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
Thumb
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
PropertyValueSource
Water Solubility0.095 mg/mLALOGPS
logP2.17ALOGPS
logP3.47ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)6.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.53 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.1 m3·mol-1ChemAxon
Polarizability45.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon