Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H31NO7 |
Molecular Weight | 433.4947 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)OCCN3CCOCC3
InChI
InChIKey=RTGDFNSFWBGLEC-SYZQJQIISA-N
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+
Mycophenolic acid (MPA) possesses antibacterial, antifungal, antiviral, immunosuppressive and anticancer properties. Mycophenolic acid (MPA) is a fungal metabolite that was initially discovered by Bartolomeo Gosio in 1893 as an antibiotic against anthrax bacillus, Bacillus anthracis. It is an uncompetitive and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation to DNA. It was approved under the brand name Myfortic for the prophylaxis of organ rejection in adult patients receiving a kidney transplant and is indicated for the prophylaxis of organ rejection in pediatric patients 5 years of age and older who are at least 6 months post kidney transplant. Myfortic is to be used in combination with cyclosporine and corticosteroids.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21398490
Curator's Comment: by Bartolomeo Gosio in 1893
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111369 |
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Target ID: CHEMBL2111369 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11880114 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | MYFORTIC Approved UseMyfortic (mycophenolic acid) is indicated for the prophylaxis of organ rejection in adult patients receiving a kidney transplant. Myfortic is indicated for the prophylaxis of organ rejection in pediatric patients 5 years of age and older who are at least 6 months post kidney transplant. Myfortic is to be used in combination with cyclosporine and corticosteroids. Launch Date1.07783999E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.9 μg/mL |
720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered: CYCLOSPORINE |
MYCOPHENOLIC ACID unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
57.4 μg × h/mL |
720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered: CYCLOSPORINE |
MYCOPHENOLIC ACID unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.7 h |
720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MYCOPHENOLIC ACID unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0 |
weak [Ki 57 uM] | |||
weak [Ki 98 uM] |
Drug as victim
PubMed
Title | Date | PubMed |
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Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid. | 1990 Feb |
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Polymerase substrate depletion: a novel strategy for inhibiting the replication of the human immunodeficiency virus. | 1995 Aug 20 |
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Abacavir and mycophenolic acid, an inhibitor of inosine monophosphate dehydrogenase, have profound and synergistic anti-HIV activity. | 1999 Aug 15 |
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Novel mycophenolic adenine bis(phosphonate)s as potential immunosuppressants. | 1999 Jul |
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The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair. | 2000 Mar |
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Mycophenolate mofetil and its mechanisms of action. | 2000 May |
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Inosine-5'-monophosphate dehydrogenase is required for mitogenic competence of transformed pancreatic beta cells. | 2001 Jan |
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Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro. | 2001 Nov |
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Identification of active antiviral compounds against a New York isolate of West Nile virus. | 2002 Jul |
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Dose proportional inhibition of HIV-1 replication by mycophenolic acid and synergistic inhibition in combination with abacavir, didanosine, and tenofovir. | 2002 Jul |
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Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents. | 2002 Nov |
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Mycophenolic acid inhibits IL-2-dependent T cell proliferation, but not IL-2-dependent survival and sensitization to apoptosis. | 2002 Sep 1 |
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Anti-HIV-1 activity of leflunomide: a comparison with mycophenolic acid and hydroxyurea. | 2003 Jul 25 |
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Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus. | 2003 Jun 14 |
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Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. | 2004 Dec |
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In vitro combination of amdoxovir and the inosine monophosphate dehydrogenase inhibitors mycophenolic acid and ribavirin demonstrates potent activity against wild-type and drug-resistant variants of human immunodeficiency virus type 1. | 2004 Nov |
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Mycophenolic acid inhibits avian reovirus replication. | 2004 Oct |
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Mechanisms of action of mycophenolate mofetil. | 2005 |
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Synergy between imatinib and mycophenolic acid in inducing apoptosis in cell lines expressing Bcr-Abl. | 2005 Apr 15 |
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Mycophenolic acid inhibits syncytium formation accompanied by reduction of gp120 expression. | 2005 Aug |
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[Mycophenolic acid induced apoptosis in T lymphocytic cells Molt-4 and its mechanism]. | 2005 Jul |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. | 2005 May |
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Mycophenolic acid induces islet apoptosis by regulating mitogen-activated protein kinase activation. | 2006 Dec |
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Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006 Jul 26 |
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Conversion from mycophenolate mofetil to enteric-coated mycophenolate sodium in maintenance renal transplant recipients receiving tacrolimus: clinical, pharmacokinetic, and pharmacodynamic outcomes. | 2007 Feb 27 |
