Compound: nabumetone
SMILES: O=C(CCc1cc2c(cc(OC)cc2)cc1)C
InChIKey: BLXXJMDCKKHMKV-UHFFFAOYSA-N
Synonyms: nabumetone, 42924-53-8, Relafen, 4-(6-methoxynaphthalen-2-yl)butan-2-one, Nabumetona, 4-(6-Methoxy-2-naphthyl)-2-butanone, nabumeton, Nabumetonum, BRL-14777, 4-(6-Methoxy-2-naphthalenyl)-2-butanone, 2-Butanone, 4-(6-methoxy-2-naphthalenyl)-, DTXSID4045472, LW0TIW155Z, NSC-758623, CHEBI:7443, DTXCID2025472, Nabumetone [USAN:USP:INN:BAN:JAN], ApoNabumetone, Rhoxal nabumetone, Nabumetone (USAN:USP:INN:BAN:JAN), Nabumetone 500 mg, Nabumetone 750 mg, RELAFEN DS, Nabumetone 1000 mg, RefChem:55684, M01AX01, 641-917-1, Arthaxan, Relifen, Relifex, Listran, Consolan, Balmox, Nabumetonum [INN-Latin], 4-(2-Methoxynaphthalen-6-yl)butan-2-one, Nabuser, BRL 14777, MFCD00079518, MLS000069541, BRL14777, Mebutan, Relif, SMR000058835, Dolsinal, Flambate, Unimetone, Prodac, 4-(6-methoxy-2-naphthyl)butan-2-one, NCGC00016853-01, CAS-42924-53-8, SR-01000759138, UNII-LW0TIW155Z, BRN 2103472, CCRIS 8108, Nabumetone CRS, Nabumatone Form II, Relafen (TN), Nabumetone (Standard), Spectrum_001486, NABUMETONE [MI], Opera_ID_765, NABUMETONE [INN], NABUMETONE [JAN], Prestwick0_000909, Prestwick1_000909, Prestwick2_000909, Prestwick3_000909, Spectrum2_001969, Spectrum4_000174, Spectrum5_001286, NABUMETONE [USAN], NABUMETONE [VANDF], cid_4409, NABUMETONE [MART.], SCHEMBL2256, CHEMBL1070, NABUMETONE [USP-RS], NABUMETONE [WHO-DD], BSPBio_000758, KBioGR_000687, KBioSS_001966, MLS001076325, BIDD:GT0104, DivK1c_000850, SPECTRUM1503650, SPBio_002097, SPBio_002957, Nabumetone, analytical standard, BPBio1_000834, GTPL7245, Nabumetone (JP17/USP/INN), Nabumetone - Bio-X trade mark, orb1309207, orb3025300, NABUMETONE [ORANGE BOOK], SCHEMBL18096515, SCHEMBL29373228, SCHEMBL29570823, BDBM40128, HMS502K12, HY-B0559R, KBio1_000850, KBio2_001966, KBio2_004534, KBio2_007102, MSK7165, NABUMETONE [EP MONOGRAPH], NABUMETONE [USP IMPURITY], NINDS_000850, HMS1570F20, HMS1922G10, HMS2090D13, HMS2093I05, HMS2097F20, HMS2230H12, HMS3259I16, HMS3652M04, HMS3714F20, HMS3885A22, HMS5082E04, NABUMETONE [USP MONOGRAPH], Pharmakon1600-01503650, HY-B0559, Tox21_110647, CCG-39507, EBC-26251, NSC758623, s4051, AKOS009529199, MSK7165-1000A, Tox21_110647_1, DB00461, FN26115, KS-1371, NC00579, NSC 758623, IDI1_000850, NCGC00016853-02, NCGC00016853-03, NCGC00016853-06, NCGC00016853-13, NCGC00095063-01, NCGC00095063-02, AC-19025, BN166181, 1-(2'-Methoxynaphth-6'-yl)butan-3-one, SBI-0051869.P002, AB00052392, NS00003590, SW197312-3, D00425, L10109, AB00052392-13, AB00052392_14, AB00052392_15, EN300-1853581, Nabumetone Solution in Acetonitrile, 1000ug/mL, F211337, Q425207, SR-01000759138-2, SR-01000759138-3, BRD-K65146499-001-04-8, BRD-K65146499-001-14-7, BRD-K65146499-001-26-1, BRD-K65146499-001-27-9, Nabumetone, British Pharmacopoeia (BP) Reference Standard, Nabumetone, European Pharmacopoeia (EP) Reference Standard, Nabumetone, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C15H16O2
molecular_weight: 228.29 g/mol
exact_mass: 228.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 17
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 78-82
solubility: Practically insoluble
Descriptions:
{"pubchem": "Nabumetone is 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. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a prodrug and a cyclooxygenase 2 inhibitor. It is a methoxynaphthalene and a methyl ketone.", "chebi": "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.", "chembl": "NABUMETONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "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.\nNabumetone 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.\nIn 2023, it was the 271st most commonly prescribed medication in the United States, with more than 800,000 prescriptions."}