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

• ChemBase编号: 344
• 分子式: C15H16O2
• 平均质量: 228.28634
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-(6-methoxynaphthalen-2-yl)butan-2-one
• IUPAC传统名: nabumetone
• 商标名: Arthaxan; Balmox; Consolan; Dolsinal; Flambate; Listran; Mebutan; Nabuser; Prodac; Relafen; Relif; Relifen; Relifex; Unimetone
• 别名: 4-(6-甲氧基-2-萘基)-2-丁酮; 萘丁美酮; Nabumetonum [INN-Latin]; Nabumetona; Nabumetone; 4-(6-Methoxy-2-naphthyl)-2-butanone; Nabumetone; Arthaxan; Relafen

登记号

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

理论计算性质

ALOGPS 2.1

• Log P: 3.41
• LOG S: -5.07
• 溶解度: 1.93e-03 g/l

JChem

• Log P: 3.2169938
• 摩尔折射率: 68.4311 cm^3
• 极化性: 27.843512 Å^3
• 极化表面积: 26.3 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true
• Acid pKa: 19.59154
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.2169938
• LogD (pH = 7.4): 3.2169938

分子性质

理化性质

• 溶解度: Practically insoluble
• 疏水性(logP): 3.1

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: EL9085000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: COX
• 相关基因信息: human ... PTGS1(5742), PTGS2(5743)

产品相关信息

• 级别: analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C15H16O2

详细说明

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
非选择性非甾体抗炎药 (NSAID)