nabumetone
nabumetone
CAS: 42924-53-8
Molecular Formula: C15H16O2
nabumetone - Names and Identifiers
| Name | nabumetone |
| Synonyms | RELAFEN relifex Nabumeton brl147777 NABUMETONE nabumetone 4-(6-methoxy-2-naphthalenyl)-2-butanon 4-(6-methoxy-2-naphthalenyl)-2-butanone 4-(6-methoxynaphthalen-2-yl)butan-2-one methyl 3-(6-methoxynaphthalen-2-yl)propanoate NABUMETONE, IMPURITY F6,6'-DIMETHOXY-2,2'-BINAPHTHALENYL EP STANDARD |
| CAS | 42924-53-8 |
| EINECS | 611-790-7 |
| InChI | InChI=1/C15H16O3/c1-17-14-7-6-12-9-11(3-5-13(12)10-14)4-8-15(16)18-2/h3,5-7,9-10H,4,8H2,1-2H3 |
nabumetone - Physico-chemical Properties
| Molecular Formula | C15H16O2 |
| Molar Mass | 228.29 |
| Density | 1.0657 (rough estimate) |
| Melting Point | 80-810C |
| Boling Point | 330.1°C (rough estimate) |
| Flash Point | 156.1°C |
| Water Solubility | 6mg/L(22.5 ºC) |
| Solubility | Soluble in alcohol or chloroform |
| Vapor Presure | 9.69E-06mmHg at 25°C |
| Appearance | White to white-like solid |
| Color | White |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.5542 (estimate) |
| Use | Has anti-inflammatory, analgesic, antipyretic effect, for the treatment of rheumatism |
nabumetone - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 2 |
| RTECS | EL9085000 |
| HS Code | 2914500000 |
nabumetone - Upstream Downstream Industry
nabumetone - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| background and overview | rheumatoid arthritis (rheumatoid arthritis,RA) is a rheumatic disease with high incidence. its clinical features are mainly joint swelling and pain. due to the unknown pathogenesis and mechanism, the current treatment aims to relieve symptoms and protect joint function. Non-steroidal anti-inflammatory drugs (nonsteroid anti-inflammatory drugs,NSAIDs) are the most commonly used drugs for the treatment of rheumatoid arthritis (RA) and other arthritis diseases, which can relieve joint pain and reduce joint inflammation. However, due to many adverse reactions, especially the adverse reactions of gastrointestinal tract, the long-term application of this kind of drugs is limited. VANE et al. first realized that the anti-inflammatory effect and adverse reactions of NSAIDs are all due to the inhibition of cyclooxygenase (cyclooxygenase,COX). COX has COX-1 and COX-2 isoenzymes. COX-2 is an enzyme associated with inflammation and disease, while COX-1 is associated with gastrointestinal protection and platelet aggregation. Inhibition of COX-1 can lead to NSAIDs toxicity, so more drugs that specifically inhibit COX-2 and relatively less inhibit COX-1 should be safer. nabumetone (Nobumetone), also known as naphthalenone, rilifene, nabimetone, nabimetone, nabimetone, is a long-acting non-steroidal anti-inflammatory analgesic developed by the British Beecham company. It is a prodrug with a ketone structure. It can be metabolized into 6-methoxy-2-naphthalene acetic acid in the liver. The active metabolite has no hepatic and enteric circulation, and is almost all excreted in the urine and has strong anti-inflammatory activity, it is easy to be absorbed by oral administration, and has little gastrointestinal irritation, few adverse reactions and good tolerance. Mainly used for rheumatism, rheumatoid arthritis, osteoarthritis, soft tissue injury, ankylosing spondylitis; it has an inhibitory effect on prostaglandin synthase; the drug was launched in Ireland in 1985. Its good safety is mainly based on two factors: First, unlike acidic NSAIDs, nabumetone is a non-acidic prodrug, which has no direct toxic effect on the gastrointestinal mucosa after absorption in the duodenum; secondly, nabumetone is The active ingredient 6-MNA after the first-pass effect metabolism of the liver is secreted by the bile meter, no longer enters the hepatocutouinal circulation, and is almost completely excreted in the urine. Nabumetone is an effective, safe and convenient NSAIDs for RA and other arthritis diseases, which is worthy of clinical application. |
