Apremilast-d5

• CAT Number: R022294
• CAS Number: 1258597-47-5
• Molecular Formula: C22H24N2O7S
• Molecular Weight: 465.532
• Purity: ≥95%
• Synonyms: (S)-2-[1-(3-Ethoxy-d5-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione; (S)-N-(2-(1-(3-Ethoxy-d5-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide; Apremilast-d5; CC 10004-d5
• Storage: 2°C to 8°C
• IUPAC Name: N-[2-[(1S)-1-[4-methoxy-3-(1,1,2,2,2-pentadeuterioethoxy)phenyl]-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
• InChI: InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1/i1D3,5D2
• InChIKey: IMOZEMNVLZVGJZ-JVFKXMKASA-N
• SMILES: CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N2C(=O)C3=C(C2=O)C(=CC=C3)NC(=O)C)OC

Apremilast-d5 is intended for use as an internal standard for the quantification of apremilast (Item No. 18502) by GC- or LC-MS. Apremilast is an inhibitor of phosphodiesterase 4 (PDE4) with an IC50 value of 74 nM when tested in U937 cell lysates with 1 mM cAMP. It is orally active, significantly decreasing epidermal thickness and the epithelial cell proliferation index in a mouse model of psoriasis. Apremilast reduces both TNF-α and matrix metalloproteinase-3 production in gut lamina propria mononuclear cells from patients with inflammatory bowel disease. It also blocks spontaneous production of TNF-α from human rheumatoid synovial cells and improves the clinical score in mouse models of arthritis.