Identification

Name
Mycophenolic acid
Accession Number
DB01024  (APRD01603, EXPT02208)
Type
Small Molecule
Groups
Approved
Description

Mycophenolic acid is an an immunosuppresant drug and potent anti-proliferative, and can be used in place of the older anti-proliferative azathioprine. It is usually used as part of triple therapy including a calcineurin inhibitor (ciclosporin or tacrolimus) and prednisolone. It is also useful in research for the selection of animal cells that express the E. coli gene coding for XGPRT (xanthine guanine phosphoribosyltransferase).

Structure
Thumb
Synonyms
  • (e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
  • Acide mycophenolique
  • Acido micofenolico
  • Acidum mycophenolicum
  • Micofenolico acido
  • Mycophenolate
  • Mycophenolic acid
  • Mycophenolsäure
External IDs
68618 / NSC-129185
Product Ingredients
IngredientUNIICASInChI Key
Mycophenolate sodiumWX877SQI1G37415-62-6DOZYTHNHLLSNIK-JOKMOOFLSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MyforticTablet, delayed release180 mgOralNovartis2005-02-11Not applicableCanada
MyforticTablet, delayed release180 mg/1OralNovartis Pharmaceuticals Corporation2004-02-27Not applicableUs
MyforticTablet, delayed release180 mg/1OralAvera McKennan Hospital2015-03-012018-05-21Us
MyforticTablet, delayed release360 mgOralNovartis2005-02-11Not applicableCanada
MyforticTablet, delayed release360 mg/1OralNovartis Pharmaceuticals Corporation2004-02-27Not applicableUs00078 0386 66 nlmimage10 a116d0a6
Sandoz Mycophenolic AcidTablet, delayed release180 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
Sandoz Mycophenolic AcidTablet, delayed release360 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-mycophenolic AcidTablet, delayed release180 mgOralApotex Corporation2014-07-02Not applicableCanada
Apo-mycophenolic AcidTablet, delayed release360 mgOralApotex Corporation2014-07-02Not applicableCanada
Mycophenolic AcidTablet, delayed release180 mg/1OralApotex Corp2012-08-21Not applicableUs
Mycophenolic AcidTablet, delayed release180 mg/1OralMylan Institutional2014-01-20Not applicableUs
Mycophenolic AcidTablet, delayed release180 mg/1OralMylan Pharmaceuticals2014-01-08Not applicableUs
Mycophenolic AcidTablet, delayed release180 mg/1OralAccord Healthcare Limited2017-09-11Not applicableUs
Mycophenolic AcidTablet, delayed release180 mg/1OralGolden State Medical Supply, Inc.2014-10-13Not applicableUs
Mycophenolic AcidTablet, delayed release180 mg/1OralAmerincan Health Packaging2015-02-02Not applicableUs
Mycophenolic AcidTablet, delayed release360 mg/1OralApotex Corp2014-08-19Not applicableUs60505 296620180913 8702 1adfsjr
Mycophenolic AcidTablet, delayed release360 mg/1OralMylan Institutional2014-01-20Not applicableUs
International/Other Brands
Melbex
Categories
UNII
HU9DX48N0T
CAS number
24280-93-1
Weight
Average: 320.3371
Monoisotopic: 320.125988372
Chemical Formula
C17H20O6
InChI Key
HPNSFSBZBAHARI-RUDMXATFSA-N
InChI
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+
IUPAC Name
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
SMILES
COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C

Pharmacology

Indication

For the prophylaxis of organ rejection in patients receiving allogeneic renal transplants, administered in combination with cyclosporine and corticosteroids.

Associated Conditions
Pharmacodynamics

Mycophenolic acid is an antibiotic substance derived from Penicillium stoloniferum. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase. Mycophenolic acid is important because of its selective effects on the immune system. It prevents the proliferation of T-cells, lymphocytes, and the formation of antibodies from B-cells. It also may inhibit recruitment of leukocytes to inflammatory sites.

