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MYCOPHENOLATE MOFETIL

IUPAC Name: 2-morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate

Symbol: MM

Molecular Formula: C23H31NO7

Molecular weight: 433.5 g/mol

CAS No: 128794-94-5

ATC Code: L04AA06

Drug Class: Immuno Modulator

General Properties:

Mycophenolate mofetil is a carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is a prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases. It has a role as an immunosuppressive agent, a prodrug, an EC 1.1.1.205 (IMP dehydrogenase) inhibitor and an anticoronaviral agent. It is a gamma-lactone, a member of phenols, an ether, a carboxylic ester and a tertiary amino compound. It is functionally related to a mycophenolic acid and a 2-(morpholin-4-yl)ethanol.

Mycophenolate mofetil, also known as MMF or CellCept, is a prodrug of mycophenolic acid, and classified as a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH). This drug is an immunosuppressant combined with drugs such as [Cyclosporine] and corticosteroids to prevent organ rejection after hepatic, renal, and cardiac transplants. It is marketed by Roche Pharmaceuticals and was granted FDA approval for the prophylaxis of transplant rejection in 1995. In addition to the above uses, mycophenolate mofetil has also been studied for the treatment of nephritis and other complications of autoimmune diseases. Unlike another immunosuppressant class, the calcineurin inhibitors, MMF generally does not cause nephrotoxicity or fibrosis. Previously, mycophenolic acid (MPA) was administered to individuals with autoimmune diseases beginning in the 1970s, but was discontinued due to gastrointestinal effects and concerns over carcinogenicity. The new semi-synthetic 2-morpholinoethyl ester of MPA was synthesized to avoid the gastrointestinal effects associated with the administration of MPA. It demonstrates an increased bioavailability, a higher efficacy, and reduced gastrointestinal effects when compared to MPA.

Mycophenolate Mofetil is the morpholinoethyl ester of mycophenolic acid (MPA) with potent immunosuppressive properties. Mycophenolate stops T-cell and B-cell proliferation through selective inhibition of the de novo pathway of purine biosynthesis. In vivo, the active metabolite, MPA, reversibly inhibits inosine 5′-monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of guanine nucleotides. MPA displays high lymphocyte specificity and cytotoxicity due to the higher dependence of activated lymphocytes on both salvage and de novo synthesis of guanine nucleotides relative to other cell types. (NCI04)

Indication:

Mycophenolate belongs to a group of medicines known as immunosuppressive agents. It is used with other medicines (eg, cyclosporine, steroid medicine) to lower the body’s natural immunity in patients who receive organ transplants (eg, kidney, heart, or liver).

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