(S)-naproxen

What is (S)-naproxen

**(S)-Naproxen** is a nonsteroidal anti-inflammatory drug (NSAID) and the active enantiomer of naproxen, known for its potent anti-inflammatory, analgesic, and antipyretic properties. As a selective cyclooxygenase-2 (COX-2) inhibitor, it effectively reduces pain and inflammation with a lower risk of gastrointestinal side effects compared to racemic naproxen. (S)-Naproxen is widely used to treat conditions such as arthritis, menstrual pain, and musculoskeletal disorders. Its chiral purity enhances therapeutic efficacy, requiring lower doses for the same effect. Available in oral and topical formulations, it offers a well-tolerated profile for chronic pain management. This makes (S)-naproxen a preferred choice in clinical practice for targeted NSAID therapy.

Preparation Process: To prepare (S)-naproxen, start with 2-methoxy-6-bromonaphthalene. Perform a Grignard reaction with magnesium in THF, followed by carboxylation with CO₂ to form 2-methoxy-6-naphthoic acid. Reduce the acid to the alcohol using LiAlH₄, then convert it to the tosylate with p-toluenesulfonyl chloride. Perform an SN2 reaction with sodium cyanide to introduce the nitrile group, which is hydrolyzed to the carboxylic acid. Resolve the racemic mixture using a chiral resolving agent like cinchonidine to isolate the (S)-enantiomer. Alternatively, asymmetric synthesis can be employed using chiral auxiliaries or catalysts to directly obtain (S)-naproxen. Purify by recrystallization.

Usage Scenarios: (S)-Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) primarily used to relieve pain, inflammation, and stiffness caused by conditions such as arthritis, gout, menstrual cramps, tendinitis, and bursitis. As the active enantiomer of naproxen, it selectively inhibits cyclooxygenase-2 (COX-2), reducing prostaglandin synthesis and providing analgesic and anti-inflammatory effects with potentially fewer gastrointestinal side effects compared to racemic naproxen. It is commonly prescribed for chronic pain management in osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis. Additionally, (S)-naproxen is used for acute pain relief, including headaches, muscle aches, and dental pain. Its long half-life allows for twice-daily dosing, improving patient compliance.

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