MedKoo Cat#: 300152 | Name: Cyclosporine A
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Description:

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

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.

Chemical Structure

Cyclosporine A
Cyclosporine A
CAS#59865-13-3

Theoretical Analysis

MedKoo Cat#: 300152

Name: Cyclosporine A

CAS#: 59865-13-3

Chemical Formula: C62H111N11O12

Exact Mass: 1201.8414

Molecular Weight: 1202.61

Elemental Analysis: C, 61.92; H, 9.30; N, 12.81; O, 15.96

Price and Availability

Size Price Availability Quantity
500mg USD 150.00 Ready to ship
1g USD 210.00 Ready to ship
2g USD 350.00 Ready to ship
5g USD 550.00 Ready to ship
10g USD 950.00 Ready to ship
20g USD 1,650.00 Ready to ship
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Related CAS #
No Data
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 mg/mL mM
Solubility
DMSO 62.0 51.60
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 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.

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. 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.
1: Colombo D, Ammirati E. Cyclosporine in transplantation - a history of converging timelines. J Biol Regul Homeost Agents. 2011 Oct-Dec;25(4):493-504. Review. PubMed PMID: 22217983. 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. 3: Seo SR, Lee SJ, Park DJ, Kim TJ, Park YW, Lee SS. Successful treatment using cyclosporine in a patient with rhupus complicated by aplastic anemia: a case report and review of the literature. Clin Exp Rheumatol. 2011 Jul-Aug;29(4):708-11. Epub 2011 Sep 1. Review. PubMed PMID: 21813067. 4: Xiao Z, Li C, Shan J, Luo L, Feng L, Lu J, Li S, Long D, Li Y. Mechanisms of renal cell apoptosis induced by cyclosporine A: a systematic review of in vitro studies. Am J Nephrol. 2011;33(6):558-66. Epub 2011 May 26. Review. PubMed PMID: 21613783. 5: Osman MM, Lulic D, Glover L, Stahl CE, Lau T, van Loveren H, Borlongan CV. Cyclosporine-A as a neuroprotective agent against stroke: its translation from laboratory research to clinical application. Neuropeptides. 2011 Dec;45(6):359-68. Epub 2011 May 17. Review. PubMed PMID: 21592568. 6: Liang LY, Zhang FK. [Latest advance of clinical significances of pharmacokinetic and pharmacodynamic of cyclosporine A]. Zhonghua Xue Ye Xue Za Zhi. 2011 Apr;32(4):284-6. Review. Chinese. PubMed PMID: 21569718. 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.