Cyclosporine

Ciclosporin
Clinical data


Pronunciation	/ˌsaɪkləˈspɔːrɪn/
Trade names	Neoral, Sandimmune, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601207
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	By mouth, IV, eye drops
Drug class	immunosuppressant calcineurin inhibitor eye medication
ATC code	L04AD01 (WHO) S01XA18 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Variable
Metabolism	liver CYP3A4
Biological half-life	Variable (about 24 hours)
Excretion	biliary
Identifiers
IUPAC name (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
Synonyms	cyclosporine, cyclosporin, ciclosporin A, cyclosporine A, cyclosporin A (CsA)
CAS Number	59865-13-3^Y
PubChem (CID)	5284373
IUPHAR/BPS	1024
DrugBank	DB00091^N
ChemSpider	4447449^Y
UNII	83HN0GTJ6D^Y
KEGG	D00184^Y
ChEMBL	CHEMBL160^Y
ECHA InfoCard	100.119.569
Chemical and physical data
Formula	C₆₂H₁₁₁N₁₁O₁₂
Molar mass	1202.61 g/mol
3D model (Jmol)	Interactive image
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
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^Y Key:PMATZTZNYRCHOR-CGLBZJNRSA-N^Y
^NY (what is this?)

Ciclosporin
Identifiers
Symbol	N/A
OPM superfamily	174
OPM protein	1cwa

Ciclosporin, also spelled cyclosporine and cyclosporin, is an immunosuppressant medication and natural product. It is used by mouth and injection into a vein for rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, and in organ transplants to prevent rejection. It is also used as eye drops for (dry eyes).

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

Ciclosporin is believed to work by decreasing the function of lymphocytes. It does this by forming a complex with cyclophilin to block the phosphatase activity of calcineurin that in turn decreases the production of inflammatory cytokines by T‐lymphocytes.

Ciclosporin was isolated in 1971 from the fungus Tolypocladium inflatum and came into medical use in 1983. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 106.50 USD a month. In the United Kingdom it costs the NHS about 121.25 pounds per month. The wholesale price in the United States is about 172.95 USD per month.

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