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Pimecrolimus

CAT: 0013-GTR19163384-02Size: 1 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19163384-02Size:1 g
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Description
Pimecrolimus, like all ascomycins, is an immunophilin ligand, which binds specifically to the cytosolic receptor, immunophilin macrophilin-12. (In Vitro) :Pimecrolimus (SDZ-ASM 981) (100 nM) targets T-cells and mast cells and inhibits the production and release of cytokines and other inflammatory mediators, as well as the expression of signals essential for the activation of inflammatory T-lymphocytes.Pimecrolimus acts specifically on cells that are crucial for the effector phase of an inflammatory reaction.Pimecrolimus (10 nM; 3 days) inhibits the polyclonal growth of peripheral blood T cells in murine and human mixed lymphocyte reactions.Pimecrolimus inhibits cytokine IL-2, IL-4, IL-10 and interferon-γ release from T-cell clone CFTS4:3.1 with IC50s of 0.28, 0.3, 0.2 and 0.42 nM, respectively after antigen-specific stimulation. (In Vivo) :Pimecrolimus (SDZ-ASM 981) (0-0.4%; topical; 10 μL once) inhibits allergic contact dermatitis in mice and pigs.Pimecrolimus (0-90 mg/kg; p.o. or s.c.; twice or once) potently inhibits allergic contact dermatitis in mice and rats.
CAS Number
137071-32-0
Product Name Alternative
Elidel | SDZ-ASM 981
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
Ethanol: 100 mg/mL (123.38 mM) ; DMSO: 100 mg/mL (123.38 mM)
Smiles
O=C (C (N1CCCC[C@@]1 ([H]) C (O[C@H] (/C (C) =C/[C@H]2C[C@@H] (OC) [C@@H] (Cl) CC2) [C@H] (C) [C@@H] (O) C3) =O) =O) [C@@] (O4) (O) [C@H] (C) C[C@H] (OC) [C@@]4 ([H]) [C@@H] (OC) C[C@@H] (C) C/C (C) =C/[C@@H] (CC) C3=O
Molecular Formula
C43H68ClNO11
Molecular Weight
810.45
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(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.

Chemical Information

Pimecrolimus

Pimecrolimus is a lactam and a macrolide.

CAS Number137071-32-0
PubChem CID6509979
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
Molecular FormulaC43H68ClNO11
Molecular Weight810.4
XLogP3.8
Topological Polar Surface Area158
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count6
Heavy Atom Count56
Formal Charge0
Complexity1440
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
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
Chemical Structure
2D Structure
2D structure of Pimecrolimus
CAS: 137071-32-0
CID: 6509979
Formula: C43H68ClNO11
MW: 810.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight810.4
XLogP33.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count6
Exact Mass809.4480897
Monoisotopic Mass809.4480897
Topological Polar Surface Area158 Ų
Heavy Atom Count56
Formal Charge0
Complexity1440
Isotope Atom Count0
Defined Atom Stereocenter Count14
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
B1817-5.1Pimecrolimus
B1817-50(-) -Pimecrolimus

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