Pimecrolimus

Chemodex
Product Code: CDX-P0598
Supplier: Chemodex
CodeSizePrice
CDX-P0598-M01010 mg£35.00
Quantity:
CDX-P0598-M05050 mg£108.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
+4°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
Elidel; SDZ-ASM 981; 33-Epichloro-33-desoxyascomycin
Appearance:
White to beige powder.
CAS:
137071-32-0
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Protect from light and moisture.
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
InChiKey:
KASDHRXLYQOAKZ-XDSKOBMDSA-N
Long Description:
Chemical. CAS: 137071-32-0. Formula: C43H68ClNO11. MW: 810.45. Synthetic. Pimecrolimus is a immunosuppressive natural ascomycin macrolactam that binds to macrophilin-12 (FKBP-12) and inhibits calcineurin as well as prolyl isomerase (rotamase). Presumably through these actions, it blocks the activation of T cells by allogeneic dendritic cells (IC50=0.55nM) without affecting dendritic cells. 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. These effects support the use of pimecrolimus in countering inflammatory skin diseases, such as atopic dermatitis (eczema) and psoriasis.
MDL:
MFCD00901792
Molecular Formula:
C43H68ClNO11
Molecular Weight:
810.45
Package Type:
Vial
Product Description:
Pimecrolimus is a immunosuppressive natural ascomycin macrolactam that binds to macrophilin-12 (FKBP-12) and inhibits calcineurin as well as prolyl isomerase (rotamase). Presumably through these actions, it blocks the activation of T cells by allogeneic dendritic cells (IC50=0.55nM) without affecting dendritic cells. 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. These effects support the use of pimecrolimus in countering inflammatory skin diseases, such as atopic dermatitis (eczema) and psoriasis.
Purity:
>97% (HPLC)
SMILES:
Cl[C@@H]1[C@@H](C[C@@H](CC1)/C=C(C)/[C@H]([C@H](C)[C@H](C2)O)OC([C@H](CCCC3)N3C(C([C@@](O)([C@H](C)C4)O[C@H]([C@H](C[C@@H](C)C/C(C)=C/[C@@H](CC)C2=O)OC)[C@H]4OC)=O)=O)=O)OC
Solubility Chemicals:
Soluble in DMSO (20mg/ml), DMF (20mg/ml) or ethanol (20mg/ml).
Source / Host:
Synthetic
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.

References

(1) D. Bochelen, et al.; J. Pharmacol. Exp. Therap. 288, 653 (1999) | (2) M. Grassberger, et al.; Br. J. Dermatol. 141, 264 (1999) | (3) T. Zuberbier, et al.; J. All. Clin. Immunol. 108, 275 (2001) | (4) F.S. Kalthoff, et al.; Clin. Exp. Immunol. 130, 85 (2002) | (5) K. Rappersberger, et al.; J. Invest. Dematol. 119, 876 (2002) | (6) J.G. Meingassner, et al.; J. Invest. Dermatol. 121, 77 (2003) | (7) F.S. Kalthoff, et al.; Clin. Exp. Immunol. 133, 350 (2003) | (8) J.G. Meingassner, et al.; Br. J. Dermatol. 149, 853 (2003) | (9) D.A. Plager, et al.; Int. Arch. Allergy Immunol. 149, 119 (2009) | (10) Z. Ma & Z. Jiao; Curr. Pharm. Des. 17, 3823 (2011) (Review) | (11) S.G. Danby & M.J. Cork; Br. J. Dermatol. 168, 235 (2013)