Mechanism of action

Mycophenolic acid is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, mycophenolic acid has potent cytostatic effects on lymphocytes. Mycophenolic acid inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of mycophenolic acid on lymphocytes. Mycophenolic acid also suppresses antibody formation by B-lymphocytes. Mycophenolic acid prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection.

TargetActionsOrganism
AInosine-5'-monophosphate dehydrogenase 1
inhibitor
Human
AInosine-5'-monophosphate dehydrogenase 2
inhibitor
Human
Absorption

Bioavailability following oral administration of Myfortic delayed-release tablet ranges from 70-95%

Volume of distribution
  • 54 ± 25 L
Protein binding

>98%

Metabolism

Mycophenolic acid is metabolized mainly by glucuronyl transferase to glucuronidated metabolites, predominantly the phenolic glucuronide, mycophenolic acid glucuronide (MPAG). MPAG does not manifest pharmacological activity. The acyl glucuronide minor metabolite has pharmacological activity similar to mycophenolic acid. The AUC ratio of Mycophenolic acid:MPAG:acyl glucuronide is approximately 1:24:0.28 at steady state.

Route of elimination
Not Available
Half life

The mean elimination half-life for mycophenolic acid ranges from 8-16 hours, while that of the MPAG metabolite ranges from 13-17 hours.

Clearance
  • 140 +/- 30 mL/min [Stable renal transplant patients]
Toxicity

Oral (LD50): Acute: 352 mg/kg [Rat], 1000 mg/kg [Mouse], and >6000 mg/kg Rabbit. Possible signs and symptoms of acute overdose could include the following: hematological abnormalities such as leukopenia and neutropenia, and gastrointestinal symptoms such as abdominal pain, diarrhea, nausea and vomiting, and dyspepsia.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Mycophenolic Acid Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with 2-Methoxyethanol.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
AbacavirMycophenolic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Abatacept.
AbetimusThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Abetimus.
AcarboseAcarbose may decrease the excretion rate of Mycophenolic acid which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Mycophenolic acid which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Mycophenolic acid which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Mycophenolic acid which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Mycophenolic acid which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
Not Available

References

Synthesis Reference

Bernard J. Abbott, John G. Whitney, "Method of preparing mycophenolic acid glucoside." U.S. Patent US4234684, issued January, 1976.

