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Naproxen sodium powder, white or off white crystalline powder; Odorless; Slightly hygroscopic. The product is easily soluble in water, slightly soluble in ethanol, slightly soluble in acetone, and almost insoluble in chloroform or toluene. It is a lipophilic, non acidic, inactive naproxen prodrug. Once absorbed, it will be hydrolyzed into pharmacologically active naproxen. Medical products are non steroidal anti-inflammatory drugs. It is suitable for relieving all kinds of mild to moderate pain, such as pain after tooth extraction and other operations, primary dysmenorrhea and headache. It is also applicable to rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, juvenile arthritis, tendonitis, bursitis and acute gouty arthritis. It can alleviate the pain, swelling and restricted activity of arthritis. The products of this laboratory are basic chemicals for scientific research only.
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Chemical Formula |
C14H13NaO3 |
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Exact Mass |
252 |
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Molecular Weight |
252 |
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m/z |
252 (100.0%), 253 (15.1%), 254 (1.1%) |
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Elemental Analysis |
C, 66.66; H, 5.19; Na, 9.11; O, 19.03 |
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Caipusheng was first synthesized by Harrison et al. In the late 1980s, when syntex, the United States, monopolized it. The annual output of syntex pharmaceutical company in the United States was 800 tons. It was first patented and put into industrial production. In 1992, it exceeded US $1billion, becoming another antipyretic and analgesic drug that crossed the US $1billion mark after ibuprofen's patent expired in 1993. In 1994, due to the good curative effect of gongpusheng and the new drug release system that has been coming out in recent years.
The medical drug is a non steroidal anti-inflammatory drug. It is suitable for relieving all kinds of mild to moderate pain, such as pain after tooth extraction and other operations, primary dysmenorrhea and headache. It is also applicable to rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, juvenile arthritis, tendonitis, bursitis and acute gouty arthritis. It can alleviate the pain, swelling and restricted activity of arthritis. Compared with aspirin and indomethacin, the effect of symptom relief is similar, but the incidence and severity of gastrointestinal and nervous system adverse reactions are low.
The medical drug is a non steroidal anti-inflammatory drug. It is suitable for relieving all kinds of mild to moderate pain, such as pain after tooth extraction and other operations, primary dysmenorrhea and headache. It is also applicable to rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, juvenile arthritis, tendonitis, bursitis and acute gouty arthritis. It can alleviate the pain, swelling and restricted activity of arthritis. Compared with aspirin and indomethacin, the effect of symptom relief is similar, but the incidence and severity of gastrointestinal and nervous system adverse reactions are low.
Naproxen sodium powder, as a non steroidal anti-inflammatory drug (NSAID), exerts analgesic, anti-inflammatory, and antipyretic effects by inhibiting prostaglandin synthesis, and is widely used in the treatment of various pain and inflammatory diseases. Its uses cover multiple fields such as arthritis related diseases, soft tissue inflammation, postoperative pain, primary dysmenorrhea, and fever management.
1. Diseases related to arthritis
Rheumatoid arthritis (RA) and osteoarthritis (OA): Naproxen sodium can significantly alleviate joint pain, swelling, and morning stiffness, and improve joint mobility. A double-blind trial showed that its effectiveness in treating RA reached 94%, and long-term use can delay joint structure damage. Its anti-inflammatory effect is about 11 times stronger than that of an equivalent dose of prednisone, and its analgesic and antipyretic effects are 7 times and 22 times stronger than aspirin. It has a stronger selective inhibitory effect on COX-2, so its gastrointestinal adverse reactions are relatively small.
Ankylosing spondylitis (AS): By inhibiting the inflammatory response of the spine, reducing lower back pain and stiffness, and improving the quality of life of patients.
Juvenile arthritis (JIA): Suitable for children with chronic joint inflammation, the dosage should be adjusted according to body weight (usually 10-15mg/kg per day, divided into 2 oral doses).
Acute gouty arthritis: Quickly relieve joint redness, swelling, heat and pain, but combined with colchicine or glucocorticoids to control disease progression.
