Pimecrolimusinhibitor of inflammatory cytokines secretion, cell-selective CAS# 137071-32-0 |
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Quality Control & MSDS
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| Cas No. | 137071-32-0 | SDF | Download SDF |
| PubChem ID | 6447131 | Appearance | Powder |
| Formula | C43H68ClNO11 | M.Wt | 810.45 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | SDZ-ASM 981 | ||
| Solubility | DMSO : ≥ 32 mg/mL (39.48 mM) *"≥" means soluble, but saturation unknown. | ||
| SMILES | CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)Cl)C)O)C)OC)OC)C)C | ||
| Standard InChIKey | KASDHRXLYQOAKZ-OLHLVPFQSA-N | ||
| Standard InChI | 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/b24-18-,26-20+/t25-,27+,28+,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Pimecrolimus is an immunophilin ligand, which binds specifically to the cytosolic receptor, immunophilin macrophilin-12.
Target: Others
Pimecrolimus blocks T-lymphocyte activation pathway by inhibiting calcineurin function [1]. Pimecrolimus prevents the release of cytokines and pro-inflammatory mediators from mast cells. Pimecrolimus binds to macrophilin-12, the pimecrolimusmacrophilin complex then binds to the cytosolic enzyme calcineurin phosphatase. The pimecrolimus-macrophilin complex prevents the dephosphorylation of the cytoplasmic component of the nuclear factor of activated T cells by inhibiting the action of calcineurin. Pimecrolimus inhibits not only the transcription and synthesis of cytokines from mast cells, but also the release of preformed mediators serotonin and β-hexosaminidase by the inhibition of Fcε-RI-mediated degranulation and secretion. Pimecrolimus treatment causes a strong down-regulation of the expression of mRNA for genes associated with the macrolactam target pathway and inflammation [2].
Pimecrolimus is found to be as effective as cyclosporine A following oral ingestion and slightly superior after subcutaneous administration in mice. Pimecrolimus contrasts cyclosporine A and tacrolimus by inhibiting ongoing secondary inflammatory response, but not impairing the primary immune response in allergic contact dermatitis in mice. [2] Pimecrolimus is as effective as the high-potency corticosteroid clobetasol-17-propionate in a pig model of allergic contact dermatitis (ACD). Pimecrolimus also effectively reduces skin inflammation and pruritus in hypomagnesemic hairless rats, a model that mimics acute signs of atopic dermatitis [3]. References: | |||||
Pimecrolimus Dilution Calculator
Pimecrolimus Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.2339 mL | 6.1694 mL | 12.3388 mL | 24.6776 mL | 30.8471 mL |
| 5 mM | 0.2468 mL | 1.2339 mL | 2.4678 mL | 4.9355 mL | 6.1694 mL |
| 10 mM | 0.1234 mL | 0.6169 mL | 1.2339 mL | 2.4678 mL | 3.0847 mL |
| 50 mM | 0.0247 mL | 0.1234 mL | 0.2468 mL | 0.4936 mL | 0.6169 mL |
| 100 mM | 0.0123 mL | 0.0617 mL | 0.1234 mL | 0.2468 mL | 0.3085 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Pimecrolimus is a cell-selective inhibitor of inflammatory cytokines secretion in T cells and mast cells [1].
Inflammatory cytokines are cytokines which promote systemic inflammation. Pimecrolimus can be used for the treatment of inflammatory skin diseases, such as plaque-type psoriasis, atopic dermatitis, irritant contact dermatitis and allergic contact dermatitis [1].
Pimecrolimus is a cell-selective inflammatory cytokines secretion inhibitor. Pimecrolimus inhibited the secretion of inflammatory cytokines in mast cells and T cells and also inhibited the release of preformed inflammatory mediators from mast cells. Pimecrolimus exhibited a low potential to impair systemic immune reactions in the skin [1]. In peripheral blood leukocytes contained basophil or mast cells, pimecrolimus inhibited histamine release induced by anti-IgE from basophils and mast cells by 82% and 73%, respectively. Also, pimecrolimus inhibited tryptase, LTC4 and TNF-alpha release [2]. In CD4+ T cells stimulated by dendritic cells (DC), pimecrolimus inhibited the up-regulation of CD25 and CD54 and surface expression of OX40. Pimecrolimus inhibited T cell proliferation with IC50 value of 0.55 nM and inhibited the synthesis of IFN-γ and TNF-α [3].
In treatment of allergic contact dermatitis (ACD) mice and rats, pimecrolimus exhibited a higher potency. In atopic dermatitis rats, pimecrolimus effectively reduced pruritus and skin inflammation [1].
References:
[1]. Stuetz A, Grassberger M, Meingassner JG. Pimecrolimus (Elidel, SDZ ASM 981)--preclinical pharmacologic profile and skin selectivity. Semin Cutan Med Surg, 2001, 20(4): 233-241.
