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Ciclosporin Identifiers Symbol N/A OPM superfamily 94 OPM protein 1cwa
Ciclosporin, also spelled cyclosporine and cyclosporin, is an immunosuppressant medication and natural product.
Common side effects include high blood pressure, headache, kidney problems, increased hair growth, and vomiting.
Ciclosporin is believed to work by decreasing the function of lymphocytes.
Ciclosporin was isolated in 1971 from the fungus Tolypocladium inflatum and came into medical use in 1983.
Contents
1 Medical uses
2 Side effects
3 Pharmacology
3.1 Mechanism of action
3.2 Pharmacokinetics
4 Biosynthesis
5 History
6 Society and culture
6.1 Name
6.2 Available forms
7 Research
7.1 Neuroprotection
7.2 Cardiac disease
8 Veterinary use
9 See also
10 References
11 External links
Medical uses
Ciclosporin is approved by the FDA to treat and prevent graft-versus-host disease in bone marrow transplantation and to prevent rejection of kidney, heart, and liver transplants.
In addition to these indications, ciclosporin is also used in severe atopic dermatitis, Kimura disease, pyoderma gangrenosum, chronic hives, acute systemic mastocytosis, and posterior or intermediate uveitis with noninfective cause.
Ciclosporin has also been used in people with acute severe ulcerative colitis and hives that do not respond to treatment with steroids.
Side effects
Side effects of ciclosporin can include gum enlargement, increased hair growth, convulsions, peptic ulcers, pancreatitis, fever, vomiting, diarrhea, confusion, increased cholesterol, trouble breathing, numbness and tingling (particularly of the lips), itchiness, high blood pressure, potassium retention (possibly leading to hyperkalemia ), kidney and liver dysfunction,
Ciclosporin use after a kidney transplantation is associated with increased levels of uric acid in the blood and, in some cases, gout. which leads to uric acid retention. Use of azathioprine as an alternative has shown to reduce the incidence of gouty arthritis.
Ciclosporin is listed as an IARC Group 1 carcinogen (i.e. there is sufficient evidence of carcinogenicity in humans),
Pharmacology
Mechanism of action
Ciclosporin’s main effect is to lower the activity of T-cells ; it does so by calcineurin–phosphatase pathway and preventing the mitochondrial permeability transition pore from opening. Ciclosporin binds to the cytosolic protein cyclophilin (immunophilin) of lymphocytes, especially of T cells. This cyclosporin—cyclophilin complex inhibits calcineurin, which is normally responsible for activating the transcription of interleukin 2. In T-cells, activation of the T-cell receptor normally increases intracellular calcium, which acts via calmodulin to activate calcineurin. Calcineurin then dephosphorylates the transcription factor NF-AT (nuclear factor of activated T-cells), which moves to the T-cell nucleus and increases the transcription of genes for IL-2 and related cytokines. it does not affect cytostatic activity.
Ciclosporin also binds to the cyclophilin D protein that constitutes part of the mitochondrial permeability transition pore (MPTP).
Pharmacokinetics
Ciclosporin is a cyclic peptide of 11 amino acids ; it contains a single D -amino acid, which is rarely encountered in nature. Unlike most peptides, ciclosporin is not synthesized by ribosomes.
Ciclosporin is highly metabolized in humans and animals after ingestion. The metabolites, which include cyclosporin B, C, D, E, H, and L, Individual ciclosporin metabolites have been isolated and characterized but do not appear to be extensively studied.
Biosynthesis
Cyclosporin biosynthesis. Bmt = butenyl-methyl-threonine, Abu = L-alpha-aminobutyric acid, Sar = sarcosine
Cyclosporin is synthesized by a nonribosomal peptide synthetase, cyclosporin synthetase.
History
In 1970, new strains of fungi were isolated from soil samples taken from Norway and from Wisconsin in the US by employees of Sandoz (now Novartis ) in Basel, Switzerland. Both strains produced a family of natural products called cyclosporins. Two related components that had antifungal activity were isolated from extracts from these fungi. The Norwegian strain, Tolypocladium inflatum Gams, was later used for the large scale fermentation of ciclosporin.
The immunosuppressive effect of the natural product cyclosporin was discovered in December 1971 in a screening test on immune suppression designed and implemented by Hartmann F. Stähelin at Sandoz.
Society and culture
Name
The natural product was named cyclosporin by the German speaking scientists who first isolated it the “y” was replaced with “i” so that the INN for the medication is spelled ciclosporin.
Ciclosporin is the INN and British Approved Name (BAN), while cyclosporine is the United States Adopted Name (USAN) and cyclosporin is a former BAN.
Available forms
Ciclosporin exhibits very poor solubility in water, and, as a consequence, suspension and emulsion forms of the medication have been developed for oral administration and for injection. Ciclosporin was originally brought to market by Sandoz (now Novartis ), under the brand name Sandimmune, which is available as soft gelatin capsules, an oral solution, and a formulation for intravenous administration. These are all nonaqueous compositions. is available as a solution and as soft gelatin capsules. The Neoral compositions are designed to form microemulsions in contact with water.
Generic ciclosporin preparations have been marketed under various trade names, including Cicloral ( Sandoz/Hexal ), Gengraf ( Abbott ) and Deximune ( Dexcel Pharma ). Since 2002, a topical emulsion of ciclosporin for treating inflammation caused by keratoconjunctivitis sicca (dry eye syndrome) has been marketed under the trade name Restasis (0.05%). Ikervis is a similar formulation with a concentration of 0.1%.
Research
Neuroprotection
Ciclosporin is currently in a phase II/III (adaptive) clinical study in Europe to determine its ability to ameliorate neuronal cellular damage and reperfusion injury (phase III) in traumatic brain injury. This multi-center study is being organized by NeuroVive Pharma and the European Brain Injury Consortium using NeuroVive’s formulation of ciclosporin called NeuroSTAT (also known by its cardioprotection trade name of CicloMulsion ). This formulation uses a lipid emulsion base instead of cremophor and ethanol.
Ciclosporin has been investigated as a possible neuroprotective agent in conditions such as traumatic brain injury, and has been shown in animal experiments to reduce brain damage associated with injury.
Cardiac disease
Ciclosporin has been used experimentally to treat cardiac hypertrophy (an increase in cell volume).
Inappropriate opening of the mitochondrial permeability transition pore (MPTP) manifests in ischemia
CsA (cyclosporin A) has been shown to decrease cardiac hypertrophy by affecting cardiac myocytes in many ways. CsA binds to cyclophilin D to block the opening of MPTP, and thus decreases the release of protein cytochrome C, which can cause programmed cell death.
Veterinary use
The medication is approved in the United States for the treatment of atopic dermatitis in dogs.
It is sometimes prescribed for extreme cases of immune-mediated hemolytic anemia.
See also
Cremophor EL (additive in Sandimmune)
Castor oil (additive in Sandimmune)
Ethanol (additive in Sandimmune and Neoral)
Voclosporin, an analog of ciclosporin

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