202409-33-4
Etoricoxib
CAS: 202409-33-4
Molecular Formula: C18H15ClN2O2S
202409-33-4 - Names and Identifiers
| Name | Etoricoxib |
| Synonyms | Cis-Anetho Etoricoxib Etoricoxib (MK-663 Etoricoxib Tablets Etoricoxib (200 mg) Etoricoxib impurity A Etoricoxib Solution, 100ppm 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine 5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine Etoricoxib(5-chloro-6'-Methyl-3-(4-(Methylsulfonyl)phenyl)-2,3'-bipyridine |
| CAS | 202409-33-4 |
| EINECS | 682-421-5 |
| InChI | InChI=1/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3 |
| InChIKey | MNJVRJDLRVPLFE-UHFFFAOYSA-N |
202409-33-4 - Physico-chemical Properties
| Molecular Formula | C18H15ClN2O2S |
| Molar Mass | 358.84 |
| Density | 1.298±0.06 g/cm3(Predicted) |
| Melting Point | 134-135°C |
| Boling Point | 510.0±50.0 °C(Predicted) |
| Flash Point | 262.2°C |
| Solubility | Soluble in DMSO, and methanol |
| Vapor Presure | 5.17E-10mmHg at 25°C |
| Appearance | grayish white powder |
| BRN | 8073797 |
| pKa | 4.5(at 25℃) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.6 |
| MDL | MFCD06797512 |
| Use | A specific inhibitor of COX-2. |
202409-33-4 - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R22 - Harmful if swallowed R24 - Toxic in contact with skin |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2811 6.1 / PGII |
| WGK Germany | 3 |
202409-33-4 - Nature
Open Data Verified Data
colorless solid. The melting point was 127-128 °c.
Last Update：2024-01-02 23:10:35
202409-33-4 - Preparation Method
Open Data Verified Data
magnesium and 4-methylthiobenzyl chloride were dissolved in tetrahydrofuran and reacted, and the reaction solution was added to Weinreb amide and toluene for reaction. An aqueous solution of acetic acid was added, followed by additional water and toluene. The layers were separated and the aqueous layer was extracted with toluene. The toluene layers were combined and extracted with dilute hydrochloric acid. Ethyl acetate was added to the extract, and the pH of the aqueous layer was adjusted with aqueous ammonia. The layers were separated and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layers were combined and concentrated to give a pale yellow solid. The solid, sulfuric acid, was dissolved in methanol, heated, and an aqueous solution of sodium tungstate was added, followed by reaction with hydrogen peroxide. Water was added and cooled to room temperature and filtered. The solid was washed with water and dried under vacuum to obtain a ketosulfone compound. The ketosulfone compound, n-propionic acid and 3-amino -2-chloroacrolein, methanesulfonic acid and propionic acid were dissolved in toluene, refluxed and azeotropically dehydrated. After cooling, isopropyl acetate was added, water was added and the aqueous layer was neutralized with concentrated aqueous ammonia. The separated organic layer was washed with a mixed solution of brine and water. The aqueous layers were combined and washed with isopropyl acetate. The organic layers were combined, treated with Darco G-60, concentrated, and recrystallized from isopropyl acetate-hexane to obtain etacoxib.
Last Update：2022-01-01 09:09:33
202409-33-4 - Introduction
Etoricoxib(MK-0663) can selectively inhibit COX-2,IC50 is 1.1_mu_M(LPS-induced prostaglandin E2 synthesis experiment), while IC50 for COX-1 is 116_mu_M (post-coagulation serum thromboxane B2 production experiment).
Last Update：2022-10-16 17:14:48
202409-33-4 - Use
Open Data Verified Data
developed by Merck and approved for marketing in the UK in March 2002. It is a second-generation cyclooxygenase-2 (COX-2) inhibitor. For osteoarthritis and rheumatoid arthritis symptom relief, dental surgery-related acute pain relief and primary dysmenorrhea treatment.
Last Update：2022-01-01 09:09:34
202409-33-4 - Reference Information
| Cyclooxygenase -2(COX-2) inhibitor | Etocoxib (etoricoxib) is a highly selective cyclooxygenase -2(COX-2) inhibitor developed by Merck Company, with its chemical name: 5-chloro-6'-methyl-3-4-(methanesulfonyl) phenyl]-2,3 '-bipyridine. Etoricoxib has a unique chemical structure, namely methanesulfonyl. The introduction of this group not only increases the selectivity of the drug to COX-2, but also does not produce cross-allergic reactions with sulfonamides. Etokoxib was first approved for listing in the UK in 2002, and the subsequent countries and regions include the European Union, Asia Pacific, Australia and Latin America. As of the end of 2013, it has been approved for listing in 97 countries around the world and is widely used in osteoarthritis (osteoarthritis,OA), rheumatoid arthritis, ankylosing spondylitis, chronic low back pain, acute gouty arthritis, primary dysmenorrhea and postoperative pain. Etocoxib has also been listed in Taiwan and Hong Kong. It was listed in mainland China in 2008. The approved indications are acute gouty arthritis and OA. The indications for primary dysmenorrhea were approved in the second half of 2014. As a COX-2 inhibitor, etoricoxib can reduce the risk of gastrointestinal peptic ulcer, perforation and bleeding compared with traditional non-steroidal anti-inflammatory drugs (NSAIDS), and has no sulfonamide group, which has higher safety for patients with sulfonamide allergy, "Chinese Osteoarthritis Diagnosis and Treatment Guidelines (2007 Edition)", "American College of Rheumatology Gout Diagnosis and Treatment Guidelines (2012 Edition)", "Chinese Gout Diagnosis and Treatment Guidelines are recommended (2016 Edition)" are recommended. Xiangyun edited and organized. |
| pharmacological effects | etocoxib is a non-steroidal anti-inflammatory drug, which has anti-inflammatory, analgesic and antipyretic effects in animal models. Within the clinical dose range or higher doses, it is a selective cyclooxygenase-2 inhibitor with oral activity. At present, two subtypes of cyclooxygenase have been confirmed: cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2). COX-1 participates in normal physiological functions mediated by prostaglandins, such as gastric mucosal cell protection and platelet aggregation. Non-selective non-steroidal anti-inflammatory drugs inhibit the production of COX-1, thus causing gastric mucosal damage and reduced platelet aggregation. COX-2 is mainly involved in the production of prostaglandins, which can cause pain, inflammation and fever. Etoricoxib is a selective inhibitor of cyclooxygenase-2, which can reduce these symptoms and signs, reduce gastrointestinal side effects and do not affect platelet function. |
