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QuickView for cyclosporin (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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NINDS_000871; Spectrum3_001593; KBio2_005916; Spectrum4_001279; Spectrum_000300; DivK1c_000871; KBio2_000780; KBio2_003348; Spectrum2_001484; KBio3_002686; KBio1_000871; KBioGR_001898; KBioSS_000780; SPBio_001467
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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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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. Sandimmune (cyclosporine) also inhibits lymphokine production and release including interleukin-2.
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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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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 immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
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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: |
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| Drug interaction: |
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Targets
Likely involved in the mobilization of calcium as a result of the TCR/CD3 complex interaction. Binds to cyclophilin B
| UniProt ID: | P49069 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | CAMLG | ||||||
| Actions: | binder | ||||||
| References: |
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Regulatory subunit of calcineurin, a calcium-dependent, calmodulin stimulated protein phosphatase. Confers calcium sensitivity
| UniProt ID: | Q96LZ3 | |||
|---|---|---|---|---|
| Gene: | PPP3R2 | |||
| Actions: | inhibitor | |||
| References: |
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PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides
| UniProt ID: | P62937 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | PPIA | ||||||
| Actions: | unknown | ||||||
| References: |
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Enzymes
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P24462 | ||
|---|---|---|---|
| Gene: | CYP3A7 | ||
| Actions: | substrate, inducer | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P20815 | ||
|---|---|---|---|
| Gene: | CYP3A5 | ||
| Actions: | substrate, inducer | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | |||
|---|---|---|---|---|
| Gene: | CYP3A4 | |||
| Actions: | substrate, inhibitor | |||
| References: |
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Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine
| UniProt ID: | P33261 | |
|---|---|---|
| Gene: | CYP2C19 | |
| Actions: | inhibitor | |
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)
| UniProt ID: | P10632 | |
|---|---|---|
| Gene: | CYP2C8 | |
| Actions: | inhibitor | |
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
| UniProt ID: | P11712 | |
|---|---|---|
| Gene: | CYP2C9 | |
| Actions: | inhibitor | |
| References: |
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Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
| UniProt ID: | P10635 | |
|---|---|---|
| Gene: | CYP2D6 | |
| Actions: | inhibitor | |
| References: |
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Transporters
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
| UniProt ID: | P08183 | |||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | ABCB1 | |||||||||||||||||||||||||||||||||||||||
| Actions: | substrate, inhibitor, inducer | |||||||||||||||||||||||||||||||||||||||
| References: |
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May act as an inducible transporter in the biliary and intestinal excretion of organic anions
| UniProt ID: | O15438 | |
|---|---|---|
| Gene: | ABCC3 | |
| Actions: | inhibitor | |
| References: |
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Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
| UniProt ID: | O95342 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | ABCB11 | ||||||
| Actions: | inhibitor | ||||||
| References: |
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May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics
| UniProt ID: | P33527 | ||
|---|---|---|---|
| Gene: | ABCC1 | ||
| Actions: | inhibitor | ||
| References: |
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Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)
| UniProt ID: | P46721 | |
|---|---|---|
| Gene: | SLCO1A2 | |
| Actions: | inhibitor | |
| References: |
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Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
| UniProt ID: | Q12908 | |
|---|---|---|
| Gene: | SLC10A2 | |
| Actions: | inhibitor | |
| References: |
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The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium
| UniProt ID: | Q14973 | |
|---|---|---|
| Gene: | SLC10A1 | |
| Actions: | inhibitor | |
| References: |
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| UniProt ID: | Q4U2R8 | |
|---|---|---|
| Gene: | SLC22A6 | |
| Actions: | inhibitor | |
| References: |
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ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion
| UniProt ID: | Q5T3U5 | |
|---|---|---|
| Gene: | ABCC10 | |
| Actions: | inhibitor | |
| References: |
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Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
| UniProt ID: | Q92887 | |||||
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| Gene: | ABCC2 | |||||
| Actions: | inhibitor | |||||
| References: |
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Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
| UniProt ID: | Q9UNQ0 | |
|---|---|---|
| Gene: | ABCG2 | |
| Actions: | inhibitor | |
| References: |
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Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
| UniProt ID: | Q9Y6L6 | ||||
|---|---|---|---|---|---|
| Gene: | SLCO1B1 | ||||
| Actions: | inhibitor | ||||
| References: |
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