Nabumetone Chemical Properties
- Melting point:
- Boiling point:
- 330.1°C (rough estimate)
- 1.0657 (rough estimate)
- refractive index
- 1.5542 (estimate)
- storage temp.
- Soluble in alcohol or chloroform
- CAS DataBase Reference
- 42924-53-8(CAS DataBase Reference)
- NIST Chemistry Reference
Nabumetone Usage And Synthesis
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.
Beecham (United Kingdom)
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.
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.
Relafen (Smith-Kline Beecham);RELIFEX.
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.
- Nabumetone Ph.Eur
- NABUMETONE IMP. C (EP): (2RS)-4-(6-METHOXYNAPHTHALEN-2-YL)-BUTAN-2-OL
- 1,3,5(10), 6,8(14-BETA)-ESTRAPENTAEN-3-OL-17-ONE METHYL ETHER
- D-EQUILENIN ACETATE
- 1,3-Butanedione, 1-(6-methoxy-2-naphthalenyl)-
- D-1,3,5(10), 6,8-ESTRAPENTAEN-3-OL-17-ONE BENZYL ETHER
- 1,3,5(10), 6,8(14-BETA)-ESTRAPENTAEN-3-OL-17-ONE ACETATE
- D-1,3,5(10), 6,8-ESTRAPENTAEN-3-OL-17-ONE ETHYL ETHER
- D-1,3,5(10), 6,8-ESTRAPENTAEN-3-OL-17-ONE BENZOATE
- D-1,3,5(10), 6,8-ESTRAPENTAEN-3-OL-17-ONE METHYL ETHER
- m-Anisyl alcohol
- Methoxyacetic acid
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