Sheng ; Pan, Yang

This study investigated degradation behaviors of a nonsteroidal anti-inflammatory drug Nabumetone (NMT) and its major metabolite 6-methoxy-2-naphthylacetic acid (MNA) in the coupling process of ultraviolet and monochloramine (UV/NH₂Cl). The second-order rate constants of the contaminants reacting with reactive radicals (HO•, Cl•, Cl₂•^⁻, and CO₃•^⁻) were determined by laser flash photolysis experiments. HO• and Cl• contributed predominantly with 52.3% and 21.7% for NMT degradation and 60.8% and 22.3% for MNA degradation. The presence of chlorides retarded the degradation of NMT, while promoted the destruction of MNA, which was ascribed to the photosensitization effects of MNA under UV irradiation. Density functional theory (DFT) calculations revealed that radical adduct formation (RAF) was dominant pathway for both HO• and Cl• reacting with the contaminants, and hydrogen atom transfer (HAT) preferred to occur on side chains of NMT and MNA. NMT reacted with NO₂• through single electron transfer (SET) with the second-order rate constant calculated to be 5.35 × 10⁷ (mol/L)^-1 sec^-1, and the contribution of NO₂• was predicted to be 13.0% of the total rate constant of NMT in pure water, which indicated that NO₂• played a non-negligible role in the degradation of NMT. The acute toxicity and developmental toxicity of NMT were enhanced after UV/NH₂Cl treatment, while those of MNA were alleviated. The transformation products of both NMT and MNA exhibited higher mutagenicity than their parent compounds. This study provides a deep understanding of the mechanism of radical degradation of NMT and MNA in the treatment of UV/NH₂Cl.

01 Feb 2024·Chemosphere

Nabumetone and flufenamic acid pose a serious risk to aquatic plants: A study with Chlamydomonas reinhardtii as a model organism

Article

Author: Kapuścińska, Dominika ; Liakh, Ivan ; Narajczyk, Magdalena ; Wielgomas, Bartosz ; Aksmann, Anna

The aquatic environment is constantly under threat due to the release of numerous pollutants. Among them, pharmaceuticals constitute a huge and diverse group. Non-steroidal anti-inflammatory drugs (NSAIDs) are increasingly found in water bodies, but knowledge about their potential toxicity is still low. In particular, there is a lack of information about their influences on aquatic plants and algae. We estimated the susceptibility of the microalgae Chlamydomonas reinhardtii to nabumetone (NBT) and flufenamic acid (FFA), focusing on photosynthesis. Due to the differences in the structures of these compounds, it was assumed that these drugs would have different toxicities to the tested green algae. The hypothesis was confirmed by determining the effective concentration values, the intensity of photosynthesis, the intensity of dark respiration, the contents of photosynthetic pigments, the fluorescence of chlorophyll a in vivo (OJIP test), and cell ultrastructure analysis. Assessment of the toxicity of the NSAIDs was extended by the calculation of an integrated biomarker response index (IBR), which is a valuable tool in ecotoxicological studies. The obtained results indicate an over six times higher toxicity of NBT compared to FFA. After analysis of the chlorophyll a fluorescence in vivo, it was found that NBT inhibited electron transport beyond the PS II. FFA, unlike NBT, lowered the intensity of photosynthesis, probably transforming some reaction centers into "silent centers", which dissipate energy as heat. The IBR estimated based on photosynthetic parameters suggests that the toxic effect of FFA results mainly from photosynthesis disruption, whereas NBT significantly affects other cellular processes. No significant alteration in the ultrastructure of treated cells could be seen, except for changes in starch grain number and autophagic vacuoles that appeared in FFA-treated cells. To the best of our knowledge, this is the first work reporting the toxic effects of NBT and FFA on unicellular green algae.

100 Deals associated with Nabumetone

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External Link

KEGG	Wiki	ATC	Drug Bank
D00425	Nabumetone	M01AX01	DB00461

R&D Status

10 top approved records.

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Indication	Country/Location	Organization	Date
Osteoarthritis	JP	Sanwa Kagaku Kenkyusho Co., Ltd.	03 Mar 1993
Low Back Pain	JP	Sanwa Kagaku Kenkyusho Co., Ltd.	30 Mar 1990
Rheumatoid Arthritis	JP	Sanwa Kagaku Kenkyusho Co., Ltd.	30 Mar 1990
Arthritis	-	GSK Plc	01 Jan 1984
Pain	-	GSK Plc	01 Jan 1984
Rheumatic Diseases	-	GSK Plc	01 Jan 1984
Soft Tissue Injuries	-	GSK Plc	01 Jan 1984

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Clinical Result

Indication

Phase

Evaluation

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Study	Phase	Population	Analyzed Enrollment	Group	Results	Evaluation	Publication Date


UEGW2020	Not Applicable	-	-	Nabumetone 1000 mg	tkqcwncnnt(nqsieuhyfk) = kcocsclgep fynlobhgfr (fgmqbbaicc, 1.0) View more	-	01 Oct 2020
				Nabumetone 2000 mg	tkqcwncnnt(nqsieuhyfk) = rehdtwfobt fynlobhgfr (fgmqbbaicc, 1.2) View more
EULAR2003	Not Applicable	Osteoarthritis	2,020	Rofecoxib 12.5 mg	(lbbuclpunu) = The incidence of adverse events including hypertension and lower extremity edema was similar among active treatments nepjxdrsks (cqrpakjsea )	Positive	18 Jun 2003
				Nabumetone 1000 mg