| trait | is white or almost white crystalline powder. Insoluble in water, slightly soluble in ethanol and methanol, easily soluble in acetone. |
| pharmacological action | is a prodrug of long-acting non-steroidal anti-inflammatory drugs. it is a non-acidic and non-ionic prodrug, mainly used for the treatment of symptoms of acute and chronic osteoarthritis and rheumatoid arthritis. The mechanism of action may be the same as other non-steroidal anti-inflammatory drugs. It acts on oxidase and inhibits the synthesis of prostaglandins. After oral absorption, it is biotransformed into the active compound 6-methoxy-2-naphthaleneacetic acid (6MNA) in the liver. It is a strong inhibitor of prostate biosynthesis. Its anti-inflammatory effect is significantly stronger than aspirin and fenbufen. It is far less irritating to the stomach than naproxen, indomethacin and aspirin. It has little effect on platelets and bleeding time, the incidence of gastrointestinal mucosal erosion and gastric hemorrhage is low. |
| clinical evaluation | 76 patients with rheumatoid arthritis were divided into 2 groups, 46 patients in nabumetone group, 14 males and 32 females, aged (45±11) years (22-68 years). nabumetone tablets were given 1g,po,qd× 4 weeks. In diclofenac group, 30 cases, 6 males and 24 females, aged (44±10) years (26-64 years) were given diclofenac 50 mg,po,qd× 4 weeks. Results: the total effective rate of nabumetone group was 91%, which was significantly higher than that of diclofenac group (73%,P<0.05). the clinical indexes of the two groups were significantly improved after treatment (P <0.01). |
| synthesis route | method 1: 2-methoxynaphthalene is used as raw material to prepare nabumetone by bromination, Grignard reaction, addition and reduction. due to the use of cheap reagents, the cost is reduced and the yield is increased by 21.8% compared with the original. the specific reaction process is as follows: method 2: 2-methoxynaphthalene is used as raw material, nabumetone was synthesized under ultrasound and using a novel catalyst. By comparing with the route reported in the literature, the reaction time for synthesizing this drug under the action of ultrasonic wave is shortened from the original 13.5 h to 7.5 h, and the yield is increased from 23.9% to 39.4% h. the specific reaction process is as follows: method 3:β-naphthyl ether reacts with acrylic in the presence of AlCl3 to generate 3-(6-methoxy -2-naphthyl) acrylic, and then reacts with Grignard reagent of CH3Cl, the product is hydrolyzed to obtain caidingmeidone, and the total yield of the two-step reaction is about 45%. The specific reaction process is as follows: |
| Pharmacokinetics | After oral administration, it is absorbed in the duodenum as a non-acidic precursor and converted into the main active product 6-methoxy-2-naphthaleneacetic acid (6-MNA). Tmax is 4~6h. Taking with food or milk can increase the absorption rate and increase the peak plasma concentration of 6-MNA by 1/3. Once daily medication reached a steady state in about 3 to 6 days. The PPB of 6- MNA can reach 99% and Vd is 75 L. 6-MNA is widely distributed in the body, mainly in the liver, lung, heart and intestine, and is easy to spread to synovial tissue, synovial fluid, fibrous capsule tissue and various inflammatory exudates. Can enter milk and placenta. 6- MNA clearance T1/2 is 23 h in young people and 30 h in old people. The steady-state blood drug concentration of 6-MNA was not affected by renal function. Old people achieve higher plasma concentrations than young people, however, once-daily administration does not cause drug accumulation. 6-MNA is converted into inactive products by liver, 80% excreted from urine and 10% excreted from feces. |
| indications | various acute and chronic inflammatory arthritis, soft tissue rheumatism, sports soft tissue injury, sprain and contusion, etc. Others can also be treated such as postoperative pain, post-traumatic pain, toothache, pain after tooth extraction, dysmenorrhea, etc. |
