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drugbank:absorption Rapidly absorbed following oral administration. In 12 healthy volunteers, the mean absolute bioavailability of oral mycophenolate mofetil relative to intravenous mycophenolate mofetil (based on MPA AUC) was 94%. Food (27 g fat, 650 calories) has no effect on the extent of absorption (MPA AUC) of mycophenolate mofetil.
drugbank:affectedOrganism Humans and other mammals
drugbank:ahfsCode 92:00.00
drugbank:atcCode L04AA06
drugbank:biotransformation Following oral and intravenous dosing, mycophenolate mofetil undergoes complete metabolism to MPA, the active metabolite. Metabolism to MPA occurs presystemically after oral dosing. MPA is metabolized principally by glucuronyl transferase to form the phenolic glucuronide of MPA (MPAG) which is not pharmacologically active. In vivo, MPAG is converted to MPA via enterohepatic recirculation. The following metabolites of the 2-hydroxyethyl-morpholino moiety are also recovered in the urine following oral administration of mycophenolate mofetil to healthy subjects: N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and the N-oxide of N-(2-hydroxyethyl)-morpholine.
drugbank:brandName CellCept
drugbank:brandName Munoloc
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/2339>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/4210>
drugbank:brandedDrug <http://wifo5-04.informatik.uni-mannheim.de/dailymed/resource/drugs/828>
drugbank:casRegistryNumber <http://bio2rdf.org/cas:128794-94-5>
drugbank:chemicalFormula C23H31NO7
drugbank:chemicalIupacName 2-morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
drugbank:contraindicationInsert <http://129.128.185.122/drugbank2/drugs/DB00688/inserts/1081/full>
drugbank:creationDate 2005-06-13 13:24:05 UTC
drugbank:description Mycophenolate mofetil is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent, inosine monophosphate dehydrogenase (IMPDH) inhibitor.
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drugbank:dpdDrugIdNumber 02240347
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drugbank:enzyme <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/enzymes/1>
drugbank:experimentalLogpHydrophobicity 2.5
drugbank:experimentalWaterSolubility Slightly soluble (43 mg/mL at pH 7.4)
drugbank:fdaLabelFiles 2000-07-01 /drugs/688/fda_labels/935 2000-12-01 /drugs/688/fda_labels/889
drugbank:foodInteraction Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
drugbank:foodInteraction Take on empty stomach: 1 hour before or 2 hours after meals.
drugbank:genericName Mycophenolate mofetil
drugbank:halfLife The mean elimination half-life for mycophenolic acid (the active metabolite) ranges from 8-16 hours, while that of the MPAG metabolite ranges from 13-17 hours.
drugbank:inchiIdentifier InChI=1/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+
drugbank:inchiKey RTGDFNSFWBGLEC-SYZQJQIIBO
drugbank:indication For the prophylaxis of organ rejection in patients receiving allogeneic renal, cardiac or hepatic transplants. Mycophenolate mofetil should be used concomitantly with cyclosporine and corticosteroids.
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drugbank:keggCompoundId <http://bio2rdf.org/cpd:C07908>
drugbank:keggDrugId <http://bio2rdf.org/kegg:D00752>
rdfs:label Mycophenolate mofetil
drugbank:limsDrugId 688
drugbank:massSpecFile 0
drugbank:mechanismOfAction Mycophenolate mofetil is hydrolyzed to form mycophenolic acid (MPA), which is the active metabolite. MPA is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, MPA has potent cytostatic effects on lymphocytes. MPA inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of MPA on lymphocytes. MPA also suppresses antibody formation by B-lymphocytes. MPA prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection. Mycophenolate mofetil did not inhibit early events in the activation of human peripheral blood mononuclear cells, such as the production of interleukin-1 (IL-1) and interleukin-2 (IL-2), but did block the coupling of these events to DNA synthesis and proliferation.
drugbank:molecularWeightAverage 433.4947
drugbank:molecularWeightMono 433.2101
foaf:page <http://dbpedia.org/page/Mycophenolate_mofetil>
foaf:page <http://en.wikipedia.org/wiki/Mycophenolate_mofetil>
foaf:page <http://www.drugbank.ca/drugs/DB00688>
drugbank:patientInformationInsert http://129.128.185.122/drugbank2/drugs/DB00688/inserts/266/full
drugbank:pharmacology Mycophenolate mofetil is a prodrug of mycophenolic acid, an antibiotic substance derived from <i>Penicillium stoloniferum</i>. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase. Mycophenolic acid is important because of its selective effects on the immune system. It prevents the proliferation of T-cells, lymphocytes, and the formation of antibodies from B-cells. It also may inhibit recruitment of leukocytes to inflammatory sites.
drugbank:pharmgkbId PA450567
drugbank:possibleDiseaseTarget <http://wifo5-04.informatik.uni-mannheim.de/diseasome/resource/diseases/3740>
drugbank:possibleDiseaseTarget <http://wifo5-04.informatik.uni-mannheim.de/diseasome/resource/diseases/992>
drugbank:predictedLogpHydrophobicity 2.17
drugbank:predictedLogs -3.66
drugbank:predictedWaterSolubility 9.50e-02 mg/mL
drugbank:primaryAccessionNo DB00688
drugbank:proteinBinding MPA (the active metabolite), at clinically relevant concentrations, is over 98% bound to plasma albumin.
drugbank:pubchemCompoundId 5281078
drugbank:pubchemSubstanceId 7847817
drugbank:reference
drugbank:rxlistLink <http://www.rxlist.com/cgi/generic3/cellcept.htm>
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owl:sameAs <http://dbpedia.org/resource/Mycophenolate_mofetil>
owl:sameAs <http://www.dbpedia.org/resource/Mycophenolic_acid>
drugbank:secondaryAccessionNumber aprd01602
drugbank:smilesStringCanonical COC1=C(CC=C(C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C
drugbank:smilesStringIsomeric COC1=C(CC=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C
drugbank:state Solid
drugbank:structure 1
drugbank:synonym Mycophenylate mofetil
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/796>
drugbank:target <http://wifo5-04.informatik.uni-mannheim.de/drugbank/resource/targets/838>
drugbank:toxicity Oral (LD50): Acute: 352 mg/kg [Rat], 1000 mg/kg [Mouse], and &gt;6000 mg/kg [Rabbit]. Possible signs and symptoms of acute overdose could include the following: hematological abnormalities such as leukopenia and neutropenia, and gastrointestinal symptoms such as abdominal pain, diarrhea, nausea and vomiting, and dyspepsia.
rdf:type drugbank:drugs
rdf:type vocabClass:Offer
drugbank:updateDate 2008-08-26 14:47:56 UTC