An active metabolite of apremilast
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Parent Compound(s)
18502Apremilast
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O-Demethyl Apremilast

Item No. 34216

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-[(1S)-1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-acetamide
CAS Number
1384441-38-6
Synonyms
  • 4'-hydroxy APR
Molecular Formula
C21H22N2O7S
Formula Weight
446.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml
λmax
231 nm
SMILES
CS(C[C@H](C1=CC(OCC)=C(C=C1)O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)(=O)=O
InChi Code
InChI=1S/C21H22N2O7S/c1-4-30-18-10-13(8-9-17(18)25)16(11-31(3,28)29)23-20(26)14-6-5-7-15(22-12(2)24)19(14)21(23)27/h5-10,16,25H,4,11H2,1-3H3,(H,22,24)/t16-/m1/s1
InChi Key
PEUJABWEZWJNBO-MRXNPFEDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

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    Cayman Chemical
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    Product Description

    O-Demethyl apremilast is an active metabolite of the phosphodiesterase 4 (PDE4) inhibitor apremilast (Item No. 18502).1 It inhibits the activity of PDE4 isolated from U937 cells and LPS-induced TNF-α production in isolated human peripheral blood mononuclear cells (PBMCs; IC50s = 8.3 and 5.6 µM, respectively). O-Demethyl apremilast is also an oxidative degradation product of apremilast.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoffmann, M., Kumar, G., Schafer, P., et al. Disposition, metabolism and mass balance of [14C]apremilast following oral administration. Xenobiotica 41(12), 1063-1075 (2011).

    2. Lu, Y., Shen, X., Hang, T., et al. Identification and characterization of process-related substances and degradation products in apremilast: Process optimization and degradation pathway elucidation. J. Pharm. Biomed. Anal. 141, 70-78 (2017).

    3. Bhole, R.P., Naksakhare, S.R., and Bonde, C.G. A stability indicating HPTLC method for apremilast and identification of degradation products using MS/MS. J. Pharm. Sci. & Res. 11(5), 1861-1869 (2019).