Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H20O6 |
Molecular Weight | 320.3371 |
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)=O
InChI
InChIKey=HPNSFSBZBAHARI-RUDMXATFSA-N
InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
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 |
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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 |
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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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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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Mycophenolate mofetil treatment accelerates recovery from experimental allergic encephalomyelitis. | 2001 Sep |
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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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Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
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Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus. | 2003 Jun 14 |
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The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA. | 2003 Jun 5 |
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Mycophenolic acid inhibits avian reovirus replication. | 2004 Oct |
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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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Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006 Jul 26 |
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Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. | 2007 Jun |
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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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Antiviral activity of indole derivatives. | 2009 Aug |
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Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives. | 2009 Jul 1 |
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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 |
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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LIVERTOX |
NBK548945
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NDF-RT |
N0000175613
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NCI_THESAURUS |
C2087
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L04AA06
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C574
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QL04AA06
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SUB09098MIG
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100000090388
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446541
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Mycophenolate
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m7682
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483-60-3
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7145
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MYCOPHENOLIC ACID
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)