CAS 137071-32-0|Pimecrolimus

Introduction：Basic information about CAS 137071-32-0|Pimecrolimus, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Pimecrolimus BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

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	/
MSDS	ChineseUSA	Flash Point	477.6±37.1 °C

Names

Name	Pimecrolimus
Synonym	More Synonyms

Pimecrolimus BiologicalActivity

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	Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology
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.

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

Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology

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
InChIKey	KASDHRXLYQOAKZ-BJMBAXCKSA-N
SMILES	CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Cl)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC
Storage condition	-20°C Freezer

Safety Information

Hazard Codes	Xi
RIDADR	NONH for all modes of transport

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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