The inactive enantiomer of a potent anti-inflammatory
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Product Type

Biochemicals

Research Area

(S)-Lisofylline

Item No. 13617

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,7-dihydro-1-[5S-hydroxyhexyl]-3,7-dimethyl-1H-purine-2,6-dione
CAS Number
100324-80-9
Synonyms
  • (+)-Lisofylline
  • (S)-LSF
Molecular Formula
C13H20N4O3
Formula Weight
280.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 3 mg/mlEthanol: 15 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
273 nm
SMILES
O=C(N(C)C1=C2N(C)C=N1)N(CCCC[C@@H](O)C)C2=O
InChi Code
InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m0/s1
InChi Key
NSMXQKNUPPXBRG-VIFPVBQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    (S)-LSF is the pharmacologically inactive optical enantiomer of (R)-LSF, the biologically active isomer.1 When metabolized by isolated human liver cells, pentoxifylline is exclusively reduced to (S)-LSF in the cytosol, while reduction in liver microsomes is 85% stereoselective in favor of (S)-LSF formation.2 Thus, pentoxifylline is an inefficient prodrug for the delivery of therapeutically relevant lisofylline.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wyska, E., Pekala, E., and Szymura-Oleksiak, J. Interconversion and tissue distribution of pentoxifylline and lisofylline in mice. Chirality 18(8), 644-651 (2006).

    2. Lillibridge, J.A., Kalhorn, T.F., and Slattery, J.T. Metabolism of lisofylline and pentoxifylline in human liver microsomes and cytosol. Drug Metab. Dispos. 24(11), 1174-1179 (1996).