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MedKoo Cat#: 315295 | Name: Pimecrolimus
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Pimecrolimus
Pimecrolimus
CAS#137071-32-0

Theoretical Analysis

MedKoo Cat#: 315295

Name: Pimecrolimus

CAS#: 137071-32-0

Chemical Formula: C43H68ClNO11

Exact Mass: 809.4481

Molecular Weight: 810.46

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 350.00 2 Weeks
200mg USD 550.00 2 Weeks
500mg USD 950.00 2 Weeks
1g USD 1,650.00 2 Weeks
2g USD 2,950.00 2 Weeks
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Related CAS #
No Data
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
Product Data
Instruction
View handling instruction
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/
Solvent mg/mL mM comments
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
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
 1: Sidiropoulou P, Katsarou M, Sifaki M, Papasavva M, Drakoulis N. Topical calcineurin and mammalian target of rapamycin inhibitors in inflammatory dermatoses: Current challenges and nanotechnology‑based prospects (Review). Int J Mol Med. 2024 Oct;54(4):85. doi: 10.3892/ijmm.2024.5409. Epub 2024 Aug 12. PMID: 39129316; PMCID: PMC11335355. 2: Lax SJ, Van Vogt E, Candy B, Steele L, Reynolds C, Stuart B, Parker R, Axon E, Roberts A, Doyle M, Chu DK, Futamura M, Santer M, Williams HC, Cro S, Drucker AM, Boyle RJ. Topical anti-inflammatory treatments for eczema: network meta- analysis. Cochrane Database Syst Rev. 2024 Aug 6;8(8):CD015064. doi: 10.1002/14651858.CD015064.pub2. PMID: 39105474; PMCID: PMC11301992. 3: Liang KR, Lee C, Hilts A, Greenberg HL. Resolution of Discoid Lupus Alopecia With Systemic Hydroxychloroquine and Topical Pimecrolimus Combination Therapy. Cureus. 2024 Jun 28;16(6):e63419. doi: 10.7759/cureus.63419. PMID: 39077308; PMCID: PMC11284255. 4: Zacharopoulou A, Tsiogka A, Tsimpidakis A, Lamia A, Koumaki D, Gregoriou S. Tinea Incognito: Challenges in Diagnosis and Management. J Clin Med. 2024 May 31;13(11):3267. doi: 10.3390/jcm13113267. PMID: 38892976; PMCID: PMC11172699. 5: Kim EJ, Ershadi S, Barbieri J, Ho T. Medicaid coverage for nonsteroidal topical atopic dermatitis treatment is often restrictive and variable across the United States. Arch Dermatol Res. 2024 Jun 15;316(7):406. doi: 10.1007/s00403-024-03165-z. PMID: 38878103. 6: Kim SR, Lee JM, Kang HJ, Ryou J, Shim SM. Antiviral activity of pimecrolimus against dengue virus type 2 infection in vitro and in vivo. Sci Rep. 2024 Jun 10;14(1):13303. doi: 10.1038/s41598-024-61127-x. PMID: 38858399; PMCID: PMC11164929. 7: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Tacrolimus. 2024 May 15. PMID: 30000163. 8: Lamba P. Lichen Planus Treated with Individualized Homeopathic Medicine, A Case Report. Altern Ther Health Med. 2024 Apr;30(4):144-147. PMID: 38702160. 9: Xiang DH, Ji H, Cheng D, Semenov Y, Theodosakis N. Investigating price trends and cost-saving opportunities for prescription of topical calcineurin inhibitors using the Truven Marketscan Database. J Am Acad Dermatol. 2024 Aug;91(2):356-359. doi: 10.1016/j.jaad.2024.04.025. Epub 2024 Apr 19. PMID: 38642858. 10: Cheng SY, Wang ZW, Dai RP. Atopic Dermatitis Associated Retinal Detachment and Retinal Vasculitis: A Case Report. Chin Med Sci J. 2024 Mar;39(1):74-78. doi: 10.24920/004321. PMID: 38623049. 11: Roflumilast foam (Zoryve) for seborrheic dermatitis. Med Lett Drugs Ther. 2024 Apr 15;66(1700):57-59. doi: 10.58347/tml.2024.1700a. PMID: 38576147. 12: Hernandez TD, Aleman SJ, Bao-Loc-Trung M, Forte MV, Brandt W, Armstrong C, Howard J, Mosieri CN, Ahmadzadeh S, Varrassi G, Shekoohi S, Kaye AD. Advancing Treatment in Atopic Dermatitis: A Comprehensive Review of Clinical Efficacy, Safety, and Comparative Insights Into Corticosteroids, Calcineurin Inhibitors, and Phosphodiesterase-4 Inhibitors as Topical Therapies. Cureus. 2024 Mar 2;16(3):e55393. doi: 10.7759/cureus.55393. PMID: 38562326; PMCID: PMC10982833. 13: Lo A, Greenzaid JD, Gantz HY, Chodri K, Feldman SR. Clinical pharmacokinetics and pharmacodynamics of topical non-biological therapies for psoriasis patients. Expert Opin Drug Metab Toxicol. 2024 Apr;20(4):235-248. doi: 10.1080/17425255.2024.2337749. Epub 2024 Apr 2. PMID: 38553411. 14: Kocanci FG, Erol AYG, Yildiz F, Eciroglu H. Pimecrolimus protects neuron- like SH-SY5Y cells against anti-inflammatory and anti-oxidant effects of both microglial secretome and hydrogen peroxide. Scand J Immunol. 2024 Jan;99(1):e13328. doi: 10.1111/sji.13328. Epub 2023 Sep 11. PMID: 38441277. 15: Cheng SY, Wang ZW, Dai RP. Retinal Vasculitis as an Ocular Manifestation in Atopic Dermatitis-Associated Retinal Detachment: A Case Report. Chin Med Sci J. 2024 Feb 29. doi: 10.24920/004321. Epub ahead of print. PMID: 38419269. 16: Lupon E, Berkane Y, Bertheuil N, Cetrulo CL, Vaillant C, Chaput B, Camuzard O, Lellouch AG. Nonsurgical Treatment of Postburn Hypopigmentation: A Literature Review. J Burn Care Res. 2024 May 6;45(3):601-607. doi: 10.1093/jbcr/irae030. PMID: 38401148. 17: Luger T, Chu CY, Elgendy A, Ibrahim SBBK, Murashkin N, Ranjan S, Zhao Z. Pimecrolimus 1% cream for mild-to-moderate atopic dermatitis: a systematic review and meta-analysis with a focus on children and sensitive skin areas. Eur J Dermatol. 2023 Oct 1;33(5):474-486. doi: 10.1684/ejd.2023.4556. PMID: 38297923. 18: Ranpariya M, Zaino ML, McCampbell LE, Patel T, Feldman SR. Non-Systemic Medication for the Treatment of Prurigo Nodularis: A Systematic Review. J Cutan Med Surg. 2024 Mar-Apr;28(2):173-177. doi: 10.1177/12034754241227634. Epub 2024 Jan 30. PMID: 38291823. 19: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Pimecrolimus. 2024 Jan 15. PMID: 30000478. 20: Albagieh H, Alshagroud RS, Aladnan AM, Aldosari B, Alburaykan YB, Almashham LY, Alqasem AA, Alyahya AA, Aboheimed NI. Morphea Involving the Lips and Gingiva: A Rare Case Report. Cureus. 2023 Dec 27;15(12):e51202. doi: 10.7759/cureus.51202. PMID: 38155978; PMCID: PMC10754225.