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Nabumetone
NSAID analgesic and anti-inflammatory drug
NSAID analgesic and anti-inflammatory drug
| Field | Value | ||
|---|---|---|---|
| Verifiedfields | changed | ||
| verifiedrevid | 462258056 | ||
| image | Nabumetone.svg | ||
| image_class | skin-invert-image | ||
| tradename | Relafen | ||
| Drugs.com | |||
| MedlinePlus | a692022 | ||
| DailyMedID | Nabumetone | ||
| pregnancy_AU | |||
| routes_of_administration | By mouth | ||
| ATC_prefix | M01 | ||
| ATC_suffix | AX01 | ||
| legal_AU | S4 | ||
| legal_BR | |||
| legal_CA | |||
| legal_DE | |||
| legal_NZ | |||
| legal_UK | POM | ||
| legal_US | Rx-only | ||
| legal_US_comment | |||
| legal_UN | |||
| legal_status | |||
| protein_bound | 99% (active metabolite) | ||
| metabolism | Liver, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA | ||
| elimination_half-life | 23 hours (active metabolite) | ||
| excretion | Kidney | ||
| CAS_number_Ref | |||
| CAS_number | 42924-53-8 | ||
| PubChem | 4409 | ||
| IUPHAR_ligand | 7245 | ||
| DrugBank_Ref | |||
| DrugBank | DB00461 | ||
| ChemSpiderID_Ref | |||
| ChemSpiderID | 4256 | ||
| UNII_Ref | |||
| UNII | LW0TIW155Z | ||
| KEGG_Ref | |||
| KEGG | D00425 | ||
| ChEBI_Ref | |||
| ChEBI | 7443 | ||
| ChEMBL_Ref | |||
| ChEMBL | 1070 | ||
| IUPAC_name | 4-(6-methoxy-2-naphthyl)-2-butanone | ||
| C | 15 | H=16 | O=2 |
| SMILES | O=C(C)CCc1ccc2c(c1)ccc(OC)c2 | ||
| StdInChI_Ref | |||
| StdInChI | 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 | ||
| StdInChIKey_Ref | |||
| StdInChIKey | BLXXJMDCKKHMKV-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life = 23 hours (active metabolite)
Nabumetone, sold under the brand name Relafen among others, is a nonsteroidal anti-inflammatory drug (NSAID). Nabumetone was developed by Beecham and first received regulatory approval in 1991.
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. There are two known polymorphs of the compound. Nabumetone has little effect on renal prostaglandin secretion and less of an association with heart failure than other traditional drugs of the class. Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors are also good, equivalent to paracetamol.
In 2023, it was the 271st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.
Medical uses
Nabumetone is indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis.
Side effects
Side effects include bloody or black, tarry stools; change in color, frequency, or amount of urine; chest pain; shortness of breath; coughing up blood; pale stools; numbness; weakness; flu-like symptoms; leg pain; vision problems; speech problems; problems walking; weight gain; stomach pain; cold sweat; skin rash; blisters; headache; swelling; bleeding; bruising; vomiting blood; jaundice; diarrhea; constipation; dizziness; indigestion; gas; nausea; and ringing in the ears.
In October 2020, the US Food and Drug Administration (FDA) required the prescribing information to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.
Society and culture
Brand names
It is sold under many brand names, including Relafen, Relifex, and Gambaran.
References
References
- (15 July 2021). "Relafen- nabumetone tablet".
- (8 January 2024). "Relafen DS- nabumetone tablet".
- (May 2014). "Carbon-carbon bond cleavage in activation of the prodrug nabumetone". Drug Metabolism and Disposition.
- (2007). "Severe immediate reaction to nabumetone". Journal of Investigational Allergology & Clinical Immunology.
- "Nabumetone Page". RCSB Protein Data Bank.
- (October 1999). "Non-steroidal anti-inflammatory drugs and renal response to exercise: a comparison of indomethacin and nabumetone". Clinical Science.
- (2002). "Polymorphism of Nabumetone". Crystal Growth & Design.
- (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.
- (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.
- "The Top 300 of 2023".
- "Nabumetone Drug Usage Statistics, United States, 2014 - 2023".
- "Relafen (Nabumetone): Side Effects, Interactions, Warning, Dosage & Uses". RxList.
- (15 October 2020). "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications".
- (21 July 2017). "NSAIDs may cause rare kidney problems in unborn babies".
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