CHEBI:7443 - nabumetone

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ChEBI Name nabumetone
ChEBI ID CHEBI:7443
Definition A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration. It is shown to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H16O2
Net Charge 0
Average Mass 228.28630
Monoisotopic Mass 228.115
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
InChIKey BLXXJMDCKKHMKV-UHFFFAOYSA-N
SMILES COc1ccc2cc(CCC(C)=O)ccc2c1
Roles Classification
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing nabumetone (CHEBI:7443) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
nabumetone (CHEBI:7443) has role non-narcotic analgesic (CHEBI:35481)
nabumetone (CHEBI:7443) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
nabumetone (CHEBI:7443) has role prodrug (CHEBI:50266)
nabumetone (CHEBI:7443) is a methoxynaphthalene (CHEBI:48851)
nabumetone (CHEBI:7443) is a methyl ketone (CHEBI:51867)
INNs Sources
nabumetona ChemIDplus
nabumetone KEGG DRUG
nabumetonum DrugBank
Synonyms Sources
4-(6-Methoxy-2-naphthalenyl)-2-butanone ChemIDplus
4-(6-Methoxy-2-naphthyl)-2-butanone ChemIDplus
Brand Name Source
Relafen KEGG DRUG
Manual Xrefs Databases
1863 DrugCentral
D00425 KEGG DRUG
DB00461 DrugBank
HMDB0014604 HMDB
LSM-3453 LINCS
Nabumetone Wikipedia
NBO PDBeChem
View more database links
Registry Numbers Types Sources
2103472 Beilstein Registry Number ChemIDplus
2103472 Reaxys Registry Number Reaxys
42924-53-8 CAS Registry Number NIST Chemistry WebBook
42924-53-8 CAS Registry Number KEGG DRUG
42924-53-8 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017