Naproxene
Naproxene
CAS: 22204-53-1
Molecular Formula: C14H14O3
Naproxene - Names and Identifiers
| Name | Naproxene |
| Synonyms | Naproxen Naproxene ()-propionicaci (+)-2-naphthaleneaceticaci ()-2-(methoxy-2-naphthyl)-propionicacid ()-2-(methoxy-2-naphthyl)-propionsaeure (+)-2-(Methoxy-2-naphthyl)-propionsaeure (+)-2-(methoxy-2-naphthyl)-propionicacid (+)-2-(Methoxy-2-naphthyl)-propionic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoate (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (+)-6-Methoxy-alpha-methyl-2-napthaleneacetic acid (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid |
| CAS | 22204-53-1 |
| EINECS | 244-838-7 |
| InChI | InChI=1/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/p-1/t9-/m0/s1 |
Naproxene - Physico-chemical Properties
| Molecular Formula | C14H14O3 |
| Molar Mass | 230.26 |
| Density | 1.1450 (rough estimate) |
| Melting Point | 152-154 °C (lit.) |
| Boling Point | 332.25°C (rough estimate) |
| Specific Rotation(α) | D +66° (in chloroform) |
| Flash Point | 9℃ |
| Water Solubility | Insoluble in water. |
| Solubility | Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol. |
| Vapor Presure | 3.01E-07mmHg at 25°C |
| Appearance | White to yellow crystalline powder |
| Color | White to Almost white |
| Merck | 14,6417 |
| BRN | 3591067 |
| pKa | pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain) |
| Storage Condition | 2-8°C |
| Refractive Index | 67.5 ° (C=1, CHCl3) |
| MDL | MFCD00010500 |
| Physical and Chemical Properties | Melting point 153-154°C |
| Use | Used as an anti-inflammatory analgesic |
Naproxene - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R36/37/38 - Irritating to eyes, respiratory system and 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.) S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UF5275000 |
| HS Code | 29189900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski) |
Naproxene - Upstream Downstream Industry
| Raw Materials | 2-Naphthol Toluene Methyl alcohol Hydrogen |
Naproxene - Reference
| Reference Show more | 1. Wang Huicheng, Liu Xiaofeng, Yang Ninglian, et al. Determination of Blood Concentration of Irbesartan Tablets in Rats and Pharmacokinetic Study [J]. Chinese Pharmacy 2010(29):2712-2714. 2. Song Yanbo, Zhao Guishan, Ru Xiaofei, Hou Kelin, Mengzhou, Li Xinjie, Meng Qingrong, Wang Handong. Preparation of Indomethacin Artificial Antigen and Its Polyclonal Antibody [J]. Animal husbandry and veterinary 2019 51(10):44-48. 3. [IF = 7.514] Nan Zhang et al."Hydrophilic carboxyl supported immobilization of UiO-66 for novel bar sorptive extraction of non-steroidal anti-inflammatory drugs in food samples." Food Chem. 2021 Sep;355:129623 4. [IF = 4.759] Yan Gao et al."Novel solid-phase extraction filter based on a zirconium meta-organic framework for determination of non-steroidal anti-inflammatory drugs residues." J Chromatogr A.2021 Aug;1652:462349 5. [IF = 7.312] Yunyun Li et al."Mass transfer enhancement for rapid, selective extraction of pharmaceuticals by enlarging the microporous on isostructural zeolitic imidazolate Framework-8." SEPARATION AND PURIFICATION TECHNOLOGY. 2022 Jul;293:121102 |
Naproxene - Reference Information
| LogP | 3.18 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| adverse reactions | [adverse reactions] 1. digestive tract reactions: the side effects of this product are less and lighter than other non-steroidal anti-inflammatory drugs. There are a few cases of anorexia, nausea, vomiting, diarrhea and other stomach discomfort. In severe cases, gastrointestinal bleeding, liver function damage and jaundice are occasionally seen. 2. Central nervous response: manifested as depression, lethargy, headache, dizziness, sweating, fatigue, hearing loss and visual impairment. 3. Allergic reaction: This product is cross-allergic with aspirin, and skin itching, allergic rash, urticaria, shortness of breath, dyspnea, etc. may occur. Therefore, it should be used with caution for aspirin allergy and the elderly, and pregnant women should not be used. 4. Other reactions: very few patients have granulocytopenia, thrombocytopenic purpura, aplastic anemia, etc. Occasionally kidney damage, such as proteinuria, hematuria, nephrotic syndrome, interstitial nephritis and reversible renal failure in the kidney. Therefore, patients with coagulation mechanism disorders, thrombocytopenia, asthma, renal insufficiency and peptic ulcer should be used with caution. |
| Application | Naproxen is a non-steroidal anti-inflammatory drug, a PG synthase inhibitor, which can inhibit prostate synthase and has significant analgesic and antipyretic effects, Oral absorption is completely rapid, the plasma concentration reaches a peak value 2 to 4 hours after one administration, and it binds to plasma proteins in the blood above 99%, t1/2 is 13~14 hours, and about 95% is excreted from urine as prototype and metabolites. Clinically used for the treatment of rheumatism and rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, gout, arthritis, tenosynovitis. It can also be used to relieve pain caused by musculoskeletal sprains, contusions, injuries and dysmenorrhea. However, it should be noted that, like other non-steroidal anti-inflammatory drugs, severe gastrointestinal adverse reactions may occur at any time during naproxen treatment. Therefore, patients with active gastric duodenal ulcers should not be used. Patients with gastrointestinal diseases should be taken under strict medical supervision. |
| Preparation | A method for recovering D,L-naproxen methyl ester material to prepare D,L-naproxen, the preparation method includes the following steps: 1) Distillation: using propionyl naphthyl methyl ether as the starting material, through bromination, ketal, rearrangement, hydrolysis, decolorization, acidification, centrifugation to prepare D,L-naproxen crude, then add 75% methanol to the crude D and L-naproxen, heat up and dissolve, cool down, crystallize, and filter by suction. The filter cake obtained by suction filtration is D,L-naproxen fine, and the filtrate obtained by suction filtration is methanol mother liquor; Distill the methanol mother liquor, evaporate most of the methanol until it is evaporated to dry, and the obtained solid base material is used as a distillation product for standby. The main components in the distillation product are D,L-naproxen and D,L-naproxen methyl ester; 2) Extraction: Step (1) The distilled product obtained is dissolved in toluene, stirred for extraction, stratified, discarded water layer, and took toluene layer for later use; 3) Methylation: Step (2) Add methanol and concentrated sulfuric acid to the toluene layer, stir, heat and reflux to obtain D,L-naproxen methyl ester crude; 4) Distillation and purification: the crude D,L-naproxen methyl ester obtained in step (3) is first steamed out of toluene under normal pressure, then the former fraction is steamed out under reduced pressure, and finally DL-naproxen methyl ester is steamed out under reduced pressure; 5) hydrolysis: water and sodium hydroxide solution are added to the D,L-naproxen methyl ester obtained in step (4), heated, stirred and refluxed, and the hydrolysate is D,L-naproxen sodium. 6) Acidification: Under heating conditions, D,L-naproxen sodium obtained in step (5) is adjusted to pH 1~2 with hydrochloric acid, suction filtration, washing the filter cake with water until the filtrate is neutral, and drying to obtain D,L-naproxen. |
| use | naproxen is a non-steroidal anti-inflammatory analgesic, used to relieve fever and inflammation and pain related to arthritis or other symptoms, with anti-inflammatory, antipyretic and analgesic effects. Naproxen works by inhibiting cyclooxygenase, an enzyme involved in the production of prostaglandins, an inflammatory mediator. Naproxen also has the following uses: 1. Naproxen can improve the body's resistance. For this reason, it can supplement the kidney qi deficiency caused by the body's weakness, and the related symptoms caused by the drowsiness of the gastrointestinal motility system are all huge. effect. 2. Naproxen has a good inhibitory effect on Helicobacter pylori. Can be very good treatment of atrophic gastritis, superficial gastritis, duodenal ulcer problems. In addition, it can also promote the metabolism of gastric acid after improving the effect of gastrointestinal motility system. Assist the body's digestion and absorption and digestion. 3. Naproxen also has very good treatment for rheumatism and rheumatoid symptoms. Many people suffering from long-term rheumatic diseases obviously feel that rheumatism has been relieved very well after taking naproxen. Therefore, naproxen is used for long-term control and is not allowed to produce it again. 4. Clinical experiments have found that naproxen can reasonably improve pancreatic activity. The actual effect is to reduce the level of blood sugar volume, and then repair the volume of blood sugar to all normal levels. |
| Production method | 2-naphthol is methylated and acetylated to obtain 6-methoxy-2-naphthenone, and then condensed with chloroacetate, and then obtained by isomerization, hydrolysis, oxidation, neutralization, and resolution. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral administration-rat LD50 248 mg/kg; Oral administration-mouse LD50: 360 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic and spicy smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | water, dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:07
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Raw Materials for Naproxene