Back Siklosporien Afrikaans سيكلوسبورين Arabic سیکلوسپورین AZB Ciklosporin BS Ciclosporina Catalan Ciclosporin Welsh Ciclosporin German Κυκλοσπορίνη Greek Ciclosporina Spanish Ziklosporina Basque

Ciclosporin

Not to be confused with cyclobenzaprine or cephalosporin.

Ciclosporin
Clinical data
Pronunciation/ˌsaɪkləˈspɔːrɪn/[1]
Trade namesNeoral, Sandimmune, Restasis, Gengraf, other
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		by mouth, 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.[12][13] It is also used as eye drops for keratoconjunctivitis sicca (dry eyes).[14]

Common side effects include high blood pressure, headache, kidney problems, increased hair growth, and vomiting.[13] Other severe side effects include an increased risk of infection, liver problems, and an increased risk of lymphoma.[13] Blood levels of the medication should be checked to decrease the risk of side effects.[13] Use during pregnancy may result in preterm birth; however, ciclosporin does not appear to cause birth defects.[15]

Ciclosporin is believed to work by decreasing the function of lymphocytes.[13] 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.[16]

Ciclosporin was isolated in 1971 from the fungus Tolypocladium inflatum and came into medical use in 1983.[17] It is on the World Health Organization's List of Essential Medicines.[18][19] In 2021, it was the 175th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[20][21] It is available as a generic medication.[22]

  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. ^ 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.
  13. ^ 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.
  14. ^ "Cyclosporine eent". The American Society of Health-System Pharmacists. Archived from the original on 13 January 2016. Retrieved 8 December 2016.
  15. ^ "Cyclosporine Use During Pregnancy". Drugs.com. Archived from the original on 14 September 2017. Retrieved 20 December 2016.
  16. ^ Cite error: The named reference Matsuda_2000 was invoked but never defined (see the help page).
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  21. ^ "Cyclosporine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  22. ^ "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.

Rich TVX News Network Site

Rich TVX News Network Info

© MMXXIII Rich X Search. We shall prevail. All rights reserved. Rich X Search