(S)-(+)-Ibuprofen

(+)-Ibuprofen (CAS No. 51146-56-6) is a highly effective non-steroidal anti-inflammatory drug (NSAID) whose core biological activities are anti-inflammatory, analgesic, and antipyretic. Its primary targets are cyclooxygenase-1/2 (COX-1/COX-2). It blocks prostaglandin synthesis by competitively inhibiting COX activity, with slightly higher selectivity for COX-2 than COX-1. In vitro, it inhibits human recombinant COX-1 with an IC?? of about 2.5 μM and COX-2 with an IC?? of about 1.9 μM. It shows growth inhibition against the aquatic alga Chlorella pyrenoidosa with an EC?? of 0.1–0.3 mg/L, and reproduction inhibition against Daphnia magna with an EC?? of 1–100 μg/L. Common application concentrations: for in vitro cell experiments (anti-inflammatory / enzyme activity assays), 1–100 μM; for animal experiments (mouse / rat anti-inflammatory models), oral / intraperitoneal doses of 5–200 mg/kg; for environmental toxicology experiments, exposure concentrations for aquatic organisms of 0.1 μg/L–100 mg/L. Clinically effective therapeutic concentrations correspond to oral doses of: adults 200–400 mg per dose, 3 times per day (total 600–1200 mg/day), with peak plasma concentrations reaching 20–50 μg/mL (100–250 μM); for children, 5–10 mg/kg/day divided into 3 doses, with effective anti-inflammatory and analgesic plasma concentrations of 10–20 μg/mL. It shows good tolerability, no obvious mitochondrial toxicity, stronger activity, and fewer side effects than the R-enantiomer.

References:

[1] Ha MW, Paek SM. Recent Advances in the Synthesis of Ibuprofen and Naproxen. Molecules. 2021 Aug 7;26(16):4792. doi: 10.3390/molecules26164792. PMID: 34443379; PMCID: PMC8399189.

[2] Jan-Roblero J, Cruz-Maya JA. Ibuprofen: Toxicology and Biodegradation of an Emerging Contaminant. Molecules. 2023 Feb 23;28(5):2097. doi: 10.3390/molecules28052097. PMID: 36903343; PMCID: PMC10004696.