Product Name

Nabumetone

CAS Number

42924-53-8

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Product Name:
Nabumetone
CAS Number:
42924-53-8
Indication:
For acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis.
Mode of Action:

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.

Pharmacodynamics:

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.

Metabolism:

Undergoes rapid biotransformation to the principal active metabolite, 6-methoxy-2-naphthylacetic acid (6MNA). Approximately 35% of a 1000 mg oral dose of nabumetone is converted to 6MNA and 50% is converted into unidentified metabolites which are subsequently excreted in the urine.

Toxicity:

The one overdose occurred in a 17-year-old female patient who had a history of abdominal pain and was hospitalized for increased abdominal pain following ingestion of 30 nabumetone tablets (15 grams total). Stools were negative for occult blood and there was no fall in serum hemoglobin concentration. The patient had no other symptoms.

IUPAC:
4-(6-methoxynaphthalen-2-yl)butan-2-one
ATC:
M01AX01
PubChem:
4409
DrugBank:
DB00461 (APRD01128)
Formula:
C12H12N2O3
Molecular Mass:
228.2863
Synonyms:
Nabumetona Nabumetonum [INN-Latin]
SMILES:
COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2
AHFS Code:
28:08.04.92
InChi:
BLXXJMDCKKHMKV-UHFFFAOYSA-N

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