S-Lenalidomide - CAS 202271-91-8

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    • Specification
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        IUPAC Name
        (S)-3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione; S-(-)-Lenalidomide
    • Properties
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    • Reference Reading
      • 1. Lenalidomide, a blockbuster drug for the treatment of multiple myeloma: Semipreparative separation through supercritical fluid chromatography and vibrational circular dichroism spectroscopy
        Yilun Yan, Jun Fan, Dong Guo, Yuemei Lin, Yecai Lai, Tai Wang, Hao Gao, Xinsheng Yao, Weiguang Zhang J Sep Sci. 2018 Oct;41(20):3840-3847.doi: 10.1002/jssc.201800519.Epub 2018 Sep 12.
        Semipreparative separation of lenalidomide has been performed through supercritical fluid chromatography. In regard to retention and resolution of lenalidomide, effects of chromatographic conditions, such as chiral stationary phases, organic co-solvents, mobile phases, and column temperature, have been studied in detail. Amylose tris(3, 5-dimethylphenylcarbamate)-coated and the single-urea-bound β-cyclodextrin chiral stationary phases exhibited good separation performances for lenalidomide in the CO2 /methanol mixture. Then, a comparative study of semipreparative separation of lenalidomide has been carried out on these two chiral stationary phases. As indicated, separation of lenalidomide on the β-cyclodextrin-bound column was much better than the other. Under the optimized conditions, the loading per injection was 30 mg, the cycle time was 5 min, and the recoveries of two enantiomers were about 81.7 and 79.5%, respectively. Moreover, the vibrational circular dichroism spectrum of the first-eluted enantiomer in d6 -dimethylsulfoxide solution was consistent with the calculated pattern based on the S configuration, revealing that it should be (S)-(-)-lenalidomide. Briefly, this separation method through supercritical fluid chromatography might provide favorable information for rapid separation, enantioselective assessment, and absolute configurations of chiral pharmaceuticals.
        2. Single-dose pharmacokinetics of lenalidomide in healthy volunteers: dose proportionality, food effect, and racial sensitivity
        N Chen, C Kasserra, J Reyes, L Liu, H Lau Clinical TrialCancer Chemother Pharmacol. 2012 Nov;70(5):717-25.doi: 10.1007/s00280-012-1966-z.Epub 2012 Sep 6.
        Purpose:Lenalidomide is an immunomodulatory drug with efficacy in various hematological malignancies. The purpose of these studies was to evaluate the single-dose pharmacokinetics of lenalidomide, including dose proportionality, food effect, and racial sensitivity. Methods:Three studies were conducted including a total of 58 healthy subjects: a randomized, single-blind, alternating group, single-ascending dose study; a randomized, two-way crossover food effect study; and a randomized, double-blind, two-group, within-subject, single-ascending dose study. Results:Oral absorption of lenalidomide was rapid and the maximum plasma concentration (C (max)) was observed approximately 1 h post-dose. Co-administration with a high-fat meal reduced the area under the concentration-time curve (AUC) and C (max) by approximately 20 and 50 %, respectively, and delayed time to C (max) (t (max)) by 1.63 h. However, phase III trials were dosed without regard to food; therefore, clinical relevance of the food effect was minimal. The terminal elimination half-life (t (½)) was 3-4 h at doses up to 50 mg and was not affected by food. The AUC and C (max) were proportional to lenalidomide single doses (5-400 mg), and total and renal clearance were dose-independent. The R- to S-lenalidomide ratio in plasma was stable over time, approximately 45-55 % of total drug. There were no differences in pharmacokinetic parameters, dose-exposure relationship, or enantiomeric ratio, between Japanese and Caucasian subjects.Conclusion:Lenalidomide displayed linear pharmacokinetics from doses 5-400 mg in healthy subjects. Although food reduced bioavailability, this was not considered clinically relevant. Lenalidomide was generally well tolerated in both ethnic groups.
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