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QuickView for Cyclosporine (compound)


PubChem
Name: Cyclosporine
PubChem Compound ID: 2909
Description: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).
Molecular formula: C62H111N11O12
Molecular weight: 1202.61 g/mol
Synonyms:
NINDS_000871; Spectrum3_001593; KBio2_005916; Spectrum4_001279; Spectrum_000300; DivK1c_000871; KBio2_000780; KBio2_003348; Spectrum2_001484; KBio3_002686.
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DrugBank
Identification
Name: Cyclosporine
Name (isomeric): DB00091
Drug Type: biotech
Description: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).
Synonyms:
Cyclosporin; Ciclosporin; Cyclosporin A
Brand: Neoral (Novartis), Restasis, Sandimmune (Novartis), Gengraf (Abbott labs), Sangcya, Restasis (Allergan Inc)
Category: Antifungal Agents, Immunomodulatory Agents, Enzyme Inhibitors, Antirheumatic Agents, Immunosuppressive Agents, Dermatologic Agents
CAS number: 59865-13-3
Pharmacology
Indication: For treatment of transplant rejection, rheumatoid arthritis, severe psoriasis
Pharmacology:
Used in immunosuppression for prophylactic treatment of organ transplants, cyclosporine exerts specific and reversible inhibition of immunocompetent lymphocytes in the G0-or G1-phase of the cell cycle. T-lymphocytes are preferentially inhibited. The T1-helper cell is the main target, although the T1-suppressor cell may also be suppressed. Sandimmun...
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Mechanism of Action:
Cyclosporine binds to cyclophilin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial...
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Absorption: The absorption of cyclosporine from the gastrointestinal tract is incomplete and variable. Compared to an intravenous infusion, the absolute bioavailability of the oral solution is approximately 30% based upon the results in 2 patients.
Protein binding: Approximately 90% is bound to proteins, primarily lipoproteins.
Biotransformation: Hepatic, extensively metabolized.
Route of elimination: Elimination is primarily biliary with only 6% of the dose excreted in the urine. Only 0.1% of the dose is excreted in the urine as unchanged drug.
Half Life: Biphasic and variable, approximately 7 hours (range 7 to 19 hours) in children and approximately 19 hours (range 10 to 27 hours) in adults.
Toxicity: The oral LD50 is 2329 mg/kg in mice, 1480 mg/kg in rats, and > 1000 mg/kg in rabbits. The I.V. LD50 is 148 mg/kg in mice, 104 mg/kg in rats, and 46 mg/kg in rabbits.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Red wine may reduce cyclosporine levels due to increased metabolism, therefore it appears prudent to avoid red wine (white wine does not appear to affect cyclosporine metabolism).
Avoid taking with grapefruit or grapefruit juice as grapefruit can significantly increase serum levels of this product.
Avoid salt substitutes containing potassium.
Take without regard to meals.
Drug interaction:
PyrazinamidePyrazinamide decreases the effect of cyclosporine
KetoprofenThe NSAID, ketoprofen, may increase the serum concentration of cyclosporine. Ketoprofen may also increase the nephrotoxicity of cyclosporine.
TalbutalThe sulfonamide decreases the effect of cyclosporine
RitonavirThe protease inhibitor, ritonavir, may increase the effect of cyclosporine.
QuinupristinSynercid increases the effect of cyclosporine
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