Natural Product (NP) Details

General Information of the NP (ID: NP5160)
Name
Mycophenolate mofetil
Synonyms
mycophenolate mofetil; 128794-94-5; CellCept; RS 61443; 115007-34-6; RS-61443; TM-MMF; Myfenax; Mycophenolic acid morpholinoethyl ester; Mycophenolatemofetil; UNII-9242ECW6R0; CHEBI:8764; Cellcept (TN); 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; 2-morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate; 2-Morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate; (E)-2-Morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate; Mycophenolate mofetil (CellCept); 9242ECW6R0; MFCD00867568; C23H31NO7; Munoloc; RS-61443-190; DSSTox_CID_3340; DSSTox_RID_76982; Mycophenolate mofetil, 98%; DSSTox_GSID_23340; 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl ester, (4E)-; 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl ester, (E)-; Mycophenylate mofetil; 2-morpholin-4-ylethyl (4E)-6-[4-hydroxy-7-methyl-6-(methyloxy)-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate; SMR002544686; MMF CellCept(TM); CAS-128794-94-5; HSDB 7436; ME-MPA; SR-05000001485; Mycophenolate mofetil Teva; Arzip; Mycophenolatmofetil; Mycophenolate mofetil [USAN:USP]; NCGC00159459-02; (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-4-hexenoic acid 2-(4-morpholinyl)ethyl ester; 2-morpholin-4-ylethyl (E)-6-(6-methoxy-7-methyl-4-oxidanyl-3-oxidanylidene-1H-2-benzofuran-5-yl)-4-methyl-hex-4-enoate; mycophenolate-mofetil; Mofetil mycophenolate; 1132748-21-0; R-99; SCHEMBL4195; CHEMBL1456; MLS003915627; MLS004774133; MLS006011929; SCHEMBL218782; GTPL6831; DTXSID3023340; CHEBI:93612; Mycophenolate mofetil(CellCept)/; AOB5505; Mycophenolate mofetil (JAN/USP); HMS2090A03; Pharmakon1600-01504567; ACT01993; ALBB-027273; HY-B0199; Tox21_111686; ABP000539; BBL029073; BDBM50248299; NSC724229; NSC758905; s1501; STL146382; ZINC21297660; AKOS005720900; Tox21_111686_1; AB07560; AC-1562; BCP9000969; CCG-213315; DB00688; KS-1209; NSC 724229; NSC 758905; NSC-724229; NSC-758905; Mycophenolate mofetil, >=98% (HPLC); NCGC00159459-03; NCGC00159459-04; 2-morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate; 2-morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-hex-4-enoate; LS-15013; SMR004703518; AB0125583; M2387; R3925; SW219893-1; C07908; D00752; J90063; AB01274794-01; AB01274794-02; AB01274794_03; AB01274794_04; 007M346; A803280; A805863; J-005626; Mycophenolate mofetil 100 microg/mL in Acetonitrile; Q-101316; Q4567614; SR-05000001485-1; SR-05000001485-2; BRD-K92428153-001-01-0; MYCOPHENOLIC ACID 2-(4-MORPHOLINYL)ETHYL ESTER; Mycophenolate mofetil, European Pharmacopoeia (EP) Reference Standard; Mycophenolate mofetil, United States Pharmacopeia (USP) Reference Standard; Mycophenolate mofetil for peak identification, European Pharmacopoeia (EP) Reference Standard; Mycophenolate Mofetil, Pharmaceutical Secondary Standard; Certified Reference Material; (1s,3r,4s)-2-amino-9-[4-(benzyloxy)-3-(benzyloxymethyl)-2-methylidene-cyclopentyl]-3h-purin-6-one; (E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-Morpholinyl)ethyl Ester; 1076198-64-5; 2-(4-Morpholinyl)ethyl (E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate; 2-morpholin-4-ylethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate; 2-Morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate; 4-Hexenoic acid,3-dihydro-4-hydroxy-6-methoxy-7-methyl -3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl ester, (4E); 6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid 2-(4-morpholinyl)ethyl ester; morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate; Morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)- 4-methylhex-4-enoate; Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate; Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate
    Click to Show/Hide
Species Origin Penicillium stoloniferum ...     Click to Show/Hide
Penicillium stoloniferum
Kingdom: Fungi
Phylum: Ascomycota
Class: Eurotiomycetes
Order: Eurotiales
Family: Aspergillaceae
Genus: Penicillium
Species: Penicillium stoloniferum
Disease Transplant rejection [ICD-11: NE84] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C23H31NO7
PubChem CID
5281078
Canonical SMILES
CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OCCN3CCOCC3)O
InChI
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+
InChIKey
RTGDFNSFWBGLEC-SYZQJQIISA-N
CAS Number
CAS 128794-94-5
ChEBI ID
CHEBI:8764
TTD Drug ID
D04FBR
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Rapamycin      Multiple myeloma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model The left kidney of the donor rat (Fisher F344) was perfused through the aorta with 4 degree centigrade heparinized Ringer's lactate solution and harvested, after transecting the ureter, the renal artery close to the aorta, and the renal vein near the vena cava. The recipient rat was anesthetized and a left nephrectomy was performed after transecting the renal artery, the renal vein, and the ureter.
