Pimecrolimus
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MedKoo CAT#: 315295

CAS#: 137071-32-0

Description: 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.


Chemical Structure

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Pimecrolimus
CAS# 137071-32-0

Theoretical Analysis

MedKoo Cat#: 315295
Name: Pimecrolimus
CAS#: 137071-32-0
Chemical Formula: C43H68ClNO11
Exact Mass: 809.45
Molecular Weight: 810.463
Elemental Analysis: C, 63.72; H, 8.46; Cl, 4.37; N, 1.73; O, 21.72

Price and Availability

Size Price Availability Quantity
100mg USD 350 2 Weeks
200mg USD 550 2 Weeks
500mg USD 950 2 Weeks
1g USD 1650 2 Weeks
2g USD 2950 2 Weeks
Bulk inquiry

Synonym: ASM-981; ASM981; ASM 981; SDZ ASM 981; SDZ-ASM 981; SDZ-ASM-981; Pimecrolimus; Pimecrolimusum; 33-epi-Chloro-33-desoxyascomycin; Brand name: Aregen; Rizan; Elidel.

IUPAC/Chemical Name: (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.

InChi Key: KASDHRXLYQOAKZ-XDSKOBMDSA-N

InChi Code: 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

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Pimecrolimus (SDZ-ASM 981) is a potent, nonsteroid and orally active calcineurin inhibitor with a Ki of 117 nM.
In vitro activity: 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-gamma] 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)-alpha promoter in the murine mast-cell line CPII. Reference: Br J Dermatol. 1999 Aug;141(2):264-73. https://pubmed.ncbi.nlm.nih.gov/10468798/
In vivo activity: 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. SDZ ASM 981 potently inhibited allergic contact dermatitis in mice and rats when given systemically, and oral treatment was more effective than cyclosporin A in rats. Furthermore, SDZ ASM 981 has a low potential for affecting systemic immune responses, as demonstrated in rat models of localized graft vs. host reaction and allogeneic kidney transplantation. Reference: Br J Dermatol. 1997 Oct;137(4):568-76. https://pubmed.ncbi.nlm.nih.gov/9390333/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 24.68
DMSO 50.7 62.52
Ethanol 60.0 74.03
Ethanol:PBS (pH 7.2) (1:3) 0.3 0.31

Preparing Stock Solutions

The following data is based on the product molecular weight 810.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. PMID: 28461770; PMCID: PMC5409113. 2. Grassberger M, Baumruker T, Enz A, Hiestand P, Hultsch T, Kalthoff F, Schuler W, Schulz M, Werner FJ, Winiski A, Wolff B, Zenke G. A novel anti-inflammatory drug, SDZ ASM 981, for the treatment of skin diseases: in vitro pharmacology. Br J Dermatol. 1999 Aug;141(2):264-73. doi: 10.1046/j.1365-2133.1999.02974.x. PMID: 10468798. 3. Shin N, Jung N, Lee SE, Kong D, Kim NG, Kook MG, Park H, Choi SW, Lee S, Kang KS. Pimecrolimus interferes the therapeutic efficacy of human mesenchymal stem cells in atopic dermatitis by regulating NFAT-COX2 signaling. Stem Cell Res Ther. 2021 Aug 28;12(1):482. doi: 10.1186/s13287-021-02547-8. PMID: 34454603; PMCID: PMC8399851. 4. Meingassner JG, Grassberger M, Fahrngruber H, Moore HD, Schuurman H, Stütz A. A novel anti-inflammatory drug, SDZ ASM 981, for the topical and oral treatment of skin diseases: in vivo pharmacology. Br J Dermatol. 1997 Oct;137(4):568-76. doi: 10.1111/j.1365-2133.1997.tb03788.x. PMID: 9390333.
In vitro protocol: 1. 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. PMID: 28461770; PMCID: PMC5409113. 2. Grassberger M, Baumruker T, Enz A, Hiestand P, Hultsch T, Kalthoff F, Schuler W, Schulz M, Werner FJ, Winiski A, Wolff B, Zenke G. A novel anti-inflammatory drug, SDZ ASM 981, for the treatment of skin diseases: in vitro pharmacology. Br J Dermatol. 1999 Aug;141(2):264-73. doi: 10.1046/j.1365-2133.1999.02974.x. PMID: 10468798.
In vivo protocol: 1. Shin N, Jung N, Lee SE, Kong D, Kim NG, Kook MG, Park H, Choi SW, Lee S, Kang KS. Pimecrolimus interferes the therapeutic efficacy of human mesenchymal stem cells in atopic dermatitis by regulating NFAT-COX2 signaling. Stem Cell Res Ther. 2021 Aug 28;12(1):482. doi: 10.1186/s13287-021-02547-8. PMID: 34454603; PMCID: PMC8399851. 2. Meingassner JG, Grassberger M, Fahrngruber H, Moore HD, Schuurman H, Stütz A. A novel anti-inflammatory drug, SDZ ASM 981, for the topical and oral treatment of skin diseases: in vivo pharmacology. Br J Dermatol. 1997 Oct;137(4):568-76. doi: 10.1111/j.1365-2133.1997.tb03788.x. PMID: 9390333.

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