Pimecrolimus

Modify Date: 2024-01-02 17:45:28

Pimecrolimus Structure
Pimecrolimus structure
 Common Name Pimecrolimus
CAS Number 137071-32-0 Molecular Weight 810.453
Density 1.2±0.1 g/cm3 Boiling Point 866.1±75.0 °C at 760 mmHg
Molecular Formula C43H68ClNO11 Melting Point N/A
MSDS Chinese USA Flash Point 477.6±37.1 °C

 Use of Pimecrolimus


Pimecrolimus is an immunophilin ligand, which binds specifically to the cytosolic receptor, immunophilin macrophilin-12.Target: OthersPimecrolimus blocks T-lymphocyte activation pathway by inhibiting calcineurin function [1]. 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 Fcε-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 [2].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. [2] 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 [3].

 Names

Name Pimecrolimus
Synonym More Synonyms

 Pimecrolimus Biological Activity

Description Pimecrolimus is an immunophilin ligand, which binds specifically to the cytosolic receptor, immunophilin macrophilin-12.Target: OthersPimecrolimus blocks T-lymphocyte activation pathway by inhibiting calcineurin function [1]. 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 Fcε-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 [2].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. [2] 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 [3].
Related Catalog
References

[1]. Nghiem, P., G. Pearson, and R.G. Langley, Tacrolimus and pimecrolimus: from clever prokaryotes to inhibiting calcineurin and treating atopic dermatitis. J Am Acad Dermatol, 2002. 46(2): p. 228-41.

[2]. Gupta, A.K. and M. Chow, Pimecrolimus: a review. J Eur Acad Dermatol Venereol, 2003. 17(5): p. 493-503.

[3]. Stuetz, A., M. Grassberger, and J.G. Meingassner, Pimecrolimus (Elidel, SDZ ASM 981)--preclinical pharmacologic profile and skin selectivity. Semin Cutan Med Surg, 2001. 20(4): p. 233-41.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 866.1±75.0 °C at 760 mmHg
Molecular Formula C43H68ClNO11
Molecular Weight 810.453
Flash Point 477.6±37.1 °C
Exact Mass 809.448120
PSA 158.13000
LogP 5.08
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.543
Storage condition -20°C Freezer

 Safety Information

Hazard Codes Xi
RIDADR NONH for all modes of transport

 Synthetic Route

Tacrolimus Related Compound A structure

Tacrolimus Rela...

CAS#:135635-46-0

~47%

Pimecrolimus Structure

Pimecrolimus

CAS#:137071-32-0

Literature: Grassberger, Maximilian; Horvath, Amarylla Patent: US2008/71082 A1, 2008 ; Location in patent: Page/Page column 3 ;
N/A structure

N/A

CAS#:148146-56-9

~%

Pimecrolimus Structure

Pimecrolimus

CAS#:137071-32-0

Literature: WO2006/60614 A1, ; Page/Page column 13 ;
24-O-acetyl-pimecrolimus structure

24-O-acetyl-pim...

CAS#:1178863-99-4

~39%

Pimecrolimus Structure

Pimecrolimus

CAS#:137071-32-0

Literature: Ferraboschi, Patrizia; Colombo, Diego; De Mieri, Maria; Grisenti, Paride Tetrahedron Letters, 2009 , vol. 50, # 30 p. 4384 - 4388

 Precursor & DownStream

Precursor  2

DownStream  0

 Synonyms

Pimecrolimus
Elidel,SDZ-ASM-981
33-epi-33-chloro-FR 520
SDZ-ASM 981
Elidel
33-epi-chloro-33-desoxy-ascomycin
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-{(1E)-1-[(1R,3R,4S)-4-Chloro-3-methoxycyclohexyl]-1-propen-2-yl}-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatri ;cyclo[22.3.1.0]octacos-18-ene-2,3,10,16-tetrone
15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 3-[(E)-2-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-
Picrolimus
ASM 981
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