Naproxen etemesil

• CAT Number: I008238
• CAS Number: 385800-16-8
• Molecular Formula: C17H20O5S
• Molecular Weight: 336.40
• Purity: ≥95%
• Synonyms: 2-methylsulfonylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• InChI: InChI=1S/C17H20O5S/c1-12(17(18)22-8-9-23(3,19)20)13-4-5-15-11-16(21-2)7-6-14(15)10-13/h4-7,10-12H,8-9H2,1-3H3/t12-/m0/s1
• InChIKey: JGBUBSOKFSVXKS-LBPRGKRZSA-N
• SMILES: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCS(=O)(=O)C

Naproxen etemesil is a lipophilic, non-acidic, inactive proagent of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a COX-1 and COX-2 inhibitor with IC50s of 8.72 and 5.15 μM, respectively in cell assay.
Naproxen etemesil is a lipophilic, non-acidic, inactive prodrug of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a well known nonsteroidal anti-inflammatory drug. Naproxen is approximately equipotent inhibitor of COX-1 and COX-2 in intact cells with IC50s of 2.2 μg/mL and 1.3 μg/mL, respectively[1].
Naproxen exerts an anti-inflammatory and antifibrotic effect in mouse model of bleomycin-induced lung fibrosis. Naproxen also downregulates TGF-β levels and Smad3/4 complex formation[2]. Naproxen is shown to inhibit the time-courses of pain, fever and PGE2 with similar potencies (IC50=27, 40, 13 μM)[3].

Reference

[1]. Mitchell JA, et al. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11693-7.
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[2]. Rosa AC, et al. Prevention of bleomycin-induced lung inflammation and fibrosis in mice by naproxen and JNJ7777120 treatment. J Pharmacol Exp Ther. 2014 Nov;351(2):308-16.
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[3]. Krekels EH, et al. Pharmacokinetic-pharmacodynamic modeling of the inhibitory effects of naproxen on the time-courses of inflammatory pain, fever, and the ex vivo synthesis of TXB2 and PGE2 in rats.
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