| specification | tablet: 0.25g; 0.5g. Capsule: 0.2g; 0.25g. Dispersed tablets: 0.5g. Dry suspension: 0.5g. |
| usage and dosage | oral administration for adults, 1g, qd each time, before going to bed. Adults weighing less than 50kg can take 0.5g daily as the starting dose and gradually increase to the effective dose. For severe or persistent symptoms, or acute exacerbation, an additional 0.5~1g, early morning administration; children's dosage has not been established; renal insufficiency should be appropriately reduced. |
| adverse reactions | 1. the incidence of adverse reactions is about 15%. Nausea, vomiting, indigestion, diarrhea, abdominal pain, constipation or stool occult blood test positive, dizziness, headache, tinnitus, fatigue, insomnia, nervousness, lethargy, allergic rash and itching, angioedema, jaundice, etc. 2. Occasionally, peptic ulcer, abnormal liver function, hypertension, anemia, coagulation dysfunction, thrombocytopenia, vasculitis, pseudoporphyria may occur. Hematuria and proteinuria are rare, and can even lead to acute renal failure, interstitial nephritis, nephrotic syndrome and renal papillary necrosis, asthma, dyspnea, allergic pneumonia and idiopathic interstitial pneumonia. |
| drug interaction | patients receive oral anticoagulants, hydantoin, anticonvulsants or sulfonylurea hypoglycemic drugs while using this product, which can increase the blood drug concentration of the latter. If you must take it together, adjust the dose. |
| precautions | 1. patients with active peptic ulcer or bleeding, severe liver dysfunction, pregnant women and lactating women, those who are allergic to this product or aspirin and other non-steroidal anti-inflammatory drugs are prohibited. 2. patients with reduced renal function, history of heart failure or edema, hypertension, liver disease, hemophilia, vonWillebrand disease, severe thrombocytopenia (platelet count less than 50000/mm3), patients using anticoagulant drugs, heavy drinkers and children should use it with caution. 3. acute phase reactants (such as erythrocyte sedimentation rate (ESR) or C- reactive protein), blood routine and fecal occult blood test, serum sodium, potassium, blood urea nitrogen, creatinine and alanine aminotransferase should be monitored before and during medication. |
| medication for pregnant and lactating women | nabumetone is not recommended for the last 3 months of pregnancy. |
| main reference | [1] founder et al. improvement of synthesis process of nabumetone. journal of China pharmaceutical university. 2004,35 (1):90~91. [2] Liu et al. comparison of efficacy and safety of nabumetone and nimesulide in the treatment of rheumatoid arthritis. Chinese journal of new drugs and clinic. 2002, 21 (10):588-591. [3] Editor-in-Chief Ren Juanqing. Handbook of Practical Drugs. Jinan: Shandong Science and Technology Press. 2012. No. 759-760 [4] Jiang Jinliang, Zhang Shiling, editor-in-chief Ji Dahong. Handbook of commonly used new drugs. Jinan: Shandong Science and Technology Press. 2000. [5] Zhou Wen, Zhou Xubin, editor-in-chief of Han Wenxiu. The latest drug manual. Jinan: Shandong Science and Technology Press. 2005. [6] Chen xiaoquan et al. improvement of nabumetone synthesis. organic chemistry. 2010,30(7):1069~1071. [7] you tin ba et al. a new method for synthesizing nabumetone. journal of chinese pharmaceutical industry. 1996.27(8):339-340. [8] Xu Jingfeng, editor-in-chief Yang Benming. Manual of Clinical Prescription Drugs. Nanjing: Jiangsu Science and Technology Press. 2009. |
| use | has anti-inflammatory, analgesic and antipyretic effects, and is used for the treatment of rheumatism |
Last Update：2024-04-09 02:00:08
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View History
Raw Materials for nabumetone
Cupric acetate,anhydrous
Nitrogen
Dimethyl sulfate
Calcium chloride
Sodium Chloride
Hydrogen
Ethyl Alcohol
Sodium ethoxide
Acetyl Chloride
Nitrogen
Dimethyl sulfate
Calcium chloride
Sodium Chloride
Hydrogen
Ethyl Alcohol
Sodium ethoxide
Acetyl Chloride