Cyclosporine

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Cyclosporine.png
Ciclosporin chemical structure


Ciclosporin

[R-[R*,R*-(E)]]-cyclic(L-alanyl-D-alanyl-
N-methyl-L-leucyl-N-methyl-L-leucyl-
N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-
L-2-amino-6-octenoyl-L-α-amino-butyryl-
N-methylglycyl-N-methyl-L-leucyl-L-valyl-
N-methyl-L-leucyl)
CAS number
59865-13-3
ATC code
L04AA01
Chemical formula C62H111N11O12
Molecular weight 1202.61
Bioavailability variable
Metabolism hepatic
Elimination half-life variable
Excretion biliary
Pregnancy category C (USA)
C (Aus)
Legal status N/A
Routes of administration  ?

Cyclosporine, Ciclosporin (INN), or cyclosporin (former BAN), is an immunosuppressant drug. It is used post-allogenic organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It has been studied in transplants of skin, heart, kidney, lung, pancreas, bone marrow and small intestine. Cyclosporine is a cyclic nonribosomal peptide of 11 amino acids produced by the fungus Hypocladium inflatum gams, initially isolated from a Norwegian soil sample.Template:Ref

The drug is sold by Novartis under the brand names Sandimmune and Neoral. Generic cyclosporine drugs have been produced by companies such as Sangstat, Abbott Laboratories and Gengraf. Since 2002 a topical emulsion of cyclosporine for treating keratoconjunctivitis sicca has been marketed under the trade name Restasis. Annual sales of cyclosporine are around $1 billion.

Cyclosporine was discovered in 1970 in a Norwegian soil fungus by Jean F. Borel at Sandoz laboratories and it was approved for use in 1983.

Although the international noproprietary name is now ciclosporin, it is still referred to as cyclosporine in most scientific journals.

Contents

Uses

Apart from in transplant medicine, cyclosporine is also used in psoriasis and infrequently in rheumatoid arthritis and related diseases, although it is only used in severe cases. It has been investigated for use in many other autoimmune disorders. It is often taken in conjunction with corticosteroids. More recently, cyclosporine has begun to be used to help treat patients suffering from ulcerative colitis with positive results.

Mode of action

Cyclosporine is thought to bind to the cytosolic protein cyclophilin (immunophilin) of immunocompetent lymphocytes, especially T-lymphocytes. This complex of cyclosporin and cyclophylin inhibits calcineurin, which under normal circumstances is responsible for activating the transcription of interleukin-2. It also inhibits lymphokine production and interleukin release and therefore leads to a reduced function of effector T-cells. It does not affect cytostatic activity.

Side-effects and interactions

Treatment has a number of potentially serious side effects and has adverse interactions with a wide variety of other drugs and other materials including grapefruit, although there have been studies to improve the blood level of cyclosporine with grapefruit juice. Side effects can include gum hyperplasia, convulsions, peptic ulcers, pancreatitis, fever, vomiting, diarrhea, confusion, breathing difficulties, numbness and tingling, pruritus, high blood pressure, kidney and liver disfunction, potassium retention and possibly hyperkalemia, hepatotoxicity, nephrotoxicity, and obviously an increased vulnerability to opportunistic fungal and viral infections.

See also

External link

  • PDF at Novartis (http://www.pharma.us.novartis.com/product/pi/pdf/sandimmune.pdf)

Notes

  1. Template:Note Pritchard, David I. 2005. "Sourcing a chemical succession for cyclosporin from parasites and human pathogens". Drug Discovery Today 10[10]:688-691. An alternative species name, Tolypocladium inflatum, appears in a 2001 online publication by Harriet Upton entitled "Origin of drugs in current use: the cyclosporin story (http://www.world-of-fungi.org/Mostly_Medical/Harriet_Upton/Harriet_Upton.htm)" (retrieved June 19, 2005).de:Ciclosporin
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