A phosphodiesterase-4 inhibitor
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Enantiomer(s)
31111(−)-Rolipram
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(±)-Rolipram

Item No. 10011132

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
CAS Number
61413-54-5
Synonyms
  • SB 95952
  • ZK 62711
Molecular Formula
C16H21NO3
Formula Weight
275.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS (pH 7.2) (1:9): 0.5 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/ml
λmax
231, 280 nm
SMILES
COC(C=CC(C1CC(NC1)=O)=C2)=C2OC3CCCC3
InChi Code
InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
InChi Key
HJORMJIFDVBMOB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    (±)-Rolipram is a cell-permeable selective PDE4 inhibitor. Since PDE4 is abundant in leukocytes, (±)-rolipram inhibits inflammation by suppressing leukocyte function, inhibiting C5a-stimulated LTC4 synthesis in eosinophils (IC50 = 200 nM),1 and lipopolysaccharide-induced TNF synthesis in monocytes (IC50 = 360 nM).2 (±)-Rolipram also enhances neuronal survival,3 has antipsychotic effects in mice,4 and suppresses bone loss in ovariectomized rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tenor, H., Hatzelmann, A., Church, M.K., et al. Effects of theophylline and rolipram on leukotriene C4 (LTC4) synthesis and chemotaxis of human eosinophils from normal and atopic subjects. Br. J. Pharmacol. 118(7), 1727-1735 (1996).

    2. Souness, J.E., Griffin, M., Maslen, C., et al. Evidence that cyclic AMP phosphodiesterase inhibitors suppress TNFα generation from human monocytes by interacting with a 'low-affinity' phosphodiesterase 4 conformer. Br. J. Pharmacol. 118(3), 649-658 (1996).

    3. Sasaki, T., Kitagawa, K., Omura-Matsuoka, E., et al. The phosphodiesterase inhibitor rolipram promotes survival of newborn hippocampal neurons after ischemia. Stroke 38(5), 1597-1605 (2007).

    4. Kanes, S.J., Tokarczyk, J., Siegel, S.J., et al. Rolipram: A specific phosphodiesterase 4 inhibitor with potential antipsychotic activity. Neuroscience 144(1), 239-246 (2007).

    5. Yao, W., Tian, X.Y., Chen, J., et al. Rolipram, a phosphodiesterase 4 inhibitor, prevented cancellous and cortical bone loss by inhibiting endosteal bone resorption and maintaining the elevated periosteal bone formation in adult ovariectomized rats. J. Musculoskelet. Neuronal. Interact. 7(2), 119-130 (2007).