naproxen   

GtoPdb Ligand ID: 5230

Synonyms: (S)-naproxen | Aleve® | Naprosy®
naproxen is an approved drug (FDA (1976))
Compound class: Synthetic organic
Comment: Naproxen is one of the 2-arylpropionic acid ('profen') family of nonsteroidal anti-inflammatory drugs (NSAIDs), like ibuprofen.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 46.53
Molecular weight 230.09
XLogP 2.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc2c(c1)ccc(c2)C(C(=O)O)C
Isomeric SMILES COc1ccc2c(c1)ccc(c2)[C@@H](C(=O)O)C
InChI InChI=1S/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)/t9-/m0/s1
InChI Key CMWTZPSULFXXJA-VIFPVBQESA-N
No information available.
Summary of Clinical Use
Used in the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and acute gout. Also used in pain relief in the treatment of primary dysmenorrhea.
Mechanism Of Action and Pharmacodynamic Effects
Naproxen inhibits cyclooxygenase enzymes COX-1 and COX-2 leading to a reduction in inflammation.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02052908 Naproxen in Preventing DNA Mismatch Repair Deficient Colorectal Cancer in Patients With Lynch Syndrome Phase 1 Interventional National Cancer Institute (NCI) Naproxen demonstrates chemopreventive activity in patients with Lynch syndrome (LS), potentially via a mechanism that modulates the immune activation that is observed in LS colorectal adenomas and tumours. 2
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