WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H300152
CAS#: 59865-13-3
Description: Cyclosporine A, also known as cyclosporine, is a natural cyclic polypeptide immunosuppressant isolated from the fungus Beauveria nivea. The exact mechanism of action of cyclosporine is not known but may involve binding to the cellular protein cytophilin, resulting in inhibition of the enzyme calcineurin. This agent appears to specifically and reversibly inhibit immunocompetent lymphocytes in the G0-or G1-phase of the cell cycle. T-lymphocytes are preferentially inhibited with T-helper cells as the primary target. Cyclosporine also inhibits lymphokine production and release.
Hodoodo Cat#: H300152
Name: Cyclosporine A
CAS#: 59865-13-3
Chemical Formula: C62H111N11O12
Exact Mass: 1,201.84
Molecular Weight: 1,202.610
Elemental Analysis: C, 61.92; H, 9.30; N, 12.81; O, 15.96
Synonym: Cyclosporine; Ciclosporin; cyclosporin; cyclosporin A.
IUPAC/Chemical Name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
InChi Key: PMATZTZNYRCHOR-CGLBZJNRSA-N
InChi Code: InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1
SMILES Code: CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
Appearance: white 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, not in water
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:
| Biological target: | Cyclosporin A is an immunosuppressant which binds to cyclophilin and inhibits phosphatase activity of calcineurin with an IC50 of 5 nM. |
| In vitro activity: | In vitro studies indicated that Cyclosporin A (CsA) inhibited partial OSCC (oral squamous cell carcinoma) growth by inducing cell cycle arrest, apoptosis, and the migration and invasion of OSCC cells. It was also demonstrated that CsA could inhibit the expression of NFATc1 and its downstream genes COX-2, c-Myc, MMP-9, and MMP-2 in OSCC cells. These data demonstrated that CsA can inhibit the progression of OSCC cells as well as mediate the signal molecules of NFATc1 signaling pathway, which has a strong relationship with cancer development. Reference: Anticancer Agents Med Chem. 2019;19(2):248-255. https://pubmed.ncbi.nlm.nih.gov/30378503/ |
| In vivo activity: | Cyclosporine A (Cyp A) was evaluated for its site-specificity in the treatment of TNBS induced colitis. The appearance of the drug in systemic circulation at approximately 5 hours in New Zealand strain of rabbits confirms drug delivery at distal parts of intestine. Significant reduced levels of TNF-α, IL-6 and IL-10 in drug treated animals signifies inhibition of inflammatory reactions at the TNBS treated site. Simultaneously, the change in body weight of the same group of animals was observed for 15 days. Results showed a marginal recovery of body weight in Cyp A treated TNBS induced colitis animals. In conclusion, all in vivo results confirm the successful site specific delivery and anti-inflammatory efficacy of developed formulation of Cyp A in TNBS induced colitis in New Zealand rabbits. Reference: Drug Dev Ind Pharm. 2020 Oct;46(10):1726-1733. https://www.tandfonline.com/doi/abs/10.1080/03639045.2020.1820041?journalCode=iddi20 |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 62.0 | 51.60 |
The following data is based on the product molecular weight 1,202.61 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.
| 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. Gao L, Dong J, Zhang N, Le Z, Ren W, Li S, Li F, Song J, Wang Q, Dou Z, Park SY, Zhi K. Cyclosporine A Suppresses the Malignant Progression of Oral Squamous Cell Carcinoma in vitro. Anticancer Agents Med Chem. 2019;19(2):248-255. doi: 10.2174/1871520618666181029170605. PMID: 30378503. 2. Fellman CL, Stokes JV, Archer TM, Pinchuk LM, Lunsford KV, Mackin AJ. Cyclosporine A affects the in vitro expression of T cell activation-related molecules and cytokines in dogs. Vet Immunol Immunopathol. 2011 Apr 15;140(3-4):175-80. doi: 10.1016/j.vetimm.2010.11.005. Epub 2010 Dec 4. PMID: 21227512. 3. Hajkova M, Jaburek F, Porubska B, Bohacova P, Holan V, Krulova M. Cyclosporine A promotes the therapeutic effect of mesenchymal stem cells on transplantation reaction. Clin Sci (Lond). 2019 Nov 15;133(21):2143-2157. doi: 10.1042/CS20190294. PMID: 31654074. 4. Sharma S, Sinha VR. In vitro and in vivo amelioration of colitis using targeted delivery system of cyclosporine a in New Zealand rabbits. Drug Dev Ind Pharm. 2020 Oct;46(10):1726-1733. doi: 10.1080/03639045.2020.1820041. Epub 2020 Sep 21. PMID: 32892648. |
| In vitro protocol: | 1. Gao L, Dong J, Zhang N, Le Z, Ren W, Li S, Li F, Song J, Wang Q, Dou Z, Park SY, Zhi K. Cyclosporine A Suppresses the Malignant Progression of Oral Squamous Cell Carcinoma in vitro. Anticancer Agents Med Chem. 2019;19(2):248-255. doi: 10.2174/1871520618666181029170605. PMID: 30378503. 2. Fellman CL, Stokes JV, Archer TM, Pinchuk LM, Lunsford KV, Mackin AJ. Cyclosporine A affects the in vitro expression of T cell activation-related molecules and cytokines in dogs. Vet Immunol Immunopathol. 2011 Apr 15;140(3-4):175-80. doi: 10.1016/j.vetimm.2010.11.005. Epub 2010 Dec 4. PMID: 21227512. |
| In vivo protocol: | 1. Hajkova M, Jaburek F, Porubska B, Bohacova P, Holan V, Krulova M. Cyclosporine A promotes the therapeutic effect of mesenchymal stem cells on transplantation reaction. Clin Sci (Lond). 2019 Nov 15;133(21):2143-2157. doi: 10.1042/CS20190294. PMID: 31654074. 2. Sharma S, Sinha VR. In vitro and in vivo amelioration of colitis using targeted delivery system of cyclosporine a in New Zealand rabbits. Drug Dev Ind Pharm. 2020 Oct;46(10):1726-1733. doi: 10.1080/03639045.2020.1820041. Epub 2020 Sep 21. PMID: 32892648. |
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2: Yamaji K. [Treatment of rheumatic diseases: current status and future prospective. Topics: II. Immunosuppressant/antirheumatic drugs; 7. Cyclosporine]. Nihon Naika Gakkai Zasshi. 2011 Oct 10;100(10):2942-7. Review. Japanese. PubMed PMID: 22175135.
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7: Sansone F, Rinaldi M. Cyclosporine monotherapy in cardiac transplantation: review of the literature. Transplant Rev (Orlando). 2011 Oct;25(4):131-5. Epub 2011 Apr 21. Review. PubMed PMID: 21514135.
8: Fabro M, Szabo H, Terrosu G, Avellini C, Tabuso M, Fiorino G, Sorrentino D. Acute severe colitis: infliximab and/or cyclosporine? Curr Drug Targets. 2011 Sep;12(10):1448-53. Review. PubMed PMID: 21466485.
9: Burger DC, Travis S. Colon salvage therapy for acute severe colitis: cyclosporine or infliximab? Curr Opin Gastroenterol. 2011 Jul;27(4):358-62. Review. PubMed PMID: 21423006.
10: Reese D, Henning JS, Rockers K, Ladd D, Gilson R. Cyclosporine for SJS/TEN: a case series and review of the literature. Cutis. 2011 Jan;87(1):24-9. Review. PubMed PMID: 21323097.
