Related CAS #
65726-24-1 (alcohol)
42924-53-8 (free)
Synonym
Nabumetone, Relafen, Relifex, Gambaran, Arthraxan, BRL 14777
IUPAC/Chemical Name
4-(6-methoxynaphthalen-2-yl)butan-2-one
InChi Key
BLXXJMDCKKHMKV-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CC(CCC1=CC=C2C=C(OC)C=CC2=C1)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Nabumetone is an orally active non-acidic anti-inflammatory agent, acts as a potent and selective COX-2 inhibitor, and is the prodrug of the active metabolite 6MNA.
In vitro activity:
In this study, a potent COX2 inhibitor, nabumetone (NBT), was investigated for its anti-proliferative and apoptotic effects in K-562 and Meg-01 chronic myeloid leukemia blastic cell lines as a single agent or in combination with adriamycin (ADR) and interferon alpha (IFN-a). In these cell lines, a dose-dependent inhibition of proliferation was observed with NBT.
Reference: Leuk Lymphoma. 2005 May;46(5):753-6. https://pubmed.ncbi.nlm.nih.gov/16019514/
In vivo activity:
6MNA, the active metabolite of the non-acidic anti-inflammatory drug nabumetone, was investigated using intravenous administration for effects on (a) carrageenan paw oedema and gastric irritancy compared to either oral nabumetone or both oral and intravenous indomethacin when given acutely and (b) gastrointestinal irritancy when given in repeat dosing studies. An oral dose of nabumetone or intravenous 6MNA produced effective anti-inflammatory activity together with significant inhibition of paw exudate PGE2. An anti-inflammatory oral dose of nabumetone or intravenous 6MNA produced minimal effects on gastric 6-keto-PGF1 alpha production, with an absence of gastric damage, in contrast to indomethacin.
Reference: Agents Actions. 1992;Spec No:C82-3. https://pubmed.ncbi.nlm.nih.gov/1442340/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
131.41 |
| DMSO |
58.7 |
256.99 |
| DMSO:PBS (pH 7.2) (1:10) |
0.1 |
0.39 |
| Ethanol |
22.5 |
98.56 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
228.29
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Qureshi S, Chandra S, Chopra D, Dubey D, Jain V, Roy SK, Ray RS. Nabumetone induced photogenotoxicity mechanism mediated by ROS generation under environmental UV radiation in human keratinocytes (HaCaT) cell line. Toxicol Appl Pharmacol. 2021 Jun 1;420:115516. doi: 10.1016/j.taap.2021.115516. Epub 2021 Mar 30. PMID: 33798594.
2. Vural F, Ozcan MA, Ozsan GH, Ateş H, Demirkan F, Pişkin O, Undar B. Cyclo-oxygenase 2 inhibitor, nabumetone, inhibits proliferation in chronic myeloid leukemia cell lines. Leuk Lymphoma. 2005 May;46(5):753-6. doi: 10.1080/10428190400027860. PMID: 16019514.
3. Roy HK, Karolski WJ, Wali RK, Ratashak A, Hart J, Smyrk TC. The nonsteroidal anti-inflammatory drug, nabumetone, differentially inhibits beta-catenin signaling in the MIN mouse and azoxymethane-treated rat models of colon carcinogenesis. Cancer Lett. 2005 Jan 20;217(2):161-9. doi: 10.1016/j.canlet.2004.07.042. PMID: 15617833.
4. Melarange R, Gentry C, O'Connell C, Blower PR, Neil C, Kelvin AS, Toseland CD. Anti-inflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6MNA (6-methoxy-2-naphthylacetic acid): comparison with indomethacin. Agents Actions. 1992;Spec No:C82-3. PMID: 1442340.
In vitro protocol:
1. Qureshi S, Chandra S, Chopra D, Dubey D, Jain V, Roy SK, Ray RS. Nabumetone induced photogenotoxicity mechanism mediated by ROS generation under environmental UV radiation in human keratinocytes (HaCaT) cell line. Toxicol Appl Pharmacol. 2021 Jun 1;420:115516. doi: 10.1016/j.taap.2021.115516. Epub 2021 Mar 30. PMID: 33798594.
2. Vural F, Ozcan MA, Ozsan GH, Ateş H, Demirkan F, Pişkin O, Undar B. Cyclo-oxygenase 2 inhibitor, nabumetone, inhibits proliferation in chronic myeloid leukemia cell lines. Leuk Lymphoma. 2005 May;46(5):753-6. doi: 10.1080/10428190400027860. PMID: 16019514.
In vivo protocol:
1. Roy HK, Karolski WJ, Wali RK, Ratashak A, Hart J, Smyrk TC. The nonsteroidal anti-inflammatory drug, nabumetone, differentially inhibits beta-catenin signaling in the MIN mouse and azoxymethane-treated rat models of colon carcinogenesis. Cancer Lett. 2005 Jan 20;217(2):161-9. doi: 10.1016/j.canlet.2004.07.042. PMID: 15617833.
2. Melarange R, Gentry C, O'Connell C, Blower PR, Neil C, Kelvin AS, Toseland CD. Anti-inflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6MNA (6-methoxy-2-naphthylacetic acid): comparison with indomethacin. Agents Actions. 1992;Spec No:C82-3. PMID: 1442340.
1: Moore RA, Derry S, Moore M, McQuay HJ. Single dose oral nabumetone for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD007548. doi: 10.1002/14651858.CD007548.pub2. Review. PubMed PMID: 19821428; PubMed Central PMCID: PMC4170900.
2: Starek M, Krzek J. A review of analytical techniques for determination of oxicams, nimesulide and nabumetone. Talanta. 2009 Jan 15;77(3):925-42. doi: 10.1016/j.talanta.2008.09.022. Epub 2008 Sep 24. Review. PubMed PMID: 19064072.
3: Bannwarth B. Safety of the nonselective NSAID nabumetone : focus on gastrointestinal tolerability. Drug Saf. 2008;31(6):485-503. Review. PubMed PMID: 18484783.
4: Hedner T, Samulesson O, Währborg P, Wadenvik H, Ung KA, Ekbom A. Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs. 2004;64(20):2315-43; discussion 2344-5. Review. PubMed PMID: 15456329.
5: Davies NM, McLachlan AJ. [Properties and features of nabumetone]. Drugs. 2000;59 Spec No 1:25-33. Review. French. PubMed PMID: 10841070.
6: Davies NM. Clinical pharmacokinetics of nabumetone. The dawn of selective cyclo-oxygenase-2 inhibition? Clin Pharmacokinet. 1997 Dec;33(6):404-16. Review. PubMed PMID: 9435990.
7: Hilleman DE, Mohiuddin SM, Lucas BD Jr. Nonsteroidal antiinflammatory drug use in patients receiving warfarin: emphasis on nabumetone. Am J Med. 1993 Aug 9;95(2A):30S-34S. Review. PubMed PMID: 8357000.
8: Roth SH. Upper gastrointestinal safety with nabumetone. J Rheumatol Suppl. 1992 Nov;36:74-9. Review. PubMed PMID: 1474539.
9: Bernhard GC. Worldwide safety experience with nabumetone. J Rheumatol Suppl. 1992 Nov;36:48-57. Review. PubMed PMID: 1474535.
10: Hyneck ML. An overview of the clinical pharmacokinetics of nabumetone. J Rheumatol Suppl. 1992 Nov;36:20-4. Review. PubMed PMID: 1474531.
11: Blower PR. The unique pharmacologic profile of nabumetone. J Rheumatol Suppl. 1992 Nov;36:13-9. Review. PubMed PMID: 1474529.
12: Nabumetone (Relifex)--another NSAID. Drug Ther Bull. 1988 May 31;26(11):41-3. Review. Erratum in: Drug Ther Bull 1988 Aug 22;26(17):68. PubMed PMID: 3289871.
13: Friedel HA, Todd PA. Nabumetone. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in rheumatic diseases. Drugs. 1988 May;35(5):504-24. Review. PubMed PMID: 3293969.
14: Roth SH. [Rationale for using nabumetone and clinical experience]. Drugs. 2000;59 Spec No 1:35-41. Review. French. PubMed PMID: 10841071.
15: Nasonov EL, Nasonova SV. [Nabumetone, a new nonsteroidal antiinflammatory agent: clinical prospects]. Klin Med (Mosk). 1996;74(8):13-6. Review. Russian. PubMed PMID: 9036198.
16: Simón M, Sádaba B, Honorato J. [Nabumetone]. Rev Med Univ Navarra. 1995 Jul-Sep;39(3):164-72. Review. Spanish. PubMed PMID: 8552919.
17: Helfgott SM. Nabumetone: a clinical appraisal. Semin Arthritis Rheum. 1994 Apr;23(5):341-6. Review. PubMed PMID: 8036523.
18: Dahl SL. Nabumetone: a "nonacidic" nonsteroidal antiinflammatory drug. Ann Pharmacother. 1993 Apr;27(4):456-63. Review. PubMed PMID: 8477124.
19: Aronoff GR. Therapeutic implications associated with renal studies of nabumetone. J Rheumatol Suppl. 1992 Nov;36:25-31. Review. PubMed PMID: 1474532.
20: Roth SH. Nabumetone: a new NSAID for rheumatoid arthritis and osteoarthritis. Orthop Rev. 1992 Feb;21(2):223-7. Review. PubMed PMID: 1538889.
