An immune modulator and a prodrug form of FTY720 phosphate
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Fingolimod

Item No. 11975

Technical Information
Formal Name
2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol
CAS Number
162359-55-9
Synonyms
  • FTY720
Molecular Formula
C19H33NO2
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/ml
λmax
218 nm
SMILES
OCC(N)(CO)CCC1=CC=C(CCCCCCCC)C=C1
InChi Code
InChI=1S/C19H33NO2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22/h9-12,21-22H,2-8,13-16,20H2,1H3
InChi Key
KKGQTZUTZRNORY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Fingolimod is an immune modulator, a prodrug form of the sphingosine-1-phosphate (S1P) receptor agonist FTY720 phosphate (Item No. 10008639), and a derivative of myriocin (Item No. 63150).1 It is converted by sphingosine kinase (SPHK) to FTY720 phosphate, which then acts as an agonist of S1P receptor 1 (S1P1), S1P3, S1P4, and S1P5, subsequently acting as a functional antagonist by inducing receptor internalization.1,2,3 Fingolimod (1 mg/kg) decreases the number of circulating lymphocytes in mice.4 It increases skin allograft survival in rats when administered at doses ranging from 0.3 to 3 mg/kg.5 Fingolimod (0.3 mg/kg) prevents disease development in a rat model of experimental autoimmune encephalomyelitis (EAE).1 It also inhibits S1P lyase when used at concentrations ranging from 0.3 to 30 µM.4 Formulations containing fingolimod have been used in the treatment of multiple sclerosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brinkmann, V., Davis, M.D., Heise, C.E., et alThe immune modulator FTY720 targets sphingosine 1-phosphate receptors. The Journal of Biological Chemisty 277(24), 21453-21457 (2002).

    2. Forrest, M., Sun, S.Y., Hajdu, R., et alImmune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes. J. Pharmacol. Exp. Ther. 309(2), 758-768 (2004).

    3. Brinkmann, V., Billich, A., Baumruker, T., et alFingolimod (FTY720): Discovery and development of an oral drug to treat multiple sclerosis. Nat. Rev. Drug Discov. 9(11), 883-897 (2010).

    4. Bandhuvula, P., Tam, Y.Y., Oskouian, B., et alThe immune modulator FTY720 inhibits sphingosine-1-phosphate lyase activity. The Journal of Biological Chemisty 280(40), 33697-33700 (2005).

    5. Shimizu, H., Takahashi, M., Kaneko, T., et alKRP-203, a novel synthetic immunosuppressant, prolongs graft survival and attenuates chronic rejection in rat skin and heart allografts. Circulation 111(2), 222-229 (2005).

    Product Citations

    Grenald, S.A., Doyle, T.M., Zhang, H., et alTargeting the S1P/S1PR1 axis mitigates cancer-induced bone pain and neuroinflammation. Pain 158(9), 1733-1742 (2017).

    Harris, C.M., Mittelstadt, S., Banfor, P., et alSphingosine-1-phosphate (S1P) lyase inhibition causes increased cardiac S1P levels and bradycardia in rats. J. Pharmacol. Exp. Ther. 359(1), 151-158 (2016).