Cyclosporine A

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MedKoo CAT#: 300152

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.

Chemical Structure

Cyclosporine A
CAS# 59865-13-3

Theoretical Analysis

MedKoo Cat#: 300152
Name: Cyclosporine A
CAS#: 59865-13-3
Chemical Formula: C62H111N11O12
Exact Mass: 1201.84137
Molecular Weight: 1202.61124
Elemental Analysis: C, 61.92; H, 9.30; N, 12.81; O, 15.96

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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 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1202.61124 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

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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.