Nabumetone

Nabumetone
Clinical data
Trade names	Relafen
AHFS/Drugs.com	Monograph
MedlinePlus	a692022
License data	US DailyMed: Nabumetone;
Routes of; administration	By mouth
ATC code	M01AX01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: WARNING;
Pharmacokinetic data
Protein binding	> 99% (active metabolite)
Metabolism	Liver, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA
Elimination half-life	23 hours (active metabolite)
Excretion	Kidney
Identifiers
	IUPAC name 4-(6-methoxy-2-naphthyl)-2-butanone;
CAS Number	42924-53-8 ;
PubChem CID	4409;
IUPHAR/BPS	7245;
DrugBank	DB00461 ;
ChemSpider	4256 ;
UNII	LW0TIW155Z;
KEGG	D00425 ;
ChEBI	CHEBI:7443 ;
ChEMBL	ChEMBL1070 ;
CompTox Dashboard (EPA)	DTXSID4045472 ;
ECHA InfoCard	100.169.752
Chemical and physical data
Formula	C15H16O2
Molar mass	228.291 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(C)CCc1ccc2c(c1)ccc(OC)c2;
	InChI 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 ; Key:BLXXJMDCKKHMKV-UHFFFAOYSA-N ;
	(what is this?) (verify)

Nabumetone, sold under the brand name Relafen among others, is a nonsteroidal anti-inflammatory drug (NSAID).^[3] Nabumetone was developed by Beecham and first received regulatory approval in 1991.^[4]

Nabumetone is a non-acidic NSAID prodrug that is rapidly metabolized in the liver to the active metabolite, 6-methoxy-2-naphthyl acetic acid. 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.^[5] There are two known polymorphs of the compound.^[6] Nabumetone has little effect on renal prostaglandin secretion and less of an association with heart failure than other traditional drugs of the class.^[7] Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors are also good,^{[clarification needed]} equivalent to paracetamol.^[8]

In 2021, it was the 250th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[9]^[10]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ Varfaj F, Zulkifli SN, Park HG, Challinor VL, De Voss JJ, Ortiz de Montellano PR (May 2014). "Carbon-carbon bond cleavage in activation of the prodrug nabumetone". Drug Metabolism and Disposition. 42 (5): 828–838. doi:10.1124/dmd.114.056903. PMC 3989788. PMID 24584631.
^ Gonzalo-Garijo MA, Cordobés-Duran C, Lamilla-Yerga AM, Moreno-Gastón I (2007). "Severe immediate reaction to nabumetone". Journal of Investigational Allergology & Clinical Immunology. 17 (4): 274–276. PMID 17694703.
^ "Nabumetone Page". RCSB Protein Data Bank. Retrieved 5 August 2021.
^ Olsen NV, Jensen NG, Hansen JM, Christensen NJ, Fogh-Andersen N, Kanstrup IL (October 1999). "Non-steroidal anti-inflammatory drugs and renal response to exercise: a comparison of indomethacin and nabumetone". Clinical Science. 97 (4): 457–465. doi:10.1042/cs0970457. PMID 10491346. S2CID 33526598.
^ Price CP, Grzesiak AL, Lang M, Matzger AJ (2002). "Polymorphism of Nabumetone". Crystal Growth & Design. 2 (6): 501–503. doi:10.1021/cg0255568.
^ Donnan PT (2000). "098. A Drug-Safety Study to Examine the Possible Association of Congestive Heart Failure with Dispensed Nabumetone, Ibuprofen and other Non-Steroidal Anti-inflammatory Drugs". Pharmacoepidemiology and Drug Safety. 8 (S2): S115. doi:10.1002/(SICI)1099-1557(199908)8:2+<S79::AID-PDS429>3.0.CO;2-2.
^ Palmer RH, Haig AE, Flavin SK, Iyengar MK (2001). "Effects of ibuprofen (IB), nabumetone (N) and celecoxib (C) on blood pressure (BP) control in hypertensive patients on ACE inhibitors". American Journal of Hypertension. 14 (S1): 85A. doi:10.1016/S0895-7061(01)01811-8.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Nabumetone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[2] Varfaj F, Zulkifli SN, Park HG, Challinor VL, De Voss JJ, Ortiz de Montellano PR (May 2014). "Carbon-carbon bond cleavage in activation of the prodrug nabumetone". Drug Metabolism and Disposition. 42 (5): 828–838. doi:10.1124/dmd.114.056903. PMC 3989788. PMID 24584631.

[pmid17694703-3] Gonzalo-Garijo MA, Cordobés-Duran C, Lamilla-Yerga AM, Moreno-Gastón I (2007). "Severe immediate reaction to nabumetone". Journal of Investigational Allergology & Clinical Immunology. 17 (4): 274–276. PMID 17694703.

[4] "Nabumetone Page". RCSB Protein Data Bank. Retrieved 5 August 2021.

[5] Olsen NV, Jensen NG, Hansen JM, Christensen NJ, Fogh-Andersen N, Kanstrup IL (October 1999). "Non-steroidal anti-inflammatory drugs and renal response to exercise: a comparison of indomethacin and nabumetone". Clinical Science. 97 (4): 457–465. doi:10.1042/cs0970457. PMID 10491346. S2CID 33526598.

[6] Price CP, Grzesiak AL, Lang M, Matzger AJ (2002). "Polymorphism of Nabumetone". Crystal Growth & Design. 2 (6): 501–503. doi:10.1021/cg0255568.

[7] Donnan PT (2000). "098. A Drug-Safety Study to Examine the Possible Association of Congestive Heart Failure with Dispensed Nabumetone, Ibuprofen and other Non-Steroidal Anti-inflammatory Drugs". Pharmacoepidemiology and Drug Safety. 8 (S2): S115. doi:10.1002/(SICI)1099-1557(199908)8:2+<S79::AID-PDS429>3.0.CO;2-2.

[8] Palmer RH, Haig AE, Flavin SK, Iyengar MK (2001). "Effects of ibuprofen (IB), nabumetone (N) and celecoxib (C) on blood pressure (BP) control in hypertensive patients on ACE inhibitors". American Journal of Hypertension. 14 (S1): 85A. doi:10.1016/S0895-7061(01)01811-8.

[9] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[10] "Nabumetone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]