US4234684
General References
  1. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv. [PubMed:15899149]
External Links
Human Metabolome Database
HMDB0015159
PubChem Compound
446541
PubChem Substance
46504559
ChemSpider
393865
BindingDB
19264
ChEBI
168396
ChEMBL
CHEMBL866
Therapeutic Targets Database
DAP000784
PharmGKB
PA164748728
HET
MOA
Drugs.com
Drugs.com Drug Page
Wikipedia
Mycophenolic_acid
ATC Codes
L04AA06 — Mycophenolic acid
AHFS Codes
  • 92:44.00 — Immunosuppressive Agents
PDB Entries
1jr1 / 1me7 / 1meh / 1mei / 4af0 / 4fo4 / 4fxs
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentAllogeneic peripheral haematopoietic stem cell transplant / Neuroepithelial Tumor / Tumors, Solid1
0WithdrawnTreatmentMultiple Myeloma (MM) / Myeloma-Multiple1
1CompletedTreatmentDrug Interaction Potentiation1
1CompletedTreatmentEnd Stage Renal Disease (ESRD) / Transplantation, Kidney1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentPrimary Sjogren's Syndrome1
1RecruitingTreatmentAgnogenic Myeloid Metaplasia / Leukemias / Malignant Lymphomas / Smith-Magenis Syndrome1
1RecruitingTreatmentHaemoglobinopathies congenital / Sickle Cell Disorders / Thalassaemic disorders1
1RecruitingTreatmentRenal Transplant Recipient Patients / Transplantation, Kidney / Transplantation, Renal1
1RecruitingTreatmentTransplantation, Liver1
1, 2CompletedBasic ScienceTransplantation, Kidney1
1, 2CompletedTreatmentDiabetes, Diabetes Mellitus Type 11
1, 2CompletedTreatmentGraft Versus Host Disease (GVHD) / Malignancies, Hematologic1
1, 2CompletedTreatmentMalignancies, Hematologic1
1, 2CompletedTreatmentScleroderma, Systemic / Severe Systemic Sclerosis1
1, 2CompletedTreatmentTransplantation, Kidney1
1, 2RecruitingTreatmentAdult Living Donor Kidney Transplant Recipients / Living Kidney Donors / Transplant, Kidney1
1, 2Unknown StatusTreatmentHematologic Diseases1
2Active Not RecruitingPreventionGraft Versus Host Disease (GVHD)1
2Active Not RecruitingTreatmentCrohn's Disease (CD)1
2Active Not RecruitingTreatmentLeukemias / Malignant Lymphomas1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
2CompletedTreatmentNephritis, Lupus1
2CompletedTreatmentTransplantation, Renal1
2Not Yet RecruitingTreatmentAntibody-mediated Rejection / Lung Transplant Rejection1
2RecruitingTreatmentAccelerated Phase Chronic Myelogenous Leukemia / Adult Acute Lymphoblastic Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Blastic Phase Chronic Myelogenous Leukemia / Childhood Acute Lymphoblastic Leukemia in Remission / Childhood Burkitt Lymphoma / Childhood Chronic Myelogenous Leukemia / Childhood Diffuse Large Cell Lymphoma / Childhood Immunoblastic Large Cell Lymphoma / Childhood Myelodysplastic Syndromes / Childhood Nasal Type Extranodal NK/T-cell Lymphoma / Chronic Myelomonocytic Leukemia / Chronic Phase Chronic Myelogenous Leukemia / Cutaneous B-Cell Non-Hodgkin Lymphoma / De Novo Myelodysplastic Syndromes / Essential Thrombocythemia (ET) / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Hepatosplenic T-Cell Lymphoma / Intraocular Lymphoma / Juvenile Myelomonocytic Leukemia / Nodal marginal zone B-cell lymphomas / Noncutaneous Extranodal Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Polycythemia Vera (PV) / Post Transplant Lymphoproliferative Disorder / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Recurrent Adult Acute Myeloid Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Childhood Acute Myeloid Leukemia / Recurrent Childhood Anaplastic Large Cell Lymphoma / Recurrent Childhood Grade III Lymphomatoid Granulomatosis / Recurrent Childhood Large Cell Lymphoma / Recurrent Childhood Lymphoblastic Lymphoma / Recurrent Childhood Small Noncleaved Cell Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Recurrent/Refractory Childhood Hodgkin Lymphoma / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation / Refractory Cytopenia With Multilineage Dysplasia / Refractory Hairy Cell Leukemia / Refractory Multiple Myeloma / Relapsing Chronic Myelogenous Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Small Intestine Lymphoma / Splenic Marginal Zone Lymphoma / T-Cell Large Granular Lymphocyte Leukemia / Testicular Lymphoma / Waldenström's Macroglobulinemia (WM)1
2RecruitingTreatmentAcute myeloid leukaemia (in remission) / Aplastic Anaemia (AA) / Chronic Myelomonocytic Leukemia / Indolent Non-Hodgkin's Lymphomas / Leukemia Acute Myeloid Leukemia (AML) / Lymphoma, Hodgkins / Myelodysplastic Syndrome / Myeloproliferative Neoplasms / Neoplasms, Malignant / Plasma Cell Myeloma / Refractory Anemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Ring Sideroblasts / Refractory Cytopenia With Multilineage Dysplasia / Refractory Cytopenia With Multilineage Dysplasia and Ring Sideroblasts1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentNon-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Myelogenous Leukaemia (AML) / All / Chronic Lymphocytic Leukaemia (CLL) / Leukemia Acute Myeloid Leukemia (AML) / Leukemias / Lymphoma, Hodgkins / Malignancies, Hematologic / Malignant Lymphomas / Non-Hodgkin's Lymphoma (NHL) / Plasma Cell Myeloma1
2TerminatedTreatmentLeukemias / Myelodysplastic Syndromes1
2TerminatedTreatmentMalignant Lymphomas1
2TerminatedTreatmentNeoplasms, Malignant1
2Unknown StatusTreatmentRenal Insufficiency,Chronic / Transplantation, Liver1
2WithdrawnTreatmentDiabetes, Diabetes Mellitus Type 11
2, 3RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
3Active Not RecruitingTreatmentUveitis, Intermediate1
3CompletedPreventionTransplantation, Kidney1
3CompletedTreatmentAutoimmune Diseases1
3CompletedTreatmentGlomerulonephritis minimal lesion1
3CompletedTreatmentKidney Diseases1
3CompletedTreatmentLymphoma, Hodgkins / Non-Hodgkin's Lymphoma (NHL)1
3CompletedTreatmentPancreas Transplantation / Transplantation, Kidney1
3CompletedTreatmentRejection, Transplant / Transplantation, Kidney1
3CompletedTreatmentRenal Interstitial Fibrosis1
3CompletedTreatmentTransplant, Kidney4
3CompletedTreatmentTransplant; Failure, Kidney1
3CompletedTreatmentTransplantation, Kidney2
3CompletedTreatmentTransplantation, Liver3
3CompletedTreatmentTransplantation, Renal3
3RecruitingTreatmentChronic Kidney Disease (CKD)1
3TerminatedNot AvailableSarcoidosis, Pulmonary1
3TerminatedTreatmentGraft Versus Host Disease (GVHD)1
3TerminatedTreatmentNephritis, Lupus1
3TerminatedTreatmentSystemic Lupus Erythematosus (SLE)1
3Unknown StatusTreatmentHeart Transplant Patients1
4Active Not RecruitingPreventionInfections, Cytomegalovirus / Transplantation Infection1
4Active Not RecruitingTreatmentCytomegalovirus / Transplantation, Kidney1
4Active Not RecruitingTreatmentKidney Transplant Rejection / Other Complications of Kidney Transplant1
4Active Not RecruitingTreatmentTransplantation, Renal1
4CompletedPreventionAdverse Effects / Transplantation, Kidney1
4CompletedPreventionHepatitis C Viral Infection1
4CompletedPreventionTransplantation, Kidney1
4CompletedSupportive CareTransplantation, Renal1
4CompletedTreatmentBK Virus Infection1
4CompletedTreatmentBioavailability / Concomitant Medication After Renal Transplantation / Drug Drug Interaction (DDI) / Immunosuppressive Medication After Renal Transplantation1
4CompletedTreatmentChronic Kidney Disease (CKD) / End Stage Renal Disease (ESRD) / Hemodialysis Treatment / Renal Replacement Therapies / Transplantation, Renal1
4CompletedTreatmentChronic Renal Failure (CRF)1
4CompletedTreatmentDisorder Related to Renal Transplantation / Infections, Cytomegalovirus1
4CompletedTreatmentEnd Stage Renal Disease (ESRD)1
4CompletedTreatmentEnd-Stage Renal Disease (ESRD)1
4CompletedTreatmentGastrointestinal Lesions / Signs and Symptoms, Digestive1
4CompletedTreatmentGastrointestinal Problems / Transplantation, Renal1
4CompletedTreatmentGastrointestinal Symptoms / Heart Transplantation1
4CompletedTreatmentGlomerulonephritis minimal lesion1
4CompletedTreatmentHeart Transplantation1
4CompletedTreatmentImplant or Graft; Rejection1
4CompletedTreatmentInfections, Cytomegalovirus / Renal Transplant Failure / Transplant; Complication, Rejection1
4CompletedTreatmentInfections, Cytomegalovirus / Transplantation Infection1
4CompletedTreatmentLiver Cirrhosis / Liver Transplant Disorder1
4CompletedTreatmentRenal Function1
4CompletedTreatmentRenal Transplant Recipient Patients2
4CompletedTreatmentTransplant, Kidney2
4CompletedTreatmentTransplant, Kidney / Transplantation, Kidney1
4CompletedTreatmentTransplantation, Kidney2
4CompletedTreatmentTransplantation, Liver1
4CompletedTreatmentTransplantation, Renal3
4Not Yet RecruitingTreatmentImmunosuppression After Renal Transplantation / Transplant, Kidney1
4RecruitingPreventionInfections, Cytomegalovirus1
4RecruitingPreventionKidney Transplant Infection1
4RecruitingTreatmentAntibody Mediated Rejection / End Stage Renal Disease (ESRD)1
4RecruitingTreatmentChronic Renal Failure (CRF) / Graft Failure / Kidney Transplant Rejection / Transplant; Failure, Kidney1
4RecruitingTreatmentGastrointestinal Disorder, Functional / Kidney Transplant Rejection1
4RecruitingTreatmentHepatocellular,Carcinoma1
4RecruitingTreatmentImmunosuppression1
4TerminatedPreventionSkin Cancers / Transplantation, Kidney1
4TerminatedPreventionTransplantation, Kidney1
4TerminatedPreventionTransplantation, Renal1
4TerminatedTreatmentTransplantation, Kidney / Transplants and Implants1
4TerminatedTreatmentTransplantation, Renal2
4Unknown StatusPreventionDiabetes Mellitus (DM) / Rejection, Transplant1
4Unknown StatusPreventionKidney; Complications, Allograft1
4Unknown StatusTreatmentInfections, Cytomegalovirus1
4Unknown StatusTreatmentTransplant, Kidney1
4Unknown StatusTreatmentTransplantation, Organ1
4Unknown StatusTreatmentTransplantation, Renal1
4WithdrawnTreatmentCardiovascular Disease (CVD) / Cardiovascular Outcomes / Renal Transplant Recipient Patients / Transplantation, Kidney1
4WithdrawnTreatmentLiving Donor Kidney Transplants Patients1
4WithdrawnTreatmentReperfusion Injury / Transplantation, Kidney / Transplantation, Renal1
4WithdrawnTreatmentTransplantation, Liver1
Not AvailableActive Not RecruitingPreventionImmunosuppression / Renal Failure1
Not AvailableCompletedNot AvailableDiabetes, Diabetes Mellitus Type 1 / Islet Transplantation1
Not AvailableCompletedNot AvailableEnd Stage Liver Diseases1
Not AvailableCompletedNot AvailableGI Disturbance1
Not AvailableCompletedTreatmentArthritis / Systemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentHigh Model for End-Stage Liver Disease (MELD) Score1
Not AvailableCompletedTreatmentImmunosuppression2
Not AvailableEnrolling by InvitationNot AvailableGastrointestinal Complications / Sclerosis, Progressive Systemic1
Not AvailableNo Longer AvailableNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableNot Yet RecruitingNot AvailableAcute Rejection of Renal Transplant / Biopsy Proven Acute Rejection (BPAR) / Bone Diseases / Cardiovascular Risk Factors / Graft Failure / HLA Antibody Production / Infection NOS / Non-HLA Antibody Production / Post Transplant Diabetes Mellitus / Quality of Life / The Mortality Rate1
Not AvailableRecruitingNot AvailableNephritis, Lupus1
Not AvailableRecruitingPreventionDiabetes, Diabetes Mellitus Type 11
Not AvailableRecruitingTreatmentDisorder Related to Renal Transplantation / Effects of Immunosuppressant Therapy1
Not AvailableTerminatedTreatmentAcute Rejection / Transplantation, Renal1
Not AvailableTerminatedTreatmentCalcineurin Inhibitor Toxicity / Chronic Allograft Injury1
Not AvailableTerminatedTreatmentTransplantation, Kidney1
Not AvailableTerminatedTreatmentTransplantation, Liver1
Not AvailableUnknown StatusNot AvailableUveitis1
Not AvailableUnknown StatusTreatmentMyasthenia Gravis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Novartis AG
Dosage forms
FormRouteStrength
Tablet, delayed releaseOral180 mg
Tablet, delayed releaseOral360 mg
Tablet, delayed releaseOral360 mg/1
Tablet, delayed releaseOral180 mg/1
Prices
Unit descriptionCostUnit
Myfortic 360 mg Enteric Coated Tabs8.0USD tab
Myfortic 360 mg tablet7.69USD tablet
Myfortic 180 mg tablet3.85USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2250906No2006-10-032017-04-10Canada
US6025391No2000-02-152017-04-10Us
US6172107No2001-01-092017-04-10Us
US6306900No2001-10-232018-02-27Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)141 °CPhysProp
water solubilityInsolubleNot Available
logP2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0355 mg/mLALOGPS
logP2.36ALOGPS
logP3.53ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.23 m3·mol-1ChemAxon
Polarizability32.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9409
Blood Brain Barrier+0.5826
Caco-2 permeable-0.5583
P-glycoprotein substrateSubstrate0.8058
P-glycoprotein inhibitor INon-inhibitor0.7888
P-glycoprotein inhibitor IIInhibitor0.545
Renal organic cation transporterNon-inhibitor0.8199
CYP450 2C9 substrateNon-substrate0.8305
CYP450 2D6 substrateNon-substrate0.8575
CYP450 3A4 substrateSubstrate0.6934
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7237
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9619
BiodegradationReady biodegradable0.5888
Rat acute toxicity2.9907 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.753
hERG inhibition (predictor II)Non-inhibitor0.6329
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-002r-0490000000-99420edc8894323b59c3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-b99d88ff2ddeb6977c4a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0149000000-ed6b854b4f9af495c8d8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0972000000-12d0e80f109d1fa6eb11
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0950000000-2e6c3543fe3f9f4e0790
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0930000000-e7a74fbe76e7141ec5f3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-022c-0910000000-27f7c0023a8b7e5b4d66
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-4aba5ee4ba77899b36fb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0149000000-497b49ab395f3319c943
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0971000000-68634f04b665bb0e68a3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0950000000-37f2ee0320d2ec560b93
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0f6x-0930000000-500359a3fd82c686ff99
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-006x-0900000000-6d04c3395aae26f88529
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-002r-0590000000-fe2f27357ba775714c5a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-8f75c9bc48b5eb019974
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-57a06531623d00c32d13
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-002r-0490000000-700501110e03f998e99b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-002r-0490000000-d857a6e047fc52e09e65
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0659000000-ba96d820001d9e786c8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0009000000-8855932a0a5c9af1f1f6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0009000000-5eab5855829b8f8b0eea
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-0093000000-19fd59af4878ea5f1a97
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-6f584505d9b70bbffa5e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0890000000-fb7dec2fc3d23163125f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-107f1e78387f32f7de88
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pbc-3900000000-b1724166cac37a86cf14
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0009000000-8de82df3dfe7724905cc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-0093000000-921ff4437b7ebfa1c724
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-51bdcbf497148c8b5520
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0890000000-c295a83b84c00d94f85f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-92e91c6ef0f2c538121f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pbc-3900000000-410eebeb0513756f40b0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0009000000-77bcd201c9d0349c0389
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-da3123e3ecb85f0d28ff
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-90103d288430929083b5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0090000000-3f6f29caf26c0469c12c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0090000000-7fc1bdce2eebcc00617c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0019000000-01d925bb1f9079308d85
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0091000000-22fc916594dbab851293
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0940000000-84f4c65c2cd8b7358b78
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0593000000-1fed07ad435ca0bd7249
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0950000000-87024d6b180d1fc1c64f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0493000000-9b99fb030e87f52cce17
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0294000000-31d6abb5cfcd65770f2c

Taxonomy

Description
This compound belongs to the class of organic compounds known as phthalides. These are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isocoumarans
Sub Class
Isobenzofuranones
Direct Parent
Phthalides
Alternative Parents
Anisoles / Medium-chain fatty acids / Alkyl aryl ethers / Methyl-branched fatty acids / Hydroxy fatty acids / Heterocyclic fatty acids / Unsaturated fatty acids / Dicarboxylic acids and derivatives / Vinylogous acids / Lactones
show 6 more
Substituents
Phthalide / Anisole / Medium-chain fatty acid / Alkyl aryl ether / Branched fatty acid / Methyl-branched fatty acid / Heterocyclic fatty acid / Hydroxy fatty acid / Dicarboxylic acid or derivatives / Fatty acyl
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
2-benzofurans, monocarboxylic acid, phenols, gamma-lactone (CHEBI:168396)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH1
Uniprot ID
P20839
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 1
Molecular Weight
55405.365 Da
References
  1. Dzidic A, Prgomet C, Mohr A, Meyer K, Bauer J, Meyer HH, Pfaffl MW: Effects of mycophenolic acid on inosine monophosphate dehydrogenase I and II mRNA expression in white blood cells and various tissues in sheep. J Vet Med A Physiol Pathol Clin Med. 2006 May;53(4):163-9. [PubMed:16629948]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH2
Uniprot ID
P12268
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 2
Molecular Weight
55804.495 Da
References
  1. Vannozzi F, Filipponi F, Di Paolo A, Danesi R, Urbani L, Bocci G, Catalano G, De Simone P, Mosca F, Del Tacca M: An exploratory study on pharmacogenetics of inosine-monophosphate dehydrogenase II in peripheral mononuclear cells from liver-transplant recipients. Transplant Proc. 2004 Nov;36(9):2787-90. [PubMed:15621150]
  2. Wang J, Zeevi A, Webber S, Girnita DM, Addonizio L, Selby R, Hutchinson IV, Burckart GJ: A novel variant L263F in human inosine 5'-monophosphate dehydrogenase 2 is associated with diminished enzyme activity. Pharmacogenet Genomics. 2007 Apr;17(4):283-90. [PubMed:17496727]
  3. Penuelas S, Noe V, Morales R, Ciudad CJ: Sensitization of human erythroleukemia K562 cells resistant to methotrexate by inhibiting IMPDH. Med Sci Monit. 2005 Jan;11(1):BR6-12. [PubMed:15614187]
  4. Yam P, Jensen M, Akkina R, Anderson J, Villacres MC, Wu J, Zaia JA, Yee JK: Ex vivo selection and expansion of cells based on expression of a mutated inosine monophosphate dehydrogenase 2 after HIV vector transduction: effects on lymphocytes, monocytes, and CD34+ stem cells. Mol Ther. 2006 Aug;14(2):236-44. Epub 2006 May 2. [PubMed:16647299]
  5. Dzidic A, Prgomet C, Mohr A, Meyer K, Bauer J, Meyer HH, Pfaffl MW: Effects of mycophenolic acid on inosine monophosphate dehydrogenase I and II mRNA expression in white blood cells and various tissues in sheep. J Vet Med A Physiol Pathol Clin Med. 2006 May;53(4):163-9. [PubMed:16629948]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165]
  2. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165]
  2. Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165]
  2. Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A7
Uniprot ID
Q9HAW7
Uniprot Name
UDP-glucuronosyltransferase 1-7
Molecular Weight
59818.315 Da
References
  1. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 17:08