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Mycophenolic acid
Mycophenolic acid2
2D structure
1JR1 - Mycophenolic acid
3D crystal structure based on PDB 1JR1[1]

Synonyms

Lilly-68618, MPA, Mycophenolate, NSC-129185

Brand names

Myfortic

IUPAC name

IUPAC name
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

ChemSpider

393865

DrugBank

DB01024

PubChem

446541

PDB fields

PDBs
1JR1 (RCSB, PDBe; X-ray)
1ME7 (RCSB, PDBe; X-ray)
1MEI (RCSB, PDBe; X-ray)
1MEH (RCSB, PDBe; X-ray)
4FO4 (RCSB, PDBe; X-ray)
4FXS (RCSB, PDBe; X-ray)
4AF0 (RCSB, PDBe; X-ray)

InChI

InChI
1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+

InChIKey

InChIKey
HPNSFSBZBAHARI-RUDMXATFSA-N

SMILES

SMILES
COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C
(Jmol 3D structure)

Formula

C17H20O6

Mol. mass

320.3371 g/mol

MeSH

D009173


Penicillium brevicompactum

Penicillium brevicompactum, the natural source of mycophenolic acid

Mycophenolic acid is an antibiotic substance with immunosuppressant properties that is derived from the fungus, Penicillium brevicompactum and related species.[2] It exerts its immunosuppresant effects by inhibiting the enzyme inosine monophosphate dehydrogenase (which is required for de novo purine synthesis), leading to reduced lymphocyte proliferation and antibody synthesis.[2] It is primarily used to prevent organ rejection in organ transplant recipients in combination with a calcineurin inhibitor and prednisone (where it has been used to replace azathioprine in this three-drug immunosuppressant cocktail, as mycophenolic acid/mycophenolate mofetil is associated with a lower rate of organ rejection when compared to azathioprine), but it also used as an immunosuppressant in the management of systemic lupus erythematosus.[2][3] Mycophenolate mofetil is a preparation that is metabolized in vivo into mycophenolic acid and is distinguished from straight mycophenolic acid mostly based on its pharmacokinetic properties.[3]



External linksEdit

Reference listEdit

  1. Sintchak, MD; Fleming, MA; Futer, O; Raybuck, SA; Chambers, SP; Caron, PR; Murcko, MA; Wilson, KP (14 June 1996). "Structure and mechanism of inosine monophosphate dehydrogenase in complex with the immunosuppressant mycophenolic acid.". Cell 85 (6): 921-30. doi:10.1016/S0092-8674(00)81275-1. PDB: 1JR1 (RCSB PDB, PDBe)PMID 8681386.
  2. 2.0 2.1 2.2 Kilbourne, J; Case, JT; Cho, DS; Hui, C; Jarnot, M; Koroma, B; Pash, J; Powell, T; Schulman, JL; Sorden, N (2015). "Mycophenolic Acid". Medical Subject Headings. Bethesda, USA: U.S. National Library of Medicine. Retrieved 20 November 2014. 
  3. 3.0 3.1 Brayfield, A, ed. (8 April 2014). "Mycophenolate". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 20 November 2014. 

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