5436. Lenalidomide

Nomenclature

CAS number: 191732-72-6
3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione; 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline; CC-5013; Revimid (Celgene); Revlimid (Celgene).
C13H13N3O3; mol wt 259.26.
C 60.22%, H 5.05%, N 16.21%, O 18.51%.

Description and references

Immunomodulatory drug; analog of thalidomide, q.v. Prepn: G. W. Muller et al., US 5635517 (1997 to Celgene); and in vitro TNF-α inhibition: eidem, Bioorg. Med. Chem. Lett. 9, 1625 (1999). LC-MS determn in plasma: T. M. Tohnya et al., J. Chromatogr. B 811, 135 (2004). Clinical evaluation in multiple myeloma: P. G. Richardson et al., Blood 100, 3063 (2002); in myelodysplastic syndromes: A. List et al., N. Engl. J. Med. 352, 549 (2005). Review of development, pharmacology and therapeutic potential: C. S. Mitsiades, N. Mitsiades, Curr. Opin. Investig. Drugs 5, 635-647 (2004); of clinical experience in multiple myeloma: T. Hideshima et al., Expert Opin. Invest. Drugs 15, 171-179 (2006).

Chemical structure

Properties

Off-white to pale-yellow solid powder. Sol in organic solvent/water mixtures and buffered aqueous solvents. More sol in organic solvents and low pH solutions. Soly significantly lower in less acidic buffers (≈0.4-0.5 mg/ml). Racemic mixture of S() and R(+) with a net optical rotation of zero.

Therapeutic Category

Immunomodulator.

Keywords

Immunomodulator