U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H20O6
Molecular Weight 320.3378
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MYCOPHENOLIC ACID

SMILES

C/C(=C(/[H])\Cc1c(c2c(COC2=O)c(C)c1OC)O)/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+

HIDE SMILES / InChI
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

Curator's Comment:: by Bartolomeo Gosio in 1893

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MYFORTIC

Approved Use

Myfortic (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 Date

1.07783999E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
major
minor
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [Km 1390 uM]
yes [Km 160 uM]
yes [Km 200 uM]
yes [Km 410 uM]
yes [Km 480 uM]
yes
PubMed

PubMed

TitleDatePubMed
Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid.
1990 Feb
Polymerase substrate depletion: a novel strategy for inhibiting the replication of the human immunodeficiency virus.
1995 Aug 20
Abacavir and mycophenolic acid, an inhibitor of inosine monophosphate dehydrogenase, have profound and synergistic anti-HIV activity.
1999 Aug 15
Novel mycophenolic adenine bis(phosphonate)s as potential immunosuppressants.
1999 Jul
The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair.
2000 Mar
Inosine-5'-monophosphate dehydrogenase is required for mitogenic competence of transformed pancreatic beta cells.
2001 Jan
Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.
2001 Nov
Mycophenolate mofetil treatment accelerates recovery from experimental allergic encephalomyelitis.
2001 Sep
Identification of active antiviral compounds against a New York isolate of West Nile virus.
2002 Jul
Dose proportional inhibition of HIV-1 replication by mycophenolic acid and synergistic inhibition in combination with abacavir, didanosine, and tenofovir.
2002 Jul
Characterization of wild-type and cidofovir-resistant strains of camelpox, cowpox, monkeypox, and vaccinia viruses.
2002 May
Discovery of N-[2-[2-[[3-methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a novel and potent inhibitor of inosine monophosphate dehydrogenase with excellent in vivo activity.
2002 May 23
Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents.
2002 Nov
Mycophenolic acid inhibits IL-2-dependent T cell proliferation, but not IL-2-dependent survival and sensitization to apoptosis.
2002 Sep 1
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Anti-HIV-1 activity of leflunomide: a comparison with mycophenolic acid and hydroxyurea.
2003 Jul 25
Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus.
2003 Jun 14
The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA.
2003 Jun 5
Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5.
2004 Dec
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
Mycophenolic acid inhibits avian reovirus replication.
2004 Oct
Mechanisms of action of mycophenolate mofetil.
2005
Synergy between imatinib and mycophenolic acid in inducing apoptosis in cell lines expressing Bcr-Abl.
2005 Apr 15
Mycophenolic acid inhibits syncytium formation accompanied by reduction of gp120 expression.
2005 Aug
[Mycophenolic acid induced apoptosis in T lymphocytic cells Molt-4 and its mechanism].
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study.
2005 May
Mycophenolic acid induces islet apoptosis by regulating mitogen-activated protein kinase activation.
2006 Dec
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.
2006 Jul 26
Conversion from mycophenolate mofetil to enteric-coated mycophenolate sodium in maintenance renal transplant recipients receiving tacrolimus: clinical, pharmacokinetic, and pharmacodynamic outcomes.
2007 Feb 27
Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells.
2007 Jun
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
Effect of D256N and Y483D on propofol glucuronidation by human uridine 5'-diphosphate glucuronosyltransferase (UGT1A9).
2008 Aug
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
The necrotic signal induced by mycophenolic acid overcomes apoptosis-resistance in tumor cells.
2009
Antiviral activity of indole derivatives.
2009 Aug
[Wegener's granulomatosis and microscopic polyangiitis].
2009 Feb
Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives.
2009 Jul 1
Mycophenolic acid in rheumatology: mechanisms of action and severe adverse events.
2010 Apr-Jun
Inflammation-associated gene transcription and expression in mouse lungs induced by low molecular weight compounds from fungi from the built environment.
2010 Jan 5
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
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
Intracellular GTP level determines cell's fate toward differentiation and apoptosis.
2011 Jun 15
Effects of mycophenolic acid alone and in combination with its metabolite mycophenolic acid glucuronide on rat embryos in vitro.
2013 Feb
Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines.
2013 Nov
Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases.
2014 Jul
Transcriptome-based functional classifiers for direct immunotoxicity.
2014 Mar
Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function.
2015 Dec 25
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
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).
Name Type Language
MYCOPHENOLIC ACID
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
MYCOPHENOLATE [VANDF]
Common Name English
4-HEXENOIC ACID, 6-(1,3-DIHYDRO-4-HYDROXY-6-METHOXY-7-METHYL-3-OXO-5-ISOBENZOFURANYL)-4-METHYL-, (E)-
Common Name English
MYCOPHENOLATE MOFETIL SPECIFIED IMPURITY F [EP]
Common Name English
MYCOPHENOLATE
VANDF  
Common Name English
MYCOPHENOLIC ACID [MART.]
Common Name English
NSC-129185
Code English
MYCOPHENOLIC ACID [VANDF]
Common Name English
68618
Code English
(4E)-6-(4-HYDROXY-6-METHOXY-7-METHYL-3-OXO-1,3-DIHYDRO-2-BENZOFURAN-5-YL)-4-METHYLHEX-4-ENOIC ACID
Systematic Name English
(E)-6-(4-HYDROXY-6-METHOXY-7-METHYL-3-OXO-5-PHTHALANYL)-4-METHYL-4-HEXENOIC ACID
Common Name English
MYCOPHENOLIC ACID [INN]
Common Name English
MYCOPHENOLIC ACID [MI]
Common Name English
4-HEXENOIC ACID, 6-(1,3-DIHYDRO-4-HYDROXY-6-METHOXY-7-METHYL-3-OXO-5-ISOBENZOFURANYL)-4-METHYL-, (4E)-
Common Name English
MYCOPHENOLIC ACID [ORANGE BOOK]
Common Name English
MYCOPHENOLATE MOFETIL IMPURITY, MYCOPHENOLIC ACID- [USP]
Common Name English
MYFORTIC
Brand Name English
MYCOPHENOLIC ACID [USAN]
Common Name English
MYCOPHENOLIC ACID [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 656
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
NDF-RT N0000175613
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
NCI_THESAURUS C2087
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
WHO-ATC L04AA06
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
NCI_THESAURUS C574
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
WHO-VATC QL04AA06
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
Code System Code Type Description
DRUG BANK
DB01024
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
EVMPD
SUB09098MIG
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
246-119-3
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
DRUG CENTRAL
1860
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
MESH
D009173
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
CAS
24280-93-1
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
IUPHAR
6832
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
PUBCHEM
446541
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
LACTMED
Mycophenolate
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
MERCK INDEX
M7682
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY Merck Index
FDA UNII
HU9DX48N0T
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL866
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
RXCUI
265323
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
ALTERNATIVE
EPA CompTox
24280-93-1
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
INN
2950
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
NCI_THESAURUS
C673
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
RXCUI
7145
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY
WIKIPEDIA
MYCOPHENOLIC ACID
Created by admin on Sat Jun 26 11:43:57 UTC 2021 , Edited by admin on Sat Jun 26 11:43:57 UTC 2021
PRIMARY