4-(6-methoxynaphthalen-2-yl)butan-2-one

• ChemBase ID: 344
• Molecular Formular: C15H16O2
• Molecular Mass: 228.28634
• Monoisotopic Mass: 228.11502975
• SMILES: O(c1cc2c(cc(CCC(=O)C)cc2)cc1)C
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)CCC(=O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(6-methoxynaphthalen-2-yl)butan-2-one
• IUPAC Traditional name: nabumetone
• Brand Name: Arthaxan; Balmox; Consolan; Dolsinal; Flambate; Listran; Mebutan; Nabuser; Prodac; Relafen; Relif; Relifen; Relifex; Unimetone
• Synonyms: Nabumetonum [INN-Latin]; Nabumetona; Nabumetone; 4-(6-Methoxy-2-naphthyl)-2-butanone; Nabumetone; Arthaxan; Relafen; 4-(6-甲氧基-2-萘基)-2-丁酮; 萘丁美酮

Database IDs

• CAS Number: 42924-53-8
• MDL Number: MFCD00079518
• PubChem SID: 24897772; 160963807; 46507729
• PubChem CID: 4409

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: 3.41
• LOG S: -5.07
• Solubility (Water): 1.93e-03 g/l

JChem

• Log P: 3.2169938
• Molar Refractivity: 68.4311 cm^3
• Polarizability: 27.843512 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 19.59154
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2169938
• LogD (pH = 7.4): 3.2169938

PROPERTIES

Physical Property

• Solubility: Practically insoluble
• Hydrophobicity(logP): 3.1

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: EL9085000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: COX
• Gene Information: human ... PTGS1(5742), PTGS2(5743)

Product Information

• Grade: analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H16O2

DETAILS

DrugBank - DB00461

• Drug Groups: approved
• Description: Nabumetone is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid family (which includes diclofenac). Marketed under the brand name Relafen, it has been shown to have a slightly lower risk of gastrointestinal side effects than most other non-selective NSAIDs.
• Indication: For acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis.
• Pharmacology: 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.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Well absorbed from the gastrointestinal tract. Coadministration of food increases the rate of absorption and subsequent appearance of 6MNA (the active metabolite) in the plasma but does not affect the extent of conversion of nabumetone into 6MNA.
• Half Life: Approximately 23 hours for the active metabolite, 6MNA. Increased in patients with renal insufficiency.
• Protein Binding: The active metabolite, 6MNA, is more than 99% bound to plasma proteins.
• Elimination: 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.
• Clearance: * 20 - 30 mL/min
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N6142

Biochem/physiol Actions
Nonselective non-steroidal anti-inflammatory drug (NSAID)