2. Soft tissue inflammation
Tendinitis and bursitis: By inhibiting the release of local inflammatory mediators, it reduces the pain and swelling of tendons or bursae, and is commonly used in diseases such as shoulder periarthritis and tennis elbow.
Acute post-traumatic pain: such as sprains and contusions, can be used for a short period of time to control inflammatory reactions and promote functional recovery.
3. Pain management
Postoperative pain: As part of a multimodal analgesia regimen, it can reduce the use of opioid drugs and lower the risk of respiratory depression.
Primary dysmenorrhea: By inhibiting the synthesis of prostaglandins in the endometrium, menstrual pain can be relieved with an effective rate of about 70% -80%.
Headache and toothache: It has a rapid analgesic effect on migraine, tension headache, and toothache, but organic lesions need to be ruled out.
4. Heat management
Infectious or non infectious fever: acts on the hypothalamic thermoregulatory center, blocks the influence of pyrogens on the thermoregulatory point, and promotes the recovery of fever patients' body temperature to normal. It is suitable for fever states caused by colds, pneumonia, etc., but requires etiological treatment.
1. Inhibition of prostaglandin synthesis
Naproxen sodium reduces the production of inflammatory mediators such as prostaglandin E2 (PGE2) by non selectively inhibiting cyclooxygenase (COX-1 and COX-2), thereby decreasing the sensitivity of pain nerve endings to pain stimuli and alleviating redness, swelling, and thermal pain caused by vasodilation and exudation. It has a strong selective inhibitory effect on COX-2, so the gastrointestinal adverse reactions are relatively mild.
2. Blocking the release of inflammatory mediators
By inhibiting arachidonic acid metabolism and reducing the release of white blood cell chemokines (such as leukotriene B4), the infiltration and activation of white blood cells into inflammatory sites can be inhibited, thereby reducing tissue damage.
3. Intervention of temperature regulation center
Acting on the hypothalamic thermoregulatory center, promoting heat dissipation process, suitable for low fever management, but seeking medical attention promptly if the body temperature exceeds 39 ℃ or if the fever persists.
There are three synthetic routes for naproxen sodium powder, which are as follows:
1. Synthetic route with 6-methoxy-2-acetylnaphthalene as raw material.
The synthesis route of naproxen sodium from 6-methoxy-2-acetylnaphthalene mainly involves multiple chemical reactions to convert the raw materials into the target product.
Firstly,
6-methoxy-2-acetylnaphthalene is used as the starting material to undergo functional group conversion and rearrangement through specific chemical reactions (such as carbonyl addition) in the presence of a catalyst. This step aims to introduce or adjust key functional groups in the molecular structure, laying the foundation for subsequent reactions.
Subsequently,
through a series of reaction steps such as oxidation, reduction, esterification, etc., the raw material is gradually converted into an intermediate of naproxen. These reaction conditions need to be strictly controlled to ensure high yield and low by-product generation. During this process, chemical reagents such as cyanides, acids, bases, and appropriate solvents may be used to promote the reaction.
Finally,
Under appropriate conditions, the intermediate is converted to naproxen and further combined with sodium ions through salt formation reaction to produce naproxen sodium. This step typically involves pH adjustment of the solution, temperature control, and possible crystallization processes to obtain high-purity and stable naproxen sodium products.
2. Synthetic route using 6-methoxy-2-propionyl tea as raw material.
The synthetic route for producing naproxen sodium from 6-methoxy-2-propionylnaphthalene (note that "tea acid" may be a misspelling of "naphthalene") usually involves a series of chemical conversion steps.
Firstly,
It should be clarified that 6-methoxy-2-propionylnaphthalene is an important intermediate in the synthesis of naproxen.
In the synthetic route, 6-methoxy-2-propionylnaphthalene may undergo rearrangement reactions or similar conversion processes to introduce or adjust functional groups in the molecule, making it closer to the structure of naproxen. This step may involve the use of catalysts, such as Lewis acids, to facilitate the reaction.
Subsequently,
Through a series of reaction steps such as oxidation, reduction, esterification, etc., the intermediate is further converted into naproxen. These reaction conditions need to be strictly controlled to ensure high yield and low by-product generation. During this process, various chemical reagents and solvents may be used to optimize the reaction conditions.
Finally,
Naproxen is combined with sodium ions to generate naproxen sodium. This step typically involves pH adjustment of the solution, temperature control, and possible crystallization processes to obtain high-purity and stable naproxen sodium products.
3. Synthetic route with 2-methoxynaphthalene as raw material
The synthesis route of naproxen sodium powder from 2-methoxynaphthalene usually involves multiple chemical transformations, aiming to gradually construct the core structure of naproxen and ultimately introduce the sodium salt.
Firstly,
2-methoxynaphthalene as the starting material requires a specific chemical reaction, such as Friedel Crafts acylation, to introduce an acyl group (such as acetyl or propionyl) to form the corresponding ketone intermediate. This step is a crucial step in constructing the key carbonyl moiety in naproxen molecules.
Subsequently,
The ketone intermediate needs to undergo a series of complex transformations, including possible oxidation, reduction, rearrangement, and other reactions, to adjust the molecular structure and introduce other necessary functional groups. These reaction conditions need to be precisely controlled to ensure the purity and yield of the product.
Next,
In the stage approaching the target product naproxen, esterification reaction is usually carried out to introduce carboxylic acid groups into the molecule, forming the precursor of naproxen. This step is one of the key steps in synthesizing naproxen, as it directly determines the structure and properties of the final product.
Finally,
The precursor of naproxen is combined with sodium ions to prepare naproxen sodium through a salt formation reaction. This step typically involves pH adjustment of the solution, temperature control, and possible crystallization processes to obtain high-purity and well stable naproxen sodium products.
4. Asymmetric synthesis
Asymmetric synthesis methods typically start from starting materials with chiral centers, such as chiral alcohols, chiral acids, or chiral catalysts. In the synthesis of naproxen sodium, chiral reagents such as (2R, 3R) - dimethyl tartrate may be chosen as starting materials or auxiliary reagents. The key steps include asymmetric induction reactions, such as asymmetric cyanide, asymmetric hydrocyanide, asymmetric catalytic hydrogenation, etc. These reactions can selectively generate intermediates or products with specific configurations under mild conditions. This method is an efficient and direct method for preparing optically pure naproxen sodium. Asymmetric synthesis method has the advantages of short route, low cost, and high optical purity of the product, and is an important means for preparing optically pure drugs.
Overview of synthetic routes
Asymmetric induction reaction:
Firstly, through asymmetric induction reactions, such as asymmetric cyanide or hydrogen cyanide reactions catalyzed by chiral catalysts, the starting material is converted into intermediates containing chiral centers.
Conversion of intermediates:
Subsequently, a series of conversion reactions are carried out on the intermediates, such as hydrolysis, rearrangement, esterification, etc., to construct the core structure of naproxen. These reactions need to be carried out under strictly controlled conditions to ensure the retention of chiral centers and the purity of the products.
Salt formation reaction:
Finally, the obtained naproxen precursor is combined with sodium ions to prepare naproxen sodium through salt formation reaction. This step typically involves pH adjustment of the solution, temperature control, and possible crystallization processes.
The equivalent dosage of naproxen sodium powder is 1:1.1. After oral administration, they are easily and completely absorbed from the gastrointestinal tract, but the absorption rate of sodium salt is faster. It takes 1 hour to reach the peak concentration of blood drug, and it takes 2 hours for free acid. Gastric contents can prolong its absorption time, but do not affect its absorption rate. The binding rate of plasma protein was high (>99.5%). It can be distributed in the whole body, reach the effective concentration in synovial fluid, and enter the fetus through the placenta. It is metabolized by the liver and excreted by the kidney. Most of the excretion is metabolites, with a small amount of prototype. About 3% is excreted from feces and 1% is secreted by milk. Plasma t1/2 was 13 hours. It can also be administered rectally, but the absorption rate is slower than oral administration.
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