Anti-inflammatory macrolactam
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Pimecrolimus

Item No. 13107

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9E)-3S-[(1E)-2-[(1R,3R,4S)-4R-chloro-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5S,6,8R,11,12S,13,14S,15R,16S,17,18R,19R,24,25,26,26aS-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
CAS Number
137071-32-0
Synonyms
  • Elidel
  • SDZ-ASM 981
Molecular Formula
C43H68ClNO11
Formula Weight
810.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
CO[C@@H]1[C@]([C@H](C[C@H](C/C(C)=C\[C@H](C(C[C@H](O)[C@H]2C)=O)CC)C)OC)([H])O[C@@](O)(C(C(N(CCCC3)[C@]3([H])C(O[C@@H]2/C(C)=C/[C@H](CC[C@@H]4Cl)C[C@H]4OC)=O)=O)=O)[C@H](C)C1
InChi Code
InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-
InChi Key
KASDHRXLYQOAKZ-OLHLVPFQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Cayman Chemical
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    Product Description

    Pimecrolimus is a natural ascomycin macrolactam that binds to macrophilin-12 (FKBP-12) and inhibits calcineurin as well as prolyl isomerase (rotamase).1 Presumably through these actions, it blocks the activation of T cells by allogeneic dendritic cells (IC50 = 0.55 nM) without affecting dendritic cells.2,3,4,5 Moreover, pimecrolimus suppresses the generation of pro-inflammatory cytokines by T cells, the release of pre-formed inflammatory mediators from mast cells, and the activation of eosinophils.6,2,7 These effects support the use of pimecrolimus in countering inflammatory skin diseases, such as atopic dermatitis (eczema) and psoriasis.8,9,10

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bochelen, D., Rudin, M., and Sauter, A. Calcineurin inhibitors FK506 and SDZ ASM 981 alleviate the outcome of focal cerebral ischemic/reperfusion injury. J. Pharmacol. Exp. Ther. 288(2), 653-659 (1999).

    2. Kalthoff, F.S., Chung, J., and Stuetz, A. Pimecrolimus inhibits up-regulation of OX40 and synthesis of inflammatory cytokines upon secondary T cell activation by allogeneic dendritic cells. Clin. Exp. Immunol. 130, 85-92 (2002).

    3. Meingassner, J.G., Kowalsky, E., Schwendinger, H., et al. Pimecrolimus does not affect Langerhans cells in murine epidermis. Br. J. Dermatol. 149, 853-857 (2003).

    4. Kalthoff, F.S., Chung, J., Musser, P., et al. Pimecrolimus does not affect the differentiation, maturation and function of human monocyte-derived dendritic cells, in contrast to corticosteroids. Clin. Exp. Immunol. 133, 350-359 (2003).

    5. Meingassner, J.G., Fahrngruber, H., and Bavandi, A. Pimecrolimus inhibits the elicitation phase but does not suppress the sensitization phase in murine contact hypersensitivity, in contrast to tacrolimus and cyclosporine A. J. Invest. Dermatol. 121(1), 77-80 (2003).

    6. Grassberger, M., Baumruker, T., Enz, A., et al. A novel anti-inflammatory drug, SDZ ASM 981, for the treatment of skin diseases: In vitro pharmacology. Br. J. Dermatol. 141, 264-273 (1999).

    7. Plager, D.A., Henke, S.A., Matsuwaki, Y., et al. Pimecrolimus reduces eosinophil activation associated with calcium mobilization. Int. Arch. Allergy Immunol. 149, 119-126 (2009).

    8. Rappersberger, K., Komar, M., Ebelin, M.E., et al. Pimecrolimus identifies a common genomic anti-inflammatory profile, is clinically highly effective in psoriasis and is well tolerated. J. Invest. Dermatol. 119(4), 876-887 (2002).

    9. Allen, B.R., Lakhanpaul, M., Morris, A., et al. Systemic exposure, tolerability, and efficacy of pimecrolimus cream 1% in atopic dermatitis patients. Arch. Dis. Child. 88, 969-973 (2003).

    10. Walling, H.W., and Swick, B.L. Update on the management of chronic eczema: New approaches and emerging treatment options. Clin. Cosmet. Investig. Dermatol. 3, 99-117 (2010).