| pharmacokinetics | absorption: oral absorption is good. The average oral bioavailability is close to 100%. When adults take 120mg once a day on an empty stomach until steady state is reached, the peak plasma concentration appears about 1 hour after administration. The pharmacokinetics of this product is linear in the clinical dose range. Distribution: 92% binds to human plasma proteins in the concentration range of 0.05-5mcg/ml. In the human body, the volume of distribution at steady state is about 120 liters. It can pass through the placenta of rats and rabbits, as well as the blood-brain barrier of rats. Metabolism: metabolism is complete, and the content of primary drugs in urine is less than 1%. The main metabolic pathway is catalyzed by cytochrome P450(CYP) enzyme to form 6-carboxylic acid derivatives. Clearance: In healthy individuals, radiation-labeled etoricoxib is given intravenously. The radioactivity of 70% can be detected in urine, and the radioactivity of 20% can be detected in feces. Most of them exist in the form of metabolites, and only less than 2% The drug is excreted in its original shape. |
| drug interaction | warfarin: for stable patients treated with warfarin for a long time, the international normalized ratio (INR) of 120mg prothrombin time per day increased by about 13%. Rifampicin: Rifampicin is a strong inducer of liver metabolism. The combination of this product can reduce the area under the plasma curve (AUC) of this product by 65%. When this product is combined with rifampicin, its interaction should be considered. methotrexate: when the dosage of this product is more than 90mg/day and combined with methotrexate, the toxic reaction related to methotrexate should be considered. Diuretics, angiotensin converting enzyme (ACE) inhibitors and angiotensin II antagonists (AIIAs): Non-steroidal anti-inflammatory drugs including cyclooxygenase-2 selective inhibitors can reduce the antihypertensive effects of diuretics, angiotensin converting enzyme inhibitors and angiotensin II antagonists. Lithium salt: Non-selective non-steroidal anti-inflammatory drugs and selective inhibitors of cyclooxygenase-2 can increase the plasma level of lithium salt. Aspirin: This product can be used simultaneously with low-dose aspirin to prevent cardiovascular events. However, when combined with low-dose aspirin, the incidence of gastrointestinal ulcers or other complications is increased compared with this product alone. Oral contraceptives: When choosing a suitable oral contraceptives and this product to take at the same time, the increase in EE concentration should be considered. Elevated EE concentrations increase the incidence of oral contraceptive-related adverse events (such as the risk of venous thromboembolism in women). others: antacids and ketoconazole (CYP3A4 strong inhibitor) have no clinically significant effect on the pharmacokinetics of this product. |
| indications | 1. treatment of OA: this product has the same curative effect as celecoxib and ibuprofen, and is similar to that of high-dose diclofenac and naproxen. 2. acute gouty arthritis: this product 120mg/d can quickly and effectively relieve pain. it is equally effective compared with indomethacin, the gold standard drug for gouty arthritis, and etoricoxib has better tolerance. the incidence of drug-related adverse events is lower than that of indomethacin. 3. ankylosing spondylitis: etoricoxib and naproxen have similar effects twice a day, and etoricoxib has more significant effects in improving secondary endpoints such as night pain, inflammation, function and flexibility. 4. Rheumatoid arthritis: The results of large-scale and controlled clinical trials show that etoricoxib once a day is more effective than naproxen twice a day, and the patients are well tolerated. 5. Osteoarthritis: This product is as effective as celecoxib 1 time/day and ibuprofen 3 times/day; and its 1 time/day is similar to high-dose diclofenac (3 times/day) and naproxen (3 times/day). 6. Dental postoperative pain: Compared with acetaminophen/codeine and oxycodone/acetaminophen, taking etoricoxib once a day patients get better pain relief. 7. Chronic low back pain: Compare the efficacy of this product and comfort medicine in the treatment of chronic low back pain for 12 weeks. As a result, the clinical efficacy of this product is significantly better than that of comfort medicine. The effect is obvious after 4 weeks, and the lasting effect is more than 3 months. 8. Control of pain in the late stage after thyroid surgery: patients with thyroid surgery were given etoricoxib 1 h before surgery, and patients with acetaminophen oxycodone 6~12 h after surgery were less. |
| safety | compared with diclofenac, there was no significant difference in the incidence of thrombotic cardiovascular events, while the cumulative incidence of gastrointestinal perforation, ulcer and hemorrhage in etocoxib group was significantly lower than that in diclofenac group. The incidence of gastrointestinal adverse events is 50% lower than that of diclofenac sodium. Adverse reactions such as gastrointestinal symptoms (nausea, vomiting, abdominal pain or abdominal discomfort, diarrhea), chest tightness and ankle joint edema occurred during medication. Etoricoxib has a low gastrointestinal response, similar to other selective COX-2 inhibitors, is contraindicated in patients with ischemic heart disease and stroke, and is used with caution in patients with heart disease risk factors. |
Last Update：2024-04-09 20:52:54
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