Cyclosporine A

For research use only. Not for therapeutic Use.

  • CAT Number: A000634
  • CAS Number: 59865-13-3
  • Molecular Formula: C₆₂H₁₁₁N₁₁O₁₂
  • Molecular Weight: 1202.60
  • Purity: ≥95%
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Cyclosporine A(Cat No.:A000634)is a potent immunosuppressive agent widely used to prevent organ transplant rejection and treat autoimmune diseases. It functions by inhibiting calcineurin, a key enzyme in the activation of T-cells, thereby suppressing the immune response. Cyclosporine A specifically binds to cyclophilin, forming a complex that blocks the transcription of interleukin-2 and other cytokines. Its efficacy in controlling immune reactions has made it a cornerstone in transplant medicine, as well as in the treatment of conditions like rheumatoid arthritis and psoriasis. Cyclosporine A’s targeted action minimizes overactive immune responses while preserving general immunity.


Catalog Number A000634
CAS Number 59865-13-3
Synonyms

Ciclosporin; Cyclosporine; Neoral; Ciclosporine; Cyclosporin

Molecular Formula C₆₂H₁₁₁N₁₁O₁₂
Purity ≥95%
Storage -20°C
IUPAC Name (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
InChI 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
InChIKey PMATZTZNYRCHOR-CGLBZJNRSA-N
SMILES 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
Reference

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Stanković A, Kostić M. Effect of Age and Allele Variants of CYP3A5, CYP3A4, and
POR Genes on the Pharmacokinetics of Cyclosporin A in Pediatric Renal Transplant
Recipients From Serbia. Ther Drug Monit. 2017 Dec;39(6):589-595. doi:
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MS, Rezaei-Tavirani M. Er:YAG Laser and Cyclosporin A Effect on Cell Cycle
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activation of group 2 innate lymphoid cells in papain-induced lung inflammation.
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5: Retraction: Inhibition of Arachidonic Acid Release by Cytosolic Phospholipase
A2 Is Involved in the Antiapoptotic Effect of FK506 and Cyclosporin A on
Astrocytes Exposed to Simulated Ischemia In Vitro. J Pharmacol Sci. 2017 Oct
19;102(1). doi: 10.1254/jphs.FP0060605. PubMed PMID: 29083842.

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R, Matsuda T. Anti-IL-17A blocking antibody reduces cyclosporin A-induced relapse
in experimental autoimmune encephalomyelitis mice. Biochem Biophys Rep. 2016 Aug
26;8:139-145. doi: 10.1016/j.bbrep.2016.08.021. eCollection 2016 Dec. PubMed
PMID: 28955949; PubMed Central PMCID: PMC5613930.
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7: Fu J, Becker C, Cao L, Capparelli M, Denay R, Fujimoto R, Gai Y, Gao Z, Guenat
C, Karur S, Kim H, Li W, Li X, Li W, Lochmann T, Lu A, Lu P, Luneau A, Meier N,
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F, Simmons RL, Sun F, Sweeney ZK, Tjandra M, Wang M, Wang R, Weiss AH, Wenger N,
Wu Q, Xiong X, Xu S, Xu W, Yifru A, Zhao J, Zhou J, Zürcher C, Gallou F.
Development of a cyclosporin A derivative with excellent anti-hepatitis C virus
potency. Bioorg Med Chem. 2017 Sep 7. pii: S0968-0896(17)31223-3. doi:
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8: Kasitanon N, Boripatkosol P, Louthrenoo W. Response to combination of
mycophenolate mofetil, cyclosporin A and corticosteroid treatment in lupus
nephritis patients with persistent proteinuria. Int J Rheum Dis. 2017 Sep 13.
doi: 10.1111/1756-185X.13152. [Epub ahead of print] PubMed PMID: 28901731.
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9: Witek J, Keller BG, Blatter M, Meissner A, Wagner T, Riniker S. Correction to
Kinetic Models of Cyclosporin A in Polar and Apolar Environments Reveal Multiple
Congruent Conformational States. J Chem Inf Model. 2017 Sep 25;57(9):2393. doi:
10.1021/acs.jcim.7b00502. Epub 2017 Sep 12. PubMed PMID: 28898064.
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Sugai DY, Schalock P, Kroshinsky D. Successful Use of Cyclosporin A for
Stevens-Johnson Syndrome and Toxic Epidermal Necrolysis in Three Children.
Pediatr Dermatol. 2017 Sep;34(5):540-546. doi: 10.1111/pde.13236. PubMed PMID:
28884910.

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