Mycophenolate mofetil hydrochlorideProduct ingredient for Mycophenolate mofetil
- Name
- Mycophenolate mofetil hydrochloride
- Drug Entry
- Mycophenolate mofetil
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).3 This drug is an immunosuppressant combined with drugs such as Cyclosporine and corticosteroids to prevent organ rejection after hepatic, renal, and cardiac transplants.13 It is marketed by Roche Pharmaceuticals and was granted FDA approval for the prophylaxis of transplant rejection in 1995.6 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.2,3
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.6 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.6
- Accession Number
- DBSALT001477
- Structure
- Synonyms
- Mycophenolate mofetil HCl
- UNII
- UXH81S8ZVB
- CAS Number
- 116680-01-4
- Weight
- Average: 469.96
Monoisotopic: 469.1867301 - Chemical Formula
- C23H32ClNO7
- InChI Key
- OWLCGJBUTJXNOF-HDNKIUSMSA-N
- InChI
- InChI=1S/C23H31NO7.ClH/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;1H/b15-4+;
- IUPAC Name
- 2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate hydrochloride
- SMILES
- Cl.COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C
- External Links
- ChemSpider
- 4945251
- ChEMBL
- CHEMBL1200955
- Wikipedia
- Mycophenolic_acid
- Predicted Properties
Property Value Source Water Solubility 0.095 mg/mL ALOGPS logP 2.17 ALOGPS logP 3.47 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 9.76 Chemaxon pKa (Strongest Basic) 6.19 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 94.53 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 117.1 m3·mol-1 Chemaxon Polarizability 45.79 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon