Nabumetone

Base Information

• Chemical Name: Nabumetone
• CAS No.: 42924-53-8
• Molecular Formula: C15H16O2
• Molecular Weight: 228.291
• Hs Code.: 2914500000
• European Community (EC) Number: 641-917-1
• NSC Number: 758623
• UNII: LW0TIW155Z
• DSSTox Substance ID: DTXSID4045472
• Nikkaji Number: J16.442I
• Wikipedia: Nabumetone
• Wikidata: Q425207
• NCI Thesaurus Code: C47627
• RXCUI: 31448
• Pharos Ligand ID: YYRU7YGFQAHC
• Metabolomics Workbench ID: 42809
• ChEMBL ID: CHEMBL1070
• Mol file: 42924-53-8.mol

Synonyms:4-(6-methoxy-2-naphthyl)-2-butanone;Apo-Nabumetone;ApoNabumetone;Arthraxan;BRL 14777;Gen-Nabumetone;Listran;Mebutan;Nabucox;nabumeton;nabumetone;Relafen;Relif;Relifex;Rhoxal nabumetone;Rhoxal-nabumetone

Chemical Property of Nabumetone

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 9.69E-06mmHg at 25°C
• Melting Point: 80-81 °C
• Refractive Index: 1.572
• Boiling Point: 371.1 °C at 760 mmHg
• Flash Point: 165.4 °C
• PSA: 26.30000
• Density: 1.084 g/cm³
• LogP: 3.37000
• Storage Temp.: Refrigerator
• Solubility.: Soluble in alcohol or chloroform
• Water Solubility.: 6mg/L(22.5 oC)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 228.115029749
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

Nabumetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC(=O)CCC1=CC2=C(C=C1)C=C(C=C2)OC
• Recent ClinicalTrials: Single Dose Two-Way Crossover Fed Bioequivalence Study of Nabumetone 750 mg Tablets in Healthy Volunteers
• Recent EU Clinical Trials: The effect of fluvoxamine and ciprofloxacin on the pharmacokinetics and pharmacodynamics of nabumetone: A three-phase double-blind placebo-controlled cross-over study.
• Description: Nabumetone is a non-acidic, nonsteroidal antiinflammatory agent formally related to naproxen. Its main circulating metabolite is 6-methoxy-2-naphthylacetic acid (α-nornaproxen). Administered once daily (Tsub>1/2 * 30 hrs), nabumetone is reported to be effective in the treatment of rheumatoid and osteoarthritis.
• Uses: Anti-inflammatory. Antibacterial. anesthetic (local) Nabumetone is an anti-inflammatory and antibacterial agent (1). A non-steroidal anti-inflammatory prodrug used for treatment of inflammatory and degenerative rheumatic diseases.
• Indications: Nabumetone (Relafen) is approved for rheumatoid arthritis, osteoarthritis, and pain management. Its long half-life allows for once-daily dosing. Although this drug is a weak inhibitor of COX, it is metabolized in the liver to 6-methoxy-2-naphthylacetic acid (6-MNA), a strong COX inhibitor that is chemically similar to naproxen. As with most NSAIDs, GI side effects are most commonly reported. The incidence of gastric ulceration is lower with nabumetone than with many other NSAIDs.This is due to its nature as a prodrug, not to COX-2 selectivity. Lower-bowel complaints, rashes, and CNS disturbances are common adverse effects.
• Therapeutic Function: Antiinflammatory
• Clinical Use: Nabumetone is indicated for the acute and chronic treatment of the signs and symptoms of osteoarthritis and rheumatoid arthritis. The recommended starting dosage is 1,000 mg as a single dose with or without food. More symptomatic relief of severe or persistent symp-toms may be obtained at doses of 1,500 or 2,000 mg/day
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparin, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Nabumetone

There total 34 articles about Nabumetone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-(2-methoxynaphthalene-6-yl)but-3-en-2-one (127053-22-9,56600-90-9) → nabumetone (42924-53-8)

Guidance literature:

With hydrogen; In toluene; at 50 ℃; for 1h; under 3750.38 Torr; Temperature; Pressure; Catalytic behavior; Inert atmosphere; Schlenk technique; Autoclave;

DOI:10.1007/s10562-020-03407-5

Reference yield: 99.0%

methyl vinyl ketone (78-94-4,25038-87-3) + tris(6-methoxy-2-naphthyl)stibine → nabumetone (42924-53-8)

Guidance literature:

With palladium diacetate; silver(I) acetate; acetic acid; at 25 ℃; for 24h;

DOI:10.1246/bcsj.69.2341

Reference yield: 93.0%

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one (73356-31-7,218768-11-7) → nabumetone (42924-53-8)

Guidance literature:

palladium on charcoal catalyst; In acetic acid;

upstream raw materials:

2-hydroxy-3-butene

2-Bromo-6-methoxynaphthalene

methyl magnesium iodide

2-Methoxynaphthalen-6-propionitril

Downstream raw materials:

3,4,5-Trimethoxy-benzoic acid 3-(6-methoxy-naphthalen-2-yl)-1-methyl-propyl ester

(benzo[d][1,3]dioxol-5-yl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

5-(6-methoxynaphthalen-2-yl)-1-p-tolyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

1-(4-chlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Refernces

• 1、 Climent, Maria Jose,Corma, Avelino,Iborra, Sara,Mifsud, Maria. "MgO nanoparticle-based multifunctional catalysts in the cascade reaction allows the green synthesis of anti-inflammatory agents". . p. 223 - 230. Retrieved 2007.
• 2、 Gallou, Fabrice,Gao, Eugene S.,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.. "Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature". supporting information. p. 6055 - 6061. Retrieved 2020/10/14.
• 3、 Donslund, Aske S.,Pedersen, Simon S.,Gaardbo, Cecilie,Neumann, Karoline T.,Kingston, Lee,Elmore, Charles S.,Skrydstrup, Troels. "Direct Access to Isotopically Labeled Aliphatic Ketones Mediated by Nickel(I) Activation". . p. 8099 - 8103. Retrieved 2020/03/16.