[2]. Zuberbier T, Chong SU, Grunow K, et al. The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils. J Allergy Clin Immunol, 2001, 108(2): 275-280.
[3]. Kalthoff FS, Chung J, 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, 2002, 130(1): 85-92.
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Acute Pustular Dermatosis, Following Topical Treatment With Pimecrolimus, in a Child Affected With Atopic and Contact Hand Dermatitis.[Pubmed:26997932]
J Pediatr Pharmacol Ther. 2016 Jan-Feb;21(1):81-4.
Atopic dermatitis is considered an important risk factor for chronic hand dermatitis, which can be seen in children too. Pimecrolimus cream 1% is approved to treat atopic dermatitis in children aged 2 years or older. In adults, this drug has been used for some clinical indications other than atopic dermatitis, such as chronic hand dermatitis. Here, we describe an adverse drug reaction in a 2-year-old child affected with atopic dermatitis, who was treated with topical Pimecrolimus in order to ameliorate her concomitant hand dermatitis. The use of topical Pimecrolimus led to a previously undescribed hand pustular dermatosis, being consistent with a form of pustular leukocytoclastic vasculitis, which required the permanent discontinuation of topical Pimecrolimus.
Pimecrolimus increases the expression of interferon-inducible genes that modulate human coronary artery cells proliferation.[Pubmed:27212382]
Eur J Pharmacol. 2016 Aug 5;784:137-46.
The pharmacodynamics of the loaded compounds defines clinical failure or success of a drug-eluting device. Various limus derivatives have entered clinics due to the observed positive outcome after stent implantation, which is explained by their antiproliferative activity resulting from inhibition of the cytosolic immunophilin FK506-binding protein 12. Although Pimecrolimus also binds to this protein, Pimecrolimus-eluting stents failed in clinics. However, despite its impact on T lymphocytes little is known about the pharmacodynamics of Pimecrolimus in cultured human coronary artery cells. We were able to show that Pimecrolimus exerts antiproliferative activity in human smooth muscle and endothelial cells. Furthermore in those cells Pimecrolimus induced transcription of interferon-inducible genes which in part are known to modulate cell proliferation. Modulation of gene expression may be part of an interaction between calcineurin, the downstream target of the Pimecrolimus/FK506-binding protein 12-complex, and the toll-like receptor 4. In accordance are our findings showing that silencing of toll-like receptor 4 by siRNA in A549 a lung carcinoma cell line reduced the activation of interferon-inducible genes upon Pimecrolimus treatment in those cells. Based on our findings we hypothesize that calcineurin inhibition may induce the toll-like receptor 4 mediated activation of type I interferon signaling finally inducing the observed effect in endothelial and smooth muscle cells. The crosstalk of interferon and toll-like receptor signaling may be a molecular mechanism that contributed to the failure of Pimecrolimus-eluting stents in humans.
Pimecrolimus micelle exhibits excellent therapeutic effect for Keratoconjunctivitis Sicca.[Pubmed:26731192]
Colloids Surf B Biointerfaces. 2016 Apr 1;140:1-10.
Poor corneal penetration and short residence time on the ocular surface are two major bottlenecks for conventional ophthalmic formulations. To overcome the foregoing dilemmas, we prepared two novel formulations of Pimecrolimus nanomicelles (PNM) with particle size of 37.85 +/- 1.21 nm and thermosensitive hydrogel (PTH) for treating Keratoconjunctivitis Sicca (KCS). PNM were investigated by transmission electron microscopy (TEM), Malvern laser particle size analyzer, X-ray diffraction (XRD) system, and the content of drug in PNM was measured by high-performance liquid chromatography (HPLC). The drug loading and encapsulation efficiency reached to 7.57% +/- 0.10% and 97.9% +/- 1.26%, respectively. PTH displayed special gel-sol transition behavior with temperature increasing from 4 degrees C to 37 degrees C. The in vitro release profile demonstrated that PNM and PTH exhibited sustained-release behavior compared with free Pimecrolimus oil-based eye drop (FPO). In addition, we established a mouse model of KCS induced by benzalkonium chloride to evaluate the therapeutic outcome of different Pimecrolimus formulations. The production of tear, fluorescein staining scores and histopathologic examinations of the cornea were assessed in detail. The results confirmed that PNM had the best therapeutic effect among all formulations based on its higher drug encapsulation capability, favourable permeability and sustained release. All these indicated that PNM could serve as a potent ophthalmologic agent for KCS.
Annular Lichenoid Dermatitis of Youth: A Chronic Case Managed Using Pimecrolimus.[Pubmed:27653808]
Pediatr Dermatol. 2016 Nov;33(6):e360-e361.
Annular lichenoid dermatitis of youth, first described in 2003, is a rare and occasionally chronic skin disease. We report a case of annular lichenoid dermatitis of youth relapsing over the course of 5 years successfully treated and maintained with topical Pimecrolimus cream.
