ChemicalBook
Chinese Japanese Germany Korea

Nabumetone

Nabumetone
Nabumetone structure
CAS No.
42924-53-8
Chemical Name:
Nabumetone
Synonyms
RELAFEN;relifex;Nabumeton;brl147777;BRL-14777;NABUMETONE;Nabumetone RS;Nabumetone CRS;Nabumetone (DMF);Nabumetone (200 mg)
CBNumber:
CB2386779
Molecular Formula:
C15H16O2
Formula Weight:
228.29
MOL File:
42924-53-8.mol

Nabumetone Properties

Melting point:
80-810C
Boiling point:
330.1°C (rough estimate)
Density 
1.0657 (rough estimate)
refractive index 
1.5542 (estimate)
storage temp. 
Sealed in dry,2-8°C
solubility 
Soluble in alcohol or chloroform
form 
neat
Water Solubility 
6mg/L(22.5 ºC)
CAS DataBase Reference
42924-53-8(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
LW0TIW155Z
ATC code
M01AX01
NIST Chemistry Reference
Nabumetone(42924-53-8)
SAFETY
  • Risk and Safety Statements
Hazard statements  H303
Hazard Codes  Xn
Risk Statements  22-40
Safety Statements  36/37
WGK Germany  2
RTECS  EL9085000
HS Code  2914500000

Nabumetone price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich N6142 Nabumetone analytical standard 42924-53-8 5g $121 2021-12-16 Buy
Sigma-Aldrich N0020000 Nabumetone European Pharmacopoeia (EP) Reference Standard 42924-53-8 $190 2021-12-16 Buy
Sigma-Aldrich BP358 Nabumetone British Pharmacopoeia (BP) Reference Standard 42924-53-8 $190 2021-12-16 Buy
Sigma-Aldrich 1449518 Nabumetone United States Pharmacopeia (USP) Reference Standard 42924-53-8 200mg $366 2021-12-16 Buy
Alfa Aesar J63072 Nabumetone 42924-53-8 25g $284 2021-12-16 Buy

Nabumetone Chemical Properties,Uses,Production

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.

Chemical Properties

White Powder

Originator

Beecham (United Kingdom)

Uses

Anti-inflammatory. Antibacterial.

Uses

anesthetic (local)

Uses

Anti-inflamatory. Antibacterial

Uses

Nabumetone is an anti-inflammatory and antibacterial agent (1). A non-steroidal anti-inflammatory prodrug used for treatment of inflammatory and degenerative rheumatic diseases.

Definition

ChEBI: A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration. It is s own to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs.

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.

Manufacturing Process

4-(5-Bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one
50 grams (0.179 moles) of 2-acetyl-5-bromo-6-methoxynaphthalene and 200 ml of n-butyl acetate are placed in a flask equipped with refrigerator and stirrer and, under stirring and at the temperature of 15°C, 14.5 g (0.268 moles) of sodium methoxide are added. The temperature of the reaction mixture goes up to 25°C and is kept at this value for 30 minutes, then the mixture is warmed at 65°C for one hour, is added with 100 ml of water and is brought to pH 4 by adding a concentrated aqueous solution of hydrochloric acid. The reaction mixture is then cooled to 0°-5°C and kept at this temperature for one hour. The solid is filtered, abundantly washed with water on the filter, then washed with butyl acetate and dried in oven under vacuum obtaining 53 g of product with a yield equal to 92%.
Example 1. 4-(6-Methoxy-2-naphthyl)butan-2-one
48 grams (0.150 moles) of 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut- 3-en-2-one, 6.1 g of sodium acetate hydrate containing 32.4% of water, equivalent to 0.050 moles of sodium acetate, 4 g of a 50% suspension in water of 10% palladium on carbon, equivalent to 0.0019 moles of palladium, and 500 ml of methanol are put in a hydrogenator. The hydrogenator is washed with nitrogen in order to eliminate the oxygen and then hydrogen is introduced at the pressure of 2 atmospheres. The temperature of reaction is kept at 40°C for a period of time of 6 hours, then the hydrogen is let off, the hydrogenator is washed with nitrogen and the reaction mixture is filtered to eliminate the catalyst. The solution is brought to pH 6 with a 5% aqueous solution of sodium hydroxide and concentrated under vacuum. The oily residue is dissolved into 130 ml of isopropanol and 30 ml of N,Ndimethylformamide and the solution is added with 45 ml of water and 17.6 g of sodium bisulfite obtaining a suspension that is stirred for one hour at 60°C, then is cooled to 5°C and is filtered. The obtained solid is washed with 75 ml of methanol, suspended in 200 ml of a 5% aqueous solution of sodium hydroxide and kept under stirring at room temperature for three hours. The suspension is then filtered, the solid is washed with water until neutrality and dried in oven under vacuum obtaining 18 g of product with a yield equal to 52.8%.
Example 2. 4-(6-Methoxy-2-naphthy)butan-2-one
The reaction described above is repeated with the sole changes of doubling the amount of sodium acetate hydrate containing 32.4% of water, 12.22 g equivalent to 0.100 moles of sodium acetate, and of lowering the hydrogenation time to five hours. In this way 22.5 g of product are obtained with a yield equal to 66%.
Example 3. 4-(6-Methoxy-2-naphthyl)butan-2-one
The reaction described in example 3 is repeated with the sole changes of nearly triplicating the amount of sodium acetate hydrate containing 32.4% of water, 17.60 g equivalent to 0.145 moles of sodium acetate, and of lowering the hydrogenation time to five hours. The oil obtained by evaporating the solvent at the end of the reaction is treated with 300 ml of toluene and 100 ml of water and after 15 minutes of stirring the two layers are separated. The aqueous phase is discarded while the organic phase is evaporated under vacuum at 70°C obtaining an oil that is dissolved into 100 ml of methanol. The solution is kept at 0°C for two hours and the precipitated solid is filtered, washed with 15 ml of methanol cooled to 0°C and dried in oven under vacuum. In this way 21.7 g of product are obtained. The methanolic filtrates from crystallization and washing are concentrated under vacuum to half volume so obtaining, after cooling to 0°C, the crystallization of other 4 g of product with an overall yield equal to 75.3%.

