Mycophenolate mofetil (CHEM016794)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:43:54 UTC
Update Date2016-11-09 01:15:28 UTC
Accession NumberCHEM016794
Identification
Common NameMycophenolate mofetil
ClassSmall Molecule
DescriptionMycophenolate mofetil, also known as MMF or CellCept, is a prodrug of mycophenolic acid, and classified as a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH).[A180805] This drug is an immunosuppressant combined with drugs such as [Cyclosporine] and corticosteroids to prevent organ rejection after hepatic, renal, and cardiac transplants.[L7363] It is marketed by Roche Pharmaceuticals and was granted FDA approval for the prophylaxis of transplant rejection in 1995.[A180826] 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.[A180799,A180805] 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.[A180826] 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.[A180826]
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoateChEBI
CellceptChEBI
MMFChEBI
Mycophenolic acid morpholinoethyl esterChEBI
RS 61443ChEBI
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acidGenerator
Mycophenolate morpholinoethyl esterGenerator
Mycophenolic acid mofetilGenerator
Mycophenylate mofetilHMDB
Mycophenolate sodiumHMDB
MyforticHMDB
Sodium mycophenolateHMDB
Mycophenolate mofetil hydrochlorideHMDB
Mofetil hydrochloride, mycophenolateHMDB
Mofetil, mycophenolateHMDB
Mycophenolate, sodiumHMDB
Mycophenolic acidHMDB
Chemical FormulaC23H31NO7
Average Molecular Mass433.495 g/mol
Monoisotopic Mass433.210 g/mol
CAS Registry Number128794-94-5
IUPAC Name2-(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
Traditional Namemycophenolate mofetil
SMILESCOC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C
InChI IdentifierInChI=1S/C23H31NO7/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/b15-4+
InChI KeyRTGDFNSFWBGLEC-SYZQJQIISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassIsobenzofuranones
Direct ParentPhthalides
Alternative Parents
Substituents
  • Phthalide
  • Anisole
  • Alkyl aryl ether
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Morpholine
  • Oxazinane
  • Fatty acyl
  • Benzenoid
  • Vinylogous acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.095 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.1 m³·mol⁻¹ChemAxon
Polarizability45.55 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w4i-2393200000-d549469b4d276b82f0a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0itd-4629600000-670072fd9bb0a49d7de1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-1741900000-022d7009668cda105e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0743900000-133a311844263f919bddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1961100000-5da439d2a9f8cae8f445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-9740100000-6af6a8b42b2977762a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0419700000-cbea334d70b0f1f93d90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-2859500000-742b323b12fbfbe7a502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe3-9564000000-dd2d4e0510f30a121c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0020900000-038b179f46cd4955dd10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0291200000-8369d80f2ca22af88fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0960100000-828ad4ec3f0767246892Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0501900000-6ec023ec52bc4a8e5ea1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-2921100000-7173e63d30a5885f9a87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-1590000000-77b54540de37ccf344ecSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00688
HMDB IDHMDB0014826
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMycophenolate_mofetil
Chemspider ID4444535
ChEBI ID8764
PubChem Compound ID5281078
Kegg Compound IDC07908
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8.
2. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv.
3. FDA label
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11099793
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11490743
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15572389
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15992049
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16979992
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19858585
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21180633
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21710356
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22081165
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22294686
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310598
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22417996
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22460418
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22560143
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=8826401
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9274835