U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C15H16O2
Molecular Weight 228.2863
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NABUMETONE

SMILES

COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2

InChI

InChIKey=BLXXJMDCKKHMKV-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Nabumetone is a naphthylalkanone. Is is a non-selective prostaglandin G/H synthase (a.k.a. cyclooxygenase or COX) inhibitor that acts on both prostaglandin G/H synthase 1 and 2 (COX-1 and -2). Prostaglandin G/H synthase catalyzes the conversion of arachidonic acid to prostaglandin G2 and prostaglandin G2 to prostaglandin H2. Prostaglandin H2 is the precursor to a number of prostaglandins involved in fever, pain, swelling, inflammation, and platelet aggregation. The parent compound is a prodrug that undergoes hepatic biotransformation to the active compound, 6-methoxy-2-naphthylacetic acid (6MNA). The analgesic, antipyretic and anti-inflammatory effects of NSAIDs occur as a result of decreased prostaglandin synthesis. The parent compound is a prodrug, which undergoes hepatic biotransformation to the active component, 6-methoxy-2-naphthylacetic acid (6MNA), that is a potent inhibitor of prostaglandin synthesis, most likely through binding to the COX-2 and COX-1 receptors. Nabumetone is used for acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex, and Gambaran.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
149.0 µM [IC50]
230.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nabumetone
Primary
Nabumetone

Cmax

ValueDoseCo-administeredAnalytePopulation
13.48 ng/mL
1000 mg single, oral
NABUMETONE plasma
Homo sapiens
21.9 μg/mL
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
33.7 μg/mL
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
52.3 μg/mL
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
66.7 μg/mL
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
204.98 ng × h/mL
1000 mg single, oral
NABUMETONE plasma
Homo sapiens
1120 μg × h/mL
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
2150 μg × h/mL
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
1022 μg × h/mL
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
1270 μg × h/mL
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.82 h
1000 mg single, oral
NABUMETONE plasma
Homo sapiens
26.3 h
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
38.8 h
1000 mg single, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
27.5 h
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
34.2 h
1000 mg 1 times / day steady-state, oral
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens

Doses

AEs

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Initial dose: 1000 mg orally once a day Maintenance dose: 1500 to 2000 mg orally per day in 1 or 2 divided doses Maximum dose: 2000 mg/day
Route of Administration: Oral
In Vitro Use Guide
Nabumetone (50 ug/ml) was found to significantly increase COX-2 at mRNA levels but directly suppress the concentration of PGE2 in culture medium of human intervertebral disc cells.