Pimecrolimus

Pimecrolimus is an immunomodulating agent used in the treatment of atopic dermatitis (eczema).

Product information

CAS Number: 137071-32-0

Molecular Weight: 810.45

Formula: C43H68ClNO11

Synonym:

ASM-981

ASM981

ASM 981

SDZ ASM 981

SDZ-ASM 981

SDZ-ASM-981

Pimecrolimusum

33-epi-Chloro-33-desoxyascomycin

Aregen

Rizan

Elidel

Chemical Name: (1R, 9S, 12S, 13R, 14S, 17R, 18E, 21S, 23S, 24R, 25S, 27R)-12-[(1E)-2{(1R, 3R, 4S)-4-chloro-3-methoxycyclohexyl}-1-methylvinyl]-17-ethyl-1, 14-dihydroxy-23, 25 dimethoxy-13, 19, 21, 27-tetramethyl-11, 28-dioxa-4-aza-tricyclo[22.3.1.0 4, 9]octacos-18-ene2, 3, 10, 16-tetraone.

Smiles: CC[C@@H]1C=C(C)C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@H](C)C[C@@H]2OC)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@@H]([C@H](C)[C@@H](O)CC1=O)/C(/C)=C/[C@H]1C[C@@H](OC)[C@@H](Cl)CC1 |c:3|

InChiKey: KASDHRXLYQOAKZ-OLHLVPFQSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 100 mg/mL(123.38 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Pimecrolimus blocks T-lymphocyte activation pathway by inhibiting calcineurin function. 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 Fc∈-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.

In Vivo:

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. 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. Pimecrolimus shows only a low potential to impair systemic immune responses when compared with tacrolimus as shown in rats in (1) the localized graft-versus-host reaction, (2) the antibody formation to sheep red blood cells, and (3) kidney transplantation.

References:

1. Stuetz A, et al. Semin Cutan Med Surg, 2001, 20(4), 233-241.
2. Gupta AK, et al. J Eur Acad Dermatol Venereol, 2003, 17(5), 493-503.
3. Nghiem P, et al. Am Acad Dermatol, 2002, 46(2), 228-241.

Products are for research use only. Not for human use.