brand name

Relafen (Smith-Kline Beecham);RELIFEX.

Therapeutic Function

Antiinflammatory

General Description

Nabumetone (Relafen), a nonacidic NSAID prodrug, isclassified as an arylacetic acid, because it undergoes rapidhepatic metabolism to its active metabolite, 6-methoxy-2-naphthylacetic acid. Similar to the other arylacetic aciddrugs, it is used in short- or long-term management of RAand OA. Being nonacidic, it does not produce significantprimary insult to the GI mucosa lining and also has no effecton prostaglandin synthesis in gastric mucosa, thus producingminimum secondary GI damage when comparedwith other conventional NSAIDs.

Pharmacokinetics

Nabumetone is absorbed primarily from the duodenum. Milk and food increase the rate of absorption and the bioavailability of the active metabolite. Plasma concentrations of unchanged drug are too low to be detected in most subjects after oral administration, so most pharmacokinetic studies have involved the disposition of the active metabolite. Pharmacokinetic properties are altered in elderly patients, with higher plasma levels of the active metabolite being noted. Nabumetone undergoes rapid and extensive metabolism in the liver, with a mean absolute bioavailability of the active metabolite of 38%. The metabolism of nabumetone is illustrated in Figure 36.15. The major, most active metabolite is 6MNA, but the initial alcohol metabolite, a minor product, and its esters also possess significant anti-inflammatory properties.

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

Nabumetone synthesis

73356-31-7
42924-53-8
Synthesis of Nabumetone from 3-Buten-2-one, 4-hydroxy-4-(6-methoxy-2-naphthalenyl)-

Nabumetone Preparation Products And Raw materials

Raw materials

Preparation Products


Nabumetone Suppliers

Global( 229)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29954 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5941 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
Shaanxi Dideu Medichem Co. Ltd
13772537765
029-88380327 1010@dideu.com CHINA 3993 58
Zhuozhou Wenxi import and Export Co., Ltd
+8613111626072 (WhatsApp)
Wechat: +8613111626072 Wickr me: waynehu zzwenxi@126.com CHINA 13187 58
Fuxin Pharmaceutical
021-50872116
contact@fuxinpharm.com CHINA 10305 58
SHANGHAI T&W PHARMACEUTICAL CO., LTD.
86-021-61999440
contact@trustwe.com CHINA 10008 58

View Lastest Price from Nabumetone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-01 Nabumetone
42924-53-8
US $1.90 / KG 1KG 99% 10 ton Hebei Crovell Biotech Co Ltd
2021-07-20 Nabumetone
42924-53-8
US $1.00-1.00 / KG 1g 99% 50tons Shaanxi Dideu Medichem Co. Ltd
2021-07-13 Nabumetone
42924-53-8
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

42924-53-8(Nabumetone)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved