MYCOPHENOLIC ACID

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

Structure Search

SMILES

COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C

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

Molecular Formula	C17H20O6
Molecular Weight	320.3371
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050791s024lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27903231

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Inosine-5'-monophosphate dehydrogenase (IMPDH) 11 Target ID: CHEMBL2111369 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15803924 \| https://www.ncbi.nlm.nih.gov/pubmed/10878285	Inhibitor 8504
Inosine-5'-monophosphate dehydrogenase (IMPDH) 11 Target ID: CHEMBL2111369 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11880114	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Organ transplant rejection 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050791s024lbl.pdf	Preventing		Approved 8583	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 2004

C_max

Value	Dose	Co-administered	Analyte	Population
18.9 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050791s019lbl.pdf	720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered: CYCLOSPORINE	CYCLOSPORINE	MYCOPHENOLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
57.4 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050791s019lbl.pdf	720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered: CYCLOSPORINE	CYCLOSPORINE	MYCOPHENOLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.7 h DRUG LABEL https://www.novartis.com.sg/system/files/product-info/MYFORTIC%20PI%20Nov2013.SINv1_.pdf	720 mg 2 times / day multiple, oral dose: 720 mg route of administration: Oral experiment type: MULTIPLE co-administered:		MYCOPHENOLIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A4/5 296	CYP3A4/5 91 P-gp 2052 UGT 219 CYP2C8 810 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C18 149 CYP2C19 1119 CYP2E1 729 CYP3A7 109 UGT1A9 423 UGT1A1 479 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT1A3 470 UGT1A4 399

Drug as perpetrator

Target	Modality	Activity
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=21 Page: 21.0	weak [Ki 57 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=6 Page: 6.0	weak [Ki 98 uM]

Drug as victim

Target	Modality	Activity
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	likely
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=5 Page: 5.0	major
CYP3A4/5 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	minor
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
CYP3A7 109	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15570183/ Page: -	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-791_Myfortic_biopharmr.PDF#page=22 Page: 22.0	no
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	no
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes [Km 1390 uM]
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes [Km 160 uM]
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes [Km 200 uM]
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes [Km 410 uM]
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes [Km 480 uM]
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15470161/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:168396	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:168396
ChemicalBook	CB4507365	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4507365
ChemicalBook	CB8311003	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8311003
eMolecules	18595868	https://www.emolecules.com/cgi-bin/more?vid=18595868
MolPort	MolPort-001-732-316	https://www.molport.com/shop/molecule-link/MolPort-001-732-316
Selleck Chemicals	Mycophenolic-acid(Mycophenolate)	http://www.selleckchem.com/products/Mycophenolic-acid(Mycophenolate).html
ZINC	ZINC000000001758	http://zinc15.docking.org/substances/ZINC000000001758

PubMed

Title	Date	PubMed
Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function.	2015-12-25	26394380
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Characterization of the zebrafish Ugt repertoire reveals a new class of drug-metabolizing UDP glucuronosyltransferases.	2014-07	24728488
Transcriptome-based functional classifiers for direct immunotoxicity.	2014-03	24356939
Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines.	2013-11	23999140
Effects of mycophenolic acid alone and in combination with its metabolite mycophenolic acid glucuronide on rat embryos in vitro.	2013-02	22914985
Intracellular GTP level determines cell's fate toward differentiation and apoptosis.	2011-06-15	21396949
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.	2011-02	20736080
Mycophenolic acid in rheumatology: mechanisms of action and severe adverse events.	2010-07-27	20657885
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.	2010-05-14	20302854
Inflammation-associated gene transcription and expression in mouse lungs induced by low molecular weight compounds from fungi from the built environment.	2010-01-05	19818335
Antiviral activity of indole derivatives.	2009-08	19445965
Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives.	2009-07-01	19482481
[Wegener's granulomatosis and microscopic polyangiitis].	2009-02	19184066
The necrotic signal induced by mycophenolic acid overcomes apoptosis-resistance in tumor cells.	2009	19430526
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.	2008-11	17950325
Effect of D256N and Y483D on propofol glucuronidation by human uridine 5'-diphosphate glucuronosyltransferase (UGT1A9).	2008-08	18816295
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.	2008-04	18498916
Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells.	2007-06	17463174
Conversion from mycophenolate mofetil to enteric-coated mycophenolate sodium in maintenance renal transplant recipients receiving tacrolimus: clinical, pharmacokinetic, and pharmacodynamic outcomes.	2007-02-27	17318074
Mycophenolic acid induces islet apoptosis by regulating mitogen-activated protein kinase activation.	2006-12	17175248
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.	2006-07-26	16930453
Mycophenolic acid inhibits syncytium formation accompanied by reduction of gp120 expression.	2005-08	16266123
[Mycophenolic acid induced apoptosis in T lymphocytic cells Molt-4 and its mechanism].	2005-07	16059982
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study.	2005-05	15899149
Synergy between imatinib and mycophenolic acid in inducing apoptosis in cell lines expressing Bcr-Abl.	2005-04-15	15604220
Mechanisms of action of mycophenolate mofetil.	2005	15803924
Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5.	2004-12	15570183
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.	2004-11	15504868
Mycophenolic acid inhibits avian reovirus replication.	2004-10	15451179
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.	2003-08	12730611
Anti-HIV-1 activity of leflunomide: a comparison with mycophenolic acid and hydroxyurea.	2003-07-25	12853743
Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus.	2003-06-14	12814717
The effect of ribavirin and IMPDH inhibitors on hepatitis C virus subgenomic replicon RNA.	2003-06-05	12781720
Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents.	2002-11	12718406
Mycophenolic acid inhibits IL-2-dependent T cell proliferation, but not IL-2-dependent survival and sensitization to apoptosis.	2002-09-01	12193749
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002-07	12076755
Dose proportional inhibition of HIV-1 replication by mycophenolic acid and synergistic inhibition in combination with abacavir, didanosine, and tenofovir.	2002-07	12076750
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.	2002-05-23	12014950
Characterization of wild-type and cidofovir-resistant strains of camelpox, cowpox, monkeypox, and vaccinia viruses.	2002-05	11959564
Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.	2001-11	12018677
Mycophenolate mofetil treatment accelerates recovery from experimental allergic encephalomyelitis.	2001-09	11562063
Inosine-5'-monophosphate dehydrogenase is required for mitogenic competence of transformed pancreatic beta cells.	2001-01	11145582
Mycophenolate mofetil and its mechanisms of action.	2000-05	10878285
The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair.	2000-03	10688038
Abacavir and mycophenolic acid, an inhibitor of inosine monophosphate dehydrogenase, have profound and synergistic anti-HIV activity.	1999-08-15	10458616
Novel mycophenolic adenine bis(phosphonate)s as potential immunosuppressants.	1999-07	10390605
Polymerase substrate depletion: a novel strategy for inhibiting the replication of the human immunodeficiency virus.	1995-08-20	7544050
Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid.	1990-02	1967654

Patents

Sample Use Guides

In Vivo Use Guide

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

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:17 GMT 2025`
Record UNII	HU9DX48N0T
Record Status	`Validated (UNII)`
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Name

Type

Language

MYCOPHENOLATE

Preferred Name

English

MYCOPHENOLIC ACID

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

MYCOPHENOLIC ACID [MART.]

Common Name

English

NSC-129185

Code

English

MYCOPHENOLATE MOFETIL IMPURITY F [EP IMPURITY]

Common Name

English

MYCOPHENOLIC ACID [VANDF]

Common Name

English

68618

Code

English

Mycophenolic acid [WHO-DD]

Common Name

English

MYCOPHENOLATE MOFETIL IMPURITY, MYCOPHENOLIC ACID- [USP IMPURITY]

Common Name

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

MYFORTIC

Brand Name

English

MYCOPHENOLIC ACID [USAN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548945