- Mycophenolate mofetil
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Mycophenolate mofetil 
Identifiers CAS number 128794-94-5 
PubChem 5281078 ChemSpider 4444535 DrugBank DB00688 ChEMBL CHEMBL1456 Jmol-3D images Image 1 - CC1=C(C(=C(C2=C1COC2=O)O)CC=C(C)CCC(=O)OCCN3CCOCC3)OC
- InChI=1S/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+
Key: RTGDFNSFWBGLEC-SYZQJQIISA-N
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+
Key: RTGDFNSFWBGLEC-SYZQJQIIBO
Properties Molecular formula C23H31NO7 Molar mass 433.49474 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) 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 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 a less toxic alternative to azathioprine.
MMF is also used in the treatment of autoimmune diseases, such as Behçet's disease, pemphigus vulgaris and systemic lupus erythematosus. Suppressing T cells and B cells stops them from attacking healthy cells, but also weakens their ability to defend against infections.
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.[2]
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. Neoplasia in the skin being the most common site.
Other rarer effects include GI bleeding, and pulmonary fibrosis.
Progressive multifocal leukoencephalopathy is a usually fatal infection of the brain which 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[3], the British National Formulary[4] March 2011 was consulted in drafting these side-effects.
References
- ^ Fulton B, Markham A. "Mycophenolate mofetil : a review of its pharmacodynamic and pharmacokinetic properties and clinical efficacy in renal transplantation." Drugs. 1996, 51(2):278-98.
- ^ http://www.rocheusa.com/products/cellcept/pi.pdf
- ^ http://reference.medscape.com/drug/cellcept-myfortic-mycophenolate-343209#4
- ^ www.bnf.org
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