API reference
Pimecrolimus
- CAS number
- 137071-32-0
- Molecular formula
- C43H68ClNO11
- Molecular weight
- 810.4 g/mol
About this molecule
Pimecrolimus is a 33-epi-chloro-derivative of the ascomycin macrolactam with immunosuppressant property. Pimecrolimus binds to the receptor macrophilin-12 (FKBP-12) forming a complex that blocks the calcium-dependent signal transduction cascade mediated by calcineurin. Via dephosphorylation, calcineurin is the enzyme responsible for activating nuclear factor of activated T-cells (NF-AT), a T cell transcriptional regulatory factor. As a consequence, the synthesis and release of Th1- (T helper 1) and Th2- (T helper 2) type cytokines, and other inflammatory mediators from T-cells and mast cells are blocked and the expression of signals essential for the activation of inflammatory T-lymphocytes is inhibited. However, pimecrolimus mode of action is cell-selective and does not affect Langerhans' cells/dendritic cells and primary fibroblasts.
Source: NCI Thesaurus (NCIt), via PubChem.
Identifiers
- IUPAC name
- (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
- InChIKey
- KASDHRXLYQOAKZ-XDSKOBMDSA-N
- SMILES
- CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\C
- PubChem CID
- 6509979
Also known as
Pimecrolimus · Elidel · SDZ-ASM 981 · SDZ ASM 981 · 33-epi-Chloro-33-desoxyascomycin · Pimecrolimusum · (-)-PIMECROLIMUS · D11AX15
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