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Identification
NameMycophenolate mofetil
Accession NumberDB00688  (APRD01602)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Mycophenolate mofetil is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent, inosine monophosphate dehydrogenase (IMPDH) inhibitor.

Structure
Thumb
Synonyms
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate
Cellcept
MMF
Mycophenolic acid morpholinoethyl ester
RS 61443
External Identifiers
  • 168396
  • RS 61443
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-mycophenolate Mofetil Capsulescapsule250 mgoralAccel Pharma IncNot applicableNot applicableCanada
Accel-mycophenolate Mofetil Tabletstablet500 mgoralAccel Pharma IncNot applicableNot applicableCanada
Ach-mycophenolatecapsule250 mgoralAccord Healthcare Inc2012-05-01Not applicableCanada
Cellceptcapsule250 mg/1oralGenentech, Inc.1995-05-03Not applicableUs
Cellcepttablet, film coated500 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1997-06-19Not applicableUs
Cellceptcapsule250 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-29Not applicableUs
Cellceptpowder for suspension200 mgoralHoffmann La Roche Limited2002-08-27Not applicableCanada
Cellceptcapsule250 mg/1oralRebel Distributors Corp1995-05-03Not applicableUs
Cellceptinjection, powder, lyophilized, for solution500 mg/20mLintravenousGenentech, Inc.1998-08-12Not applicableUs
Cellcepttablet500 mgoralHoffmann La Roche Limited1998-11-11Not applicableCanada
Cellceptpowder, for suspension200 mg/mLoralGenentech, Inc.1998-10-01Not applicableUs
Cellceptcapsule250 mgoralHoffmann La Roche Limited1995-12-31Not applicableCanada
Cellcepttablet, film coated500 mg/1oralGenentech, Inc.1997-06-19Not applicableUs
Cellceptcapsule250 mg/1oralCardinal Health1995-05-03Not applicableUs
Cellcept I.V.powder for solution500 mgintravenousHoffmann La Roche Limited1999-12-20Not applicableCanada
Co Mycophenolatetablet500 mgoralCobalt Pharmaceuticals Company2012-02-14Not applicableCanada
Jamp-mycophenolatetablet500 mgoralJamp Pharma Corporation2012-03-23Not applicableCanada
Jamp-mycophenolate Capsulescapsule250 mgoralJamp Pharma Corporation2012-06-13Not applicableCanada
Mycophenolate Mofetil for Injection, USPpowder for solution500 mgintravenousAccord Healthcare IncNot applicableNot applicableCanada
Mycophenolate Mofetil Tabletstablet500 mgoralAccord Healthcare Inc2012-02-16Not applicableCanada
Mylan-mycophenolatecapsule250 mgoralMylan Pharmaceuticals Ulc2011-11-30Not applicableCanada
Mylan-mycophenolatetablet500 mgoralMylan Pharmaceuticals Ulc2011-11-30Not applicableCanada
Novo-mycophenolatecapsule250 mgoralTeva Canada Limited2011-11-30Not applicableCanada
Novo-mycophenolatetablet500 mgoralTeva Canada Limited2011-11-30Not applicableCanada
Ran-mycophenolatetablet500 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Sandoz Mycophenolate Mofetilcapsule250 mgoralSandoz Canada Incorporated2011-11-30Not applicableCanada
Sandoz Mycophenolate Mofetiltablet500 mgoralSandoz Canada Incorporated2011-11-30Not applicableCanada
Van-mycophenolatetablet500 mgoralVanc Pharmaceuticals Inc2015-07-22Not applicableCanada
Van-mycophenolatecapsule250 mgoralVanc Pharmaceuticals Inc2015-07-22Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-mycophenolatetablet500 mgoralApotex Inc2011-12-01Not applicableCanada
Apo-mycophenolatecapsule250 mgoralApotex Inc2011-12-01Not applicableCanada
Mycophenolate Mofetilcapsule250 mg/1oralAscend Laboratories, LLC2010-01-01Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralCardinal Health2011-10-25Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralRoxane Laboratories, Inc2008-07-29Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralAmerican Health Packaging2014-12-15Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralJUBILANT CADISTA PHARMACEUTICALS, INC.2013-08-01Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralSandoz Inc2008-10-15Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralQualitest Pharmaceuticals2010-07-192015-12-29Us
Mycophenolate Mofetilcapsule250 mg/1oralApotex Corp2009-05-04Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralCardinal Health2011-10-25Not applicableUs
Mycophenolate Mofetilpowder, for suspension200 mg/mLoralAscend Laboratories, LLC2014-11-17Not applicableUs
Mycophenolate Mofetiltablet, coated500 mg/1oralApotex Corp2009-05-04Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralMylan Pharmaceuticals Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralQualitest Pharmaceuticals2010-03-162015-12-29Us
Mycophenolate Mofetilcapsule250 mg/1oralMylan Institutional Inc.2009-06-01Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralAscend Laboratories, LLC2011-11-28Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralMylan Pharmaceuticals Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralAvera Mc Kennan Hospital2015-03-01Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralGolden State Medical Supply, Inc.2015-01-06Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralMylan Institutional Inc.2009-06-01Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralCadila Healthcare Limited2009-05-04Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2009-05-05Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralZydus Pharmaceuticals (USA) Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralGolden State Medical Supply, Inc.2015-01-06Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralAccord Healthcare Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralCadila Healthcare Limited2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralTeva Pharmaceuticals USA Inc2009-05-06Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralZydus Pharmaceuticals (USA) Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralGreenstone LLC2010-06-11Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralAccord Healthcare Inc.2009-05-04Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralStrides Arcolab Limited2010-11-06Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralJUBILANT CADISTA PHARMACEUTICALS, INC.2013-08-01Not applicableUs
Mycophenolate Mofetilcapsule250 mg/1oralAmerican Health Packaging2012-07-02Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralRoxane Laboratories, Inc2008-07-29Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralAmerican Health Packaging2014-12-15Not applicableUs
Mycophenolate Mofetiltablet, film coated500 mg/1oralGreenstone LLC2010-06-11Not applicableUs
Mycophenolate Mofetiltablet500 mg/1oralSandoz Inc2008-10-15Not applicableUs
Mycophenolate Mofetiltablet, coated500 mg/1oralAmerican Health Packaging2012-07-022015-12-31Us
Mycophenolate Mofetiltablet, film coated500 mg/1oralStrides Arcolab Limited2010-11-06Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CellCept Oral Suspension Genentech USA, Inc.
CellCept IntravenousGenentech USA, Inc.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mycophenolate mofetil hydrochloride
ThumbNot applicableDBSALT001477
Categories
UNII9242ECW6R0
CAS number128794-94-5
WeightAverage: 433.4947
Monoisotopic: 433.210052351
Chemical FormulaC23H31NO7
InChI KeyInChIKey=RTGDFNSFWBGLEC-SYZQJQIISA-N
InChI
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+
IUPAC Name
2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
SMILES
COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phthalides. These are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsobenzofurans
Sub ClassIsobenzofuranones
Direct ParentPhthalides
Alternative Parents
Substituents
  • Phthalide
  • Methoxyphenol
  • Anisole
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxazinane
  • Morpholine
  • Dicarboxylic acid or derivatives
  • Vinylogous acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the prophylaxis of organ rejection in patients receiving allogeneic renal, cardiac or hepatic transplants. Mycophenolate mofetil should be used concomitantly with cyclosporine and corticosteroids.
PharmacodynamicsMycophenolate mofetil is a prodrug of mycophenolic acid (MPA), 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 actionMycophenolate mofetil is hydrