Nabumetone | CAS#42924-53-8

Nabumetone
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318296

CAS#: 42924-53-8

Description: Nabumetone is a non-steroidal anti-inflammatory drug (NSAID), the only 1-naphthaleneacetic acid derivative. It is a nonacidic NSAID that is rapidly metabolized in the liver to a major active metabolite, 6-methoxy-2-naphthyl acetic acid. As found with previous NSAIDs, nabumetone's active metabolite inhibits the cyclooxygenase enzyme and preferentially blocks COX-2 activity (which is indirectly responsible for the production of inflammation and pain during arthritis). The active metabolite of nabumetone is felt to be the compound primarily responsible for therapeutic effect. Comparatively, the parent drug is a poor inhibitor of COX-2 byproducts, particularly prostaglandins. It may be less nephrotoxic than indomethacin.

Chemical Structure

Nabumetone

CAS# 42924-53-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318296
Name: Nabumetone
CAS#: 42924-53-8
Chemical Formula: C15H16O2
Exact Mass: 228.12
Molecular Weight: 228.286
Elemental Analysis: C, 78.92; H, 7.06; O, 14.02

Price and Availability

Size	Price	Availability
1g	USD 250	2 weeks
5g	USD 550	2 weeks
10g	USD 750	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

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Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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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.

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