A formyl peptide receptor antagonist
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Cyclosporin H

Item No. 17182

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(N-methyl-D-valine)-cyclosporin A
CAS Number
83602-39-5
Synonyms
  • 5-(N-methyl-D-valine)-Cyclosporin A
  • Sandoz 37-839
Molecular Formula
C62H111N11O12
Formula Weight
1202.6
Purity
≥95%
Formulation (Request formulation change)
A white powder
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
O[C@@H]([C@](C(N[C@H](C(N(CC(N(C)[C@H](C(N[C@@H](C(C)C)C(N(C)[C@H]1CC(C)C)=O)=O)CC(C)C)=O)C)=O)CC)=O)([H])N(C([C@@H](C(C)C)N(C([C@@H](N(C([C@H](CC(C)C)N(C([C@H](NC([C@@H](NC1=O)C)=O)C)=O)C)=O)C)CC(C)C)=O)C)=O)C)[C@H](C)C/C=C/C
InChi Code
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(3
InChi Key
PMATZTZNYRCHOR-JLPRAAIDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $40

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    5 mg

    $109

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    10 mg

    $198

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    Product Description

    Cyclosporin H is a natural cyclic undecapeptide that selectively antagonizes the formyl peptide receptor at concentrations ranging from 0.1 to 10 µM.1,2,3 Unlike cyclosporin A (Item No. 12088), cyclosporin H does not bind cyclophilin to evoke an immunosuppressant response.4 Cyclosporin H has been reported to inhibit phorbol ester-mediated effects in mouse skin and block calcium/calmodulin-dependent EF-2 phosphorylation in vitro.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wenzel-Seifert, K., and Siefert, R. Cyclosporin H is a potent and selective formyl peptide receptor antagonist. Comparison with N-t-butoxycarbonyl-L-phenylalanyl-L-leucyl-L-phenylalanyl-L- leucyl-L-phenylalanine and cyclosporins A, B, C, D, and E. J. Immunol. 150(10), 4591-4599 (1993).

    2. Yan, P., Nanamori, M., Sun, M., et al. The immunosuppressant cyclosporin A antagonizes human formyl peptide receptor through inhibition of cognate ligand binding. J. Immunol. 177(10), 7050-7058 (2006).

    3. Zhou, C., Zhou, Y., Wang, J., et al. V101L of human formyl peptide receptor 1 (FPR1) increases receptor affinity and augments the antagonism mediated by cyclosporins. Biochem. J. 451(2), 245-255 (2013).

    4. Sherry, B., Yarlett, N., Strupp, A., et al. Identification of cyclophilin as a proinflammatory secretory product of lipopolysaccharide-activated macrophages. Proc. Natl. Acad. Sci. USA 89(8), 3511-3515 (1992).

    5. Gschwendt, M., Kittstein, W., and Marks, F. The weak immunosuppressant cyclosporine D as well as the immunologically inactive cyclosporine H are potent inhibitors in vivo of phorbol ester TPA-induced biological effects in mouse skin and of Ca2+/calmodulin dependent EF-2 phosphorylation in vitro. Biochem. Biophys. Res. Commun. 150(2), 545-551 (1988).