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Ciclosporin

Not to be confused with cyclobenzaprine or cephalosporin.

Ciclosporin
Clinical data
Pronunciation/ˌsaɪkləˈspɔːrɪn/[1]
Trade namesSandimmune, others
Other namescyclosporin, ciclosporin A,[2] cyclosporine A, cyclosporin A (CsA), cyclosporine (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa601207
License data
Pregnancy
category
  • AU: C
Routes of
administration		Oral, intravenous (IV), eye drops
Drug classCalcineurin inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityvariable
MetabolismLiver CYP3A4
Elimination half-lifevariable (about 24 hours)
ExcretionBile duct
Identifiers
  • (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-Ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexen-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-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.119.569 Edit this at Wikidata
Chemical and physical data
FormulaC62H111N11O12
Molar mass1202.635 g·mol−1
3D model (JSmol)
  • 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
  • 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 checkY
  • Key:PMATZTZNYRCHOR-CGLBZJNRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ciclosporin, also spelled cyclosporine and cyclosporin, is a calcineurin inhibitor, used as an immunosuppressant medication. It is taken orally or intravenously for rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, eczema, and in organ transplants to prevent rejection.[14][15] It is also used as eye drops for keratoconjunctivitis sicca (dry eyes).[16]

Common side effects include high blood pressure, headache, kidney problems, increased hair growth, and vomiting.[15] Other severe side effects include an increased risk of infection, liver problems, and an increased risk of lymphoma.[15] Blood levels of the medication should be checked to decrease the risk of side effects.[15] Use during pregnancy may result in preterm birth; however, ciclosporin does not appear to cause birth defects.[17]

Ciclosporin is believed to work by decreasing the function of lymphocytes.[15] It does this by forming a complex with cyclophilin to block the phosphatase activity of calcineurin, which in turn decreases the production of inflammatory cytokines by T-lymphocytes.[18]

Ciclosporin was isolated in 1971 from the fungus Tolypocladium inflatum and came into medical use in 1983.[19] It is on the World Health Organization's List of Essential Medicines.[20][21] In 2022, it was the 185th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[22][23] It is available as a generic medication.[24]

  1. ^ "cyclosporin". Dictionary.com Unabridged. Random House. n.d. Archived from the original on 18 November 2010. Retrieved 13 July 2011.
  2. ^ Laupacis A, Keown PA, Ulan RA, McKenzie N, Stiller CR (May 1982). "Cyclosporin A: a powerful immunosuppressant". Canadian Medical Association Journal. 126 (9): 1041–6. PMC 1863293. PMID 7074504.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Regulatory Decision Summary for Restasis Multidose". Drug and Health Product Register. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  5. ^ "Regulatory Decision Summary for Verkazia". Drug and Health Product Register. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  6. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  7. ^ Cite error: The named reference Neoral FDA label was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Sandimmune FDA label was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Restasis FDA label was invoked but never defined (see the help page).
  10. ^ "Vevye- cyclosporine ophthalmic solution solution/ drops". DailyMed. 26 May 2023. Archived from the original on 29 August 2023. Retrieved 29 August 2023.
  11. ^ "Ikervis". European Medicines Agency. 17 September 2018. Archived from the original on 13 August 2022. Retrieved 27 February 2023.
  12. ^ Cite error: The named reference Vevizye EPAR was invoked but never defined (see the help page).
  13. ^ "Vevizye PI". Union Register of medicinal products. 23 September 2024. Retrieved 27 September 2024.
  14. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 221. hdl:10665/44053. ISBN 9789241547659.
  15. ^ a b c d e "Cyclosporine". The American Society of Health-System Pharmacists. Archived from the original on 17 October 2016. Retrieved 8 December 2016.
  16. ^ "Cyclosporine eent". The American Society of Health-System Pharmacists. Archived from the original on 13 January 2016. Retrieved 8 December 2016.
  17. ^ "Cyclosporine Use During Pregnancy". Drugs.com. Archived from the original on 14 September 2017. Retrieved 20 December 2016.
  18. ^ Cite error: The named reference Matsuda_2000 was invoked but never defined (see the help page).
  19. ^ Watts R, Clunie G, Hall F, Marshall T (2009). Rheumatology. Oxford University Press. p. 558. ISBN 978-0-19-922999-4. Archived from the original on 5 November 2017.
  20. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  21. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  22. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  23. ^ "Cyclosporine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  24. ^ "FDA Approves First Generic of Restasis". U.S. Food and Drug Administration (FDA) (Press release). 2 February 2022. Archived from the original on 2 February 2022. Retrieved 3 February 2022.
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