Chemical Properties
White to Off-White Powder
Uses
Mycophenolic acid(24280-93-1) is a common Penicillium metabolite first reported in the 1930s as a possible mycotoxin. Re-investigation showed mycophenolic acid to display broad antitumour, antiviral, antifungal and antiprotozoan activities. Its potent immunosuppressant activity led to its commercial development to prevent kidney transplant rejection. Mycophenolic acid acts by inhibiting inosine monophosphate dehydrogenase, controlling the rate of de novo purine synthesis in proliferating B and T lymphocytes.
Uses
An antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleotides.
Uses
antineoplastic, progestin
Uses
immune suppressant, antineoplastic, antiviral
Definition
ChEBI: A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an
antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mo
etil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
Brand name
Myfortic (Novartis).
General Description
Assayed in therapeutic drug monitoring to ensure patients remain within the drug′s therapeutic range, mycophenolic acid is an immunosuppressant drug and the active metabolite of the prodrug mycophenolate mofetil. This analytical standard is suitable for LC-MS/MS applications including therapeutic drug monitoring and other clinical or diagnostic applications.
Biological Activity
Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo . Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation.
Mechanism of action
Mycophenolic acid (MPA,24280-93-1) is a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH) that prevents the ab initio biosynthesis of purine nucleotides. It predominantly affects lymphocytes, leading to inhibition of DNA synthesis in T cells and B cells, thereby suppressing cell-mediated immune responses and antibody formation.MPA also inhibits glycosylation and expression of adhesion molecules, as well as the recruitment of lymphocytes and monocytes to sites of inflammation.MPA depletes tetrahydrobiopterin and reduces nitric oxide production via inducible NO synthase without affecting the activity of constitutive NO synthase[1].
Purification Methods
Purify the acid by dissolving it in the minimum volume of EtOAc, applying onto a silica gel column (0.05-0.2 mesh) and eluting with a mixture of EtOAc/CHCl3/AcOH (45:55:1) followed by recrystallisation from heptane/EtOAc, from aqueous EtOH or from hot H2O and drying in vacuo. It is a weak dibasic acid, moderately soluble in Et2O, CHCl3 and hot H2O but weakly soluble in *C6H6 and toluene. [Birch & Wright Aust J Chem 22 2635 1969, Canonica et al. J Chem Soc, Perkin Trans 1 2639 1972, Birkinshaw et al. Biochem J 50 630 1952, Beilstein 18 II 393, 18 III/IV 6513.]
