Pimecrolimus

For research use only. Not for therapeutic Use.

  • CAT Number: A000429
  • CAS Number: 137071-32-0
  • Molecular Formula: C₄₃H₆₈ClNO₁₁
  • Molecular Weight: 810.45
  • Purity: ≥95%
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Pimecrolimus is an immunomodulating agent used in the treatment of atopic dermatitis (eczema). It is currently available as a topical cream, once marketed by Novartis (however Galderma is promoting the compound in Canada since early 2007) under the trade name Elidel. Pimecrolimus is an ascomycin macrolactam derivative. It has been shown in vitro that pimecrolimus binds to macrophilin-12(also referred to as FKBP-12) and inhibits calcineurin. Thus pimecrolimus inhibits T-cell activation by inhibiting the synthesis and release of cytokines from T-cells. Pimecrolimus also prevents the release of inflammatory cytokines and mediators from mast cells.


Catalog Number A000429
CAS Number 137071-32-0
Synonyms

Elidel; 137071-32-0; Pimecrolimus(Elidel); SDZ ASM 981; SDZ-ASM-981

Molecular Formula C₄₃H₆₈ClNO₁₁
Purity ≥95%
Storage -20°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-,2
InChIKey KASDHRXLYQOAKZ-OLHLVPFQSA-N
SMILES CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)Cl)C)O)C)OC)OC)C)C
Reference

1: Sigurgeirsson B, Luger T. A 5-year randomized trial on the safety and efficacy
of pimecrolimus in atopic dermatitis: a critical appraisal – author response. Br
J Dermatol. 2017 Oct;177(4):1006. doi: 10.1111/bjd.15849. Epub 2017 Sep 21.
PubMed PMID: 28940181.
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2: Weidinger S, Baurecht H, Schmitt J. A 5-year randomized trial on the safety
and efficacy of pimecrolimus in atopic dermatitis: a critical appraisal. Br J
Dermatol. 2017 Oct;177(4):999-1003. doi: 10.1111/bjd.15827. Epub 2017 Sep 4.
PubMed PMID: 28868633.

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3: Charman C. A 5-year randomized trial on the safety and efficacy of
pimecrolimus in atopic dermatitis: a critical appraisal – comment. Br J Dermatol.
2017 Oct;177(4):1004-1005. doi: 10.1111/bjd.15848. Epub 2017 Aug 31. PubMed PMID:
28858382.

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4: Zhao J, Sun W, Zhang C, Wu J, Le Y, Huang C, Liu Y, Xiang L. Comparison of
different regimens of pimecrolimus 1% cream in the treatment of facial seborrheic
dermatitis. J Cosmet Dermatol. 2017 Jun 7. doi: 10.1111/jocd.12353. [Epub ahead
of print] PubMed PMID: 28589618.
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5: Xu P, Chen J, Tan C, Lai RS, Min ZS. Pimecrolimus increases the melanogenesis
and migration of melanocytes in vitro. Korean J Physiol Pharmacol. 2017
May;21(3):287-292. doi: 10.4196/kjpp.2017.21.3.287. Epub 2017 Apr 21. PubMed
PMID: 28461770; PubMed Central PMCID: PMC5409113.
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6: Malachowski SJ, Creasey M, Kinkley N, Heaphy MR Jr. Annular Lichenoid
Dermatitis of Youth: A Chronic Case Managed Using Pimecrolimus. Pediatr Dermatol.
2016 Nov;33(6):e360-e361. doi: 10.1111/pde.12987. Epub 2016 Sep 22. PubMed PMID:
27653808.
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7: Hussner J, Sünwoldt J, Seibert I, Gliesche DG, Zu Schwabedissen HE.
Pimecrolimus increases the expression of interferon-inducible genes that modulate
human coronary artery cells proliferation. Eur J Pharmacol. 2016 Aug
5;784:137-46. doi: 10.1016/j.ejphar.2016.05.020. Epub 2016 May 19. PubMed PMID:
27212382.
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8: Poddighe D, Brazzelli V, Licari A, Marseglia GL. Acute Pustular Dermatosis,
Following Topical Treatment With Pimecrolimus, in a Child Affected With Atopic
and Contact Hand Dermatitis. J Pediatr Pharmacol Ther. 2016 Jan-Feb;21(1):81-4.
doi: 10.5863/1551-6776-21.1.81. PubMed PMID: 26997932; PubMed Central PMCID:
PMC4778701.
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9: Yingfang F, Zhuang B, Wang C, Xu X, Xu W, Lv Z. Pimecrolimus micelle exhibits
excellent therapeutic effect for Keratoconjunctivitis Sicca. Colloids Surf B
Biointerfaces. 2016 Apr 1;140:1-10. doi: 10.1016/j.colsurfb.2015.11.059. Epub
2015 Dec 19. PubMed PMID: 26731192.

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10: Schmutz JL. [No increased risk of cancer under pimecrolimus]. Ann Dermatol
Venereol. 2016 Jan;143(1):98-9. doi: 10.1016/j.annder.2015.11.003. Epub 2015 Dec
18. French. PubMed PMID: 26708204.

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