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drugbank: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.
drugbank:affectedOrganism Humans and other mammals
drugbank:ahfsCode 92:00.00
drugbank:atcCode L04AA01
drugbank:biotransformation Hepatic, extensively metabolized.
drugbank:brandName Gengraf (Abbott labs)
drugbank:brandName Neoral (Novartis)
drugbank:brandName Restasis
drugbank:brandName Restasis (Allergan Inc)
drugbank:brandName Sandimmune (Novartis)
drugbank:brandName Sangcya
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drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/235>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/3297>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/3595>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/3948>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/615>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/877>
drugbank:casRegistryNumber <http://bio2rdf.org/cas:59865-13-3>
drugbank:chebiId <http://bio2rdf.org/chebi:4031>
drugbank:chemicalFormula C62H111N11O12
drugbank:chemicalIupacName 30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
drugbank:contraindicationInsert <http://129.128.185.122/drugbank2/drugs/DB00091/inserts/1725/full>
drugbank:creationDate 2005-06-13 13:24:05 UTC
drugbank: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).
drugbank:dosageForm <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/dosageforms/capsuleOral>
drugbank:dosageForm <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/dosageforms/liquidIntravenous>
drugbank:dosageForm <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/dosageforms/solutionOral>
drugbank:dpdDrugIdNumber 00593257
drugbank:drugCategory <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugcategory/antifungalAgents>
drugbank:drugCategory <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugcategory/antirheumaticAgents>
drugbank:drugCategory <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugcategory/dermatologicAgents>
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drugbank:drugCategory <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugcategory/immunomodulatoryAgents>
drugbank:drugCategory <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugcategory/immunosuppressiveAgents>
drugbank:drugIdNumberPage <http://205.193.93.51/dpdonline/searchRequest.do?din=00593257>
drugbank:drugType <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugtype/approved>
drugbank:drugType <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugtype/biotech>
drugbank:drugType <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/drugtype/investigational>
drugbank:enzyme <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/enzymes/1>
drugbank:experimentalCaco2Permeability -6.05 [ADME Research, USCD]
drugbank:experimentalLogpHydrophobicity 2.92 [HANSCH,C ET AL. (1995)]
drugbank:fdaLabelFiles 2000-01-01 /drugs/91/fda_labels/957 2002-06-01 /drugs/91/fda_labels/248 2003-03-01 /drugs/91/fda_labels/521 2003-09-01 /drugs/91/fda_labels/729 2004-06-01 /drugs/91/fda_labels/490
drugbank:foodInteraction Avoid salt substitutes containing potassium.
drugbank:foodInteraction Avoid taking with grapefruit or grapefruit juice as grapefruit can significantly increase serum levels of this product.
drugbank:foodInteraction 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).
drugbank:foodInteraction Take without regard to meals.
drugbank:genericName Cyclosporine
drugbank:halfLife Biphasic and variable, approximately 7 hours (range 7 to 19 hours) in children and approximately 19 hours (range 10 to 27 hours) in adults.
drugbank:inchiIdentifier InChI=1/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/f/h63-66H
drugbank:inchiKey PMATZTZNYRCHOR-CCMIHKRJDW
drugbank:indication For treatment of transplant rejection, rheumatoid arthritis, severe psoriasis
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drugbank:interactionInsert <http://129.128.185.122/drugbank2/drugs/DB00091/inserts/2825/full>
drugbank:keggCompoundId <http://bio2rdf.org/cpd:C05086>
drugbank:keggDrugId <http://bio2rdf.org/kegg:D00184>
rdfs:label Cyclosporine
drugbank:limsDrugId 91
drugbank:massSpecFile 0
drugbank:mechanismOfAction Cyclosporine binds to cyclophillin. 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.
drugbank:meltingPoint 148-151 oC
drugbank:molecularWeightAverage 1202.6112
drugbank:molecularWeightMono 1201.8414
foaf:page <http://dbpedia.org/page/Cyclosporine>
foaf:page <http://en.wikipedia.org/wiki/Cyclosporine>
foaf:page <http://www.drugbank.ca/drugs/DB00091>
drugbank:patientInformationInsert http://129.128.185.122/drugbank2/drugs/DB00091/inserts/699/full
drugbank: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. Sandimmune (cyclosporine) also inhibits lymphokine production and release including interleukin-2.
drugbank:pharmgkbId PA449167
drugbank:possibleDiseaseTarget <http://wifo5-04.informatik.uni-mannheim.de/diseasome/resource/diseases/1907>
drugbank:possibleDiseaseTarget <http://wifo5-04.informatik.uni-mannheim.de/diseasome/resource/diseases/251>
drugbank:predictedLogpHydrophobicity 4.12
drugbank:predictedLogs -5.10
drugbank:predictedWaterSolubility 9.53e-03 mg/mL
drugbank:primaryAccessionNo DB00091
drugbank:proteinBinding Approximately 90% is bound to proteins, primarily lipoproteins.
drugbank:pubchemCompoundId 6435893
drugbank:pubchemSubstanceId 199551
drugbank:reference
drugbank:rxlistLink <http://www.rxlist.com/cgi/generic/cyclosporine.htm>
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owl:sameAs <http://dbpedia.org/resource/Cyclosporine>
owl:sameAs <http://www.dbpedia.org/resource/Ciclosporin>
drugbank:secondaryAccessionNumber biod00003
drugbank:secondaryAccessionNumber btd00003
drugbank:smilesStringCanonical CCC1NC(=O)C(C(O)C(C)CC=CC)N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
drugbank:smilesStringIsomeric CC[C@@H]1NC(=O)[C@@H]([C@H](O)[C@H](C)CC=CC)N(C)C(=O)[C@@H](C(C)C)N(C)C(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@@H](C)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
drugbank:state Liquid
drugbank:structure 1
drugbank:synonym Ciclosporin
drugbank:synonym Cyclosporin
drugbank:synonym Cyclosporin A
drugbank:synonym cyclosporine
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/1524>
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/1588>
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/3867>
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/3868>
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/421>
drugbank:toxicity The oral LD<sub>50</sub> is 2329 mg/kg in mice, 1480 mg/kg in rats, and > 1000 mg/kg in rabbits. The I.V. LD<sub>50</sub> is 148 mg/kg in mice, 104 mg/kg in rats, and 46 mg/kg in rabbits.
rdf:type drugbank:drugs
rdf:type vocabClass:Offer
drugbank:updateDate 2008-08-26 15:46:51 UTC