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Mycophenolate mofetil

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Title: Mycophenolate mofetil  
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Subject: Inosine, Hypomagnesemia, MMF, Membranous glomerulonephritis, Autoimmune lymphoproliferative syndrome, Purine metabolism
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Mycophenolate mofetil

Template:Chembox ChEMBL
Mycophenolate mofetil
Identifiers
CAS number 128794-94-5 YesY
PubChem 5281078
ChemSpider 4444535 YesY
DrugBank DB00688
KEGG C07908 YesY
ChEBI CHEBI:8764 YesY
Jmol-3D images Image 1
Properties
Molecular formula C23H31NO7
Molar mass 433.49474
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Mycophenolate mofetil (MMF) (brand name CellCept, compare with Myfortic - natrii mycophenolas) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. It is a reversible inhibitor of inosine monophosphate dehydrogenase[1] (IMPDH) in purine (guanine) biosynthesis which is necessary for the growth of T cells and B cells. Other cells are able to recover purines via a separate scavenger pathway and are thus able to escape the effect.

MMF is also used in the treatment of autoimmune diseases, such as Behçet's disease, pemphigus vulgaris, systemic lupus erythematosus and refractory incomplete lupus erythematosus.[2] Suppressing T cells and B cells stops them from attacking healthy cells, but also weakens their ability to defend against infections.

MMF became popular as a less toxic alternative, instead of or in addition to azathioprine and cyclophosphamide.

The chemical name for mycophenolate mofetil is 2-morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate. Its empirical formula is C23H31NO7 and molecular weight 433.50. Mycophenolate mofetil is morpholinoethyl ester of mycophenolic acid, which is used to mask the carboxyl group. Mycophenolate mofetil is reported to have pKa values 5.6 for the morpholino moiety and 8.5 for the phenolic group.[3]

Side-effects and adverse reactions

Among the most common side-effects of this drug are high blood sugars and increased blood cholesterol levels. Other changes in blood chemistry such as hypomagnesemia, hypocalcemia, hyperkalemia, and an increase in BUN are regularly noted. Coughing and issues with breathing are not uncommon - pleural effusions being noted in approximately 1:3. There is a similar occurrence ratio of Infections; with leukopenia and anemia reflecting the immunosuppressive and myelosuppressive nature of the drug. Back and abdominal pain - in addition to headache, nausea, diarrhea, and fever - are also experienced with this drug.

More rarely, various neoplasia occur: melanoma, lymphoma, other malignancies having an occurrences of 1 in 20 to 1 in 200, depending on the type, with Neoplasia in the skin being the most common site.

Other rarer effects include gastrointestinal bleeding and pulmonary fibrosis.

Progressive multifocal leukoencephalopathy is a usually fatal infection of the brain that occurs rarely with this and other immunosuppressive drugs.

Given that this is a pro-drug of mycophenolic acid, the adverse reactions and side-effects noted in that article are also relevant.

Apart from Medscape,[4] the British National Formulary[5] March 2011 was consulted in drafting these side-effects.

References

ru:Микофенолата мофетил

sr:Mikofenolate mofetil

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