(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

• ChemBase ID: 73075
• Molecular Formular: C43H68ClNO11
• Molecular Mass: 810.45312
• Monoisotopic Mass: 809.44808968
• SMILES: [C@H]1(C[C@@H](CC[C@@H]1Cl)/C=C(/[C@@H]1[C@@H]([C@@H](O)CC(=O)[C@H](CC)/C=C(/C[C@@H](C[C@@H]([C@H]2O[C@@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)([C@@H](C[C@@H]2OC)C)O)OC)C)\C)C)\C)OC
• Canonical SMILES: CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@@H](C[C@@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@@H]([C@@H](C1)OC)Cl)/C)CCCC2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone
• IUPAC Traditional name: pimecrolimus
• Synonyms: Elidel; SDZ-ASM-981; Pimecrolimus

Database IDs

• CAS Number: 137071-32-0
• PubChem SID: 162037995
• PubChem CID: 6509979

CALCULATED PROPERTIES

• Acid pKa: 9.955626
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 6.808116
• LogD (pH = 7.4): 6.806926
• Log P: 6.808131
• Molar Refractivity: 214.0262 cm^3
• Polarizability: 84.57097 Å^3
• Polar Surface Area: 158.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S5004

Research Area: Inflammation
Biological Activity:
Pimecrolimus caused a strong and dose-dependent inhibition of anti-IgE–induced release of histamine from mast cells and basophils (maximally 73% and 82%, respectively, at 500 nmol/L pimecrolimus) and of mast cell tryptase (maximally 75%) and a less pronounced inhibition of LTC4 (maximally 32%) and of calcium ionophore plus phorbol myristate acetate–induced mast cell TNF-α release (90% maximum at 100 nmol/L pimecrolimus). [1]In the pig model, topical SDZ ASM 981 was as effective as the ultrapotent corticosteroid clobetasol-17-propionate, and when compared with a series of commercial topical corticosteroid preparations, 0.1% SDZ ASM 981 had equivalent efficacy to clobetasol-17-propionate (0.05%), the most potent product on the market. Unlike the corticosteroid, however, SDZ ASM 981 did not cause skin atrophy in pigs. [2]SDZ ASM 981 inhibits the proliferation of human T cells after antigen-specific or non-specific stimulation. It downregulates the production of Th1 [interleukin (IL)-2, interferon-γ] and Th2 (IL-4, IL-10) type cytokines after antigen-specific stimulation of a human T-helper cell clone isolated from the skin of an atopic dermatitis patient. SDZ ASM 981 inhibits the phorbol myristate acetate/phytohaemagglutinin-stimulated transcription of a reporter gene coupled to the human IL-2 promoter in the human T-cell line Jurkat and the IgE/antigen-mediated transcription of a reporter gene coupled to the human tumour necrosis factor (TNF)-α promoter in the murine mast-cell line CPII. [3]