                    Experimental
                    Result(s)		 Over a 50-week study, concomitant therapy of MMF and RAPA prevents chronic renal allograft rejection, probably through reduction of ischemic and cytotoxic degenerative changes.
          Cyclosporin      Psoriasis vulgaris     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 The introduction of MMF combined with the reduction of at least 50% of CNI dose allowed the renal function of liver transplant recipients to significantly improve at 1 year, without any rejection episode and without significant secondary effects.
          Prednisolone      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Triple combination immunosuppressive therapy maintained with additional mycophenolate mofetil successfully controlled recurrent myocarditis, enabled a reduction in the prednisolone dose, and achieved the functional recovery of the left ventricle.
          Mizoribine      Transplant rejection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model T-cell populations from B6 mice Healthy Rattus norvegicus
                    In-vivo Model Heterotopic vascularized heart transplantation was performed into the right cervical portion of the B6 mice.
                    Experimental
                    Result(s)		 The combination of MMF and MZ showed mild synergistic effects in the inhibition of MLR and strong synergistic effects in a mouse heart transplantation model.
          Tacrolimus      Transplant rejection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 The introduction of MMF combined with the reduction of at least 50% of CNI dose allowed the renal function of liver transplant recipients to significantly improve at 1 year, without any rejection episode and without significant secondary effects.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Losartan      Hypertension     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression AGTRAP  Molecule Info 
Pathway MAP
                    In-vivo Model Male Sprague-Dawley rats, weighing 225 to 250 g were used in this study.
                    Experimental
                    Result(s)		 MMF treatment decreases CsA-induced nephrotoxicity, and combined treatment with LSRT has a synergistic effect in preventing chronic CsA nephrotoxicity.
          Everolimus      Renal cell carcinoma     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 This regimen was proven to be efficient to prevent and treat nephrotoxicity and neurotoxicity with an acceptable tolerability profile.
Target and Pathway
Target(s) IMP dehydrogenase 2 (IMPDH2)  Molecule Info  [9]
Prostaglandin E2 receptor EP2 (PTGER2)  Molecule Info  [10]
BioCyc Purine nucleotides degradation Click to Show/Hide
2 Urate biosynthesis/inosine 5'-phosphate degradation
3 Guanosine nucleotides de novo biosynthesis
4 Superpathway of purine nucleotide salvage
5 Purine nucleotides de novo biosynthesis
6 Guanosine ribonucleotides de novo biosynthesis
KEGG Pathway Purine metabolism Click to Show/Hide
2 Drug metabolism - other enzymes
3 Metabolic pathways
4 cAMP signaling pathway
5 Neuroactive ligand-receptor interaction
6 Inflammatory mediator regulation of TRP channels
7 Renin secretion
8 Pathways in cancer
Panther Pathway De novo purine biosynthesis Click to Show/Hide
Reactome Purine ribonucleoside monophosphate biosynthesis Click to Show/Hide
2 Prostanoid ligand receptors
3 G alpha (s) signalling events
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 Ovarian Infertility Genes
4 Small Ligand GPCRs
5 GPCR ligand binding
6 GPCR downstream signaling
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6831).
Reference 2 Combination therapy of mycophenolate mofetil and rapamycin in prevention of chronic renal allograft rejection in the rat. Transplantation. 2003 Jan 15;75(1):54-9.
Reference 3 Mycophenolate mofetil in combination with reduction of calcineurin inhibitors for chronic renal dysfunction after liver transplantation. Liver Transpl. 2006 Dec;12(12):1755-60.
Reference 4 Combination treatment with corticosteroid, cyclosporine A, and mycophenolate in refractory nephrotic syndrome. Clin Nephrol. 2011 Jun;75(6):511-7.
Reference 5 Successful Triple Combination Immunosuppressive Therapy with Prednisolone, Cyclosporine, and Mycophenolate Mofetil to Treat Recurrent Giant Cell Myocarditis. Intern Med. 2019 Jul 15;58(14):2035-2039.
Reference 6 Combination effect of mycophenolate mofetil with mizoribine on cell proliferation assays and in a mouse heart transplantation model. Transplantation. 2006 Jul 27;82(2):175-9.
Reference 7 Synergistic effects of mycophenolate mofetil and losartan in a model of chronic cyclosporine nephropathy. Transplantation. 2003 Feb 15;75(3):309-15.
Reference 8 Everolimus plus mycophenolate mofetil as initial immunosuppression in liver transplantation. Transplant Proc. Jan-Feb 2015;47(1):90-2.
Reference 9 Clinical pipeline report, company report or official report of Roche (2009).
Reference 10 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 341).
 Download Picture         KEGG Link      
 Download Picture         KEGG Link