An immunosuppressant
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Isomer(s)
20391PSC 833
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Voclosporin

Item No. 39719

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6,8-nonadienoic acid]-cyclosporin A
CAS Number
515814-01-4
Synonyms
  • (E)-ISA247
  • ISATX247
  • LX211
  • R-15424
  • trans-ISA 247
Molecular Formula
C63H111N11O12
Formula Weight
1214.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
C=C/C=C/C[C@@H](C)[C@H]([C@]1([H])N(C([C@@H](N(C([C@@H](N(C([C@@H](N(C([C@H](NC([C@@H](NC([C@@H](N(C([C@@H](NC([C@@H](N(C(CN(C([C@@H](NC1=O)CC)=O)C)=O)C)CC(C)C)=O)C(C)C)=O)C)CC(C)C)=O)C)=O)C)=O)C)CC(C)C)=O)C)CC(C)C)=O)C)C(C)C)=O)C)O
InChi Code
InChI=1S/C63H111N11O12/c1-25-27-28-29-41(15)53(76)52-57(80)66-44(26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27-28,35-48,50-53,76H,1,26,29-34H2,2-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b28-27+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1
InChi Key
BICRTLVBTLFLRD-PTWUADNWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Voclosporin is an immunosuppressant and a derivative of cyclosporin A (Item No. 12088).1,2 It binds to cyclophilin A (Kd = 15 nM) and inhibits calcineurin activity in isolated human whole blood (IC50 = 120 ng/ml). Voclosporin reduces the proliferation of, and production of IL-2, IFN-γ, and TNF-α in, isolated cynomolgus monkey lymphocytes (EC50s = 202.79, 135.32, 177.11, and 138.56 ng/ml, respectively).3 It decreases disease severity in a rat model of experimental autoimmune uveoretinitis induced by interphotoreceptor retinoid-binding protein (IRBP), also known as retinoid binding protein 3 (RBP3), when administered at doses ranging from 2.5 to 40 mg/kg.4 Voclosporin (1.75 mg/kg) increases graft survival in a rat model of heterotopic heart transplantation.2 Unlike cyclosporin A, voclosporin does not increase serum creatinine levels in rabbits. Voclosporin also inhibits the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in infected Calu-3 cells in a concentration-dependent manner.5 Formulations containing voclosporin have been used in the treatment of lupus nephritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kuglstatter, A., Mueller, F., Kusznir, E.A., et al. Structural basis for the cyclophilin A binding affinity and immunosuppressive potency of E-ISA247 (voclosporin). Acta Crystallogr. D Biol. Crystallogr. 67(Pt. 2), 119-123 (2011).

    2. Aspeslet, L., Freitag, D., Trepanier, D., et al. ISATX247: A novel calcineurin inhibitor. Transplant. Proc. 33(1-2), 1048-1051 (2001).

    3. Bîrsan, T., Dambrin, C., Freitag, D.G., et al. The novel calcineurin inhibitor ISA247: A more potent immunosuppressant than cyclosporine in vitro. Transpl. Int. 17(12), 767-771 (2005).

    4. Cunningham, M.A., Austin, B.A., Li, Z., et al. LX211 (voclosporin) suppresses experimental uveitis and inhibits human T cells. Invest. Ophthalmol. Vis. Sci. 50(1), 249-255 (2009).

    5. Ogando, N.S., Metscher, E., Moes, D.J.A.R., et al. The cyclophilin-dependent calcineurin inhibitor voclosporin inhibits SARS-CoV-2 replication in cell culture. Transpl. Int. 35, 10369 (2022).