Elidel

Pimecrolimus

Clinical data
Trade names	Elidel
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	topical
ATC code	D11AH02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	low systemic absorption
Protein binding	74%–87%
Metabolism	Hepatic CYP3A
Identifiers
IUPAC name (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)
CAS Number	137071-32-0 Y
PubChem CID	16051947
DrugBank	DB00337 Y
ChemSpider	10482089 Y
UNII	7KYV510875
ChEMBL	CHEMBL1200686 N
ECHA InfoCard	100.124.895
Chemical and physical data
Formula	C43H68ClNO11
Molar mass	810.453 g/mol
3D model (JSmol)	Interactive image
SMILES Cl[C@@H]1CC[C@H](C[C@H]1OC)\C=C(/C)[C@H]2OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@]3(O)O[C@H]([C@H](C[C@@H](C)CC(\C)=C\[C@@H](CC)C(=O)C[C@H](O)[C@H]2C)OC)[C@@H](OC)C[C@H]3C
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 Y Key:KASDHRXLYQOAKZ-ZPSXYTITSA-N Y
NY (what is this?)

Pimecrolimus is an immunomodulating agent of the calcineurin inhibitor class used in the treatment of atopic dermatitis (eczema). It is available as a topical cream, once marketed by Novartis (however, Galderma has been promoting the compound in Canada since early 2007) under the trade name Elidel.

Pimecrolimus is an ascomycin macrolactam derivative. It has been shown in vitro that pimecrolimus binds to macrophilin-12 (also referred to as FKBP-12) and inhibits calcineurin. Thus pimecrolimus inhibits T-cell activation by inhibiting the synthesis and release of cytokines from T-cells. Pimecrolimus also prevents the release of inflammatory cytokines and mediators from mast cells.

Pimecrolimus, like tacrolimus, belongs to the ascomycin class of macrolactam immunosuppressives, acting by the inhibition of T-cell activation by the calcineurin pathway and inhibition of the release of numerous inflammatory cytokines, thereby preventing the cascade of immune and inflammatory signals. Pimecrolimus has a similar mode of action to that of tacrolimus but is more selective, with no effect on dendritic (Langerhans) cells. It has lower permeation through the skin than topical steroids or topical tacrolimus although they have not been compared with each other for their permeation ability through mucosa. In addition, in contrast with topical steroids, pimecrolimus does not produce skin atrophy.

It has been proven to be effective in various inflammatory skin diseases, e.g., seborrheic dermatitis,cutaneous lupus erythematosus,oral lichen planus,vitiligo, and psoriasis. Tacrolimus and pimecrolimus are both calcineurin inhibitors and function as immunosuppressants.