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Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. | 2007 Jun |
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Current target ranges of mycophenolic acid exposure and drug-related adverse events: a 5-year, open-label, prospective, clinical follow-up study in renal allograft recipients. | 2008 Apr |
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Effect of D256N and Y483D on propofol glucuronidation by human uridine 5'-diphosphate glucuronosyltransferase (UGT1A9). | 2008 Aug |
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Mycophenolic acid inhibits cell proliferation and extracellular matrix synthesis in rat vascular smooth muscle cells through direct and indirect inhibition of cellular reactive oxygen species. | 2008 Nov |
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The necrotic signal induced by mycophenolic acid overcomes apoptosis-resistance in tumor cells. | 2009 |
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Antiviral activity of indole derivatives. | 2009 Aug |
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[Wegener's granulomatosis and microscopic polyangiitis]. | 2009 Feb |
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Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives. | 2009 Jul 1 |
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Mycophenolic acid in rheumatology: mechanisms of action and severe adverse events. | 2010 Apr-Jun |
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Inflammation-associated gene transcription and expression in mouse lungs induced by low molecular weight compounds from fungi from the built environment. | 2010 Jan 5 |
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Mycophenolic acid inhibits the phosphorylation of NF-kappaB and JNKs and causes a decrease in IL-8 release in H2O2-treated human renal proximal tubular cells. | 2010 May 14 |
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Mycophenolic acid inhibits natural killer cell proliferation and cytotoxic function: a possible disadvantage of including mycophenolate mofetil in the graft-versus-host disease prophylaxis regimen. | 2011 Feb |
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Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines. | 2013 Nov |
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Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases. | 2014 Jul |
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Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function. | 2015 Dec 25 |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
Patents
Sample Use Guides
Dosage in Adult Kidney Transplant Patients: the recommended dose of Myfortic is 720 mg administered twice daily (1440 mg total daily dose). Dosage in Pediatric Kidney Transplant Patients: the recommended dose of Myfortic in conversion (at least 6 months post-transplant) pediatric patients age 5 years and older is 400 mg/m2 body surface area (BSA) administered twice daily (up to a maximum dose of 720 mg administered twice daily. Administration Myfortic tablets should be taken on an empty stomach, 1 hour before or 2 hours after food intake
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27259985
It was investigated the antiviral activity and mechanism of action of mycophenolic acid (MPA) against contemporary clinical isolates of influenza A and B viruses. The 50 % cellular cytotoxicity (CC50) of MPA in Madin Darby canine kidney cell line was over 50 µM. MPA prevented influenza virus-induced cell death in the cell-protection assay, with significantly lower IC50 for influenza B virus B/411 than that of influenza A(H1N1)pdm09 virus H1/415 (0.208 vs 1.510 µM, P=0.0001). For H1/415, MPA interfered with the early stage of viral replication before protein synthesis. For B/411, MPA may also act at a later stage since MPA was active against B/411 even when added 12 h post-infection. Virus-yield reduction assay showed that the replication of B/411 was completely inhibited by MPA at concentrations ≥0.78 µM, while there was a dose-dependent reduction of viral titer for H1/415. The antiviral effect of MPA was completely reverted by guanosine supplementation. Plaque reduction assay showed that MPA had antiviral activity against eight different clinical isolates of A(H1N1), A(H3N2), A(H7N9) and influenza B viruses (IC50 <1 µM).
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
MYCOPHENOLATE MOFETIL (AUTHORIZED: GRAFT REJECTION)
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EMA ASSESSMENT REPORTS |
CELLCEPT (AUTHORIZED: GRAFT REJECTION)
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FDA ORPHAN DRUG |
223106
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NCI_THESAURUS |
C574
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FDA ORPHAN DRUG |
215405
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NCI_THESAURUS |
C2087
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EMA ASSESSMENT REPORTS |
MYFENAX (AUTHORIZED: GRAFT REJECTION)
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EMA ASSESSMENT REPORTS |
MYCLAUSEN (AUTHORIZED: GRAFT REJECTION)
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140401-05-4
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MYCOPHENOLATE MOFETIL
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C1468
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100000092752
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1448956
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DB00688
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724229
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7436
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68149
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5281078
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CC-26
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CHEMBL1456
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m7682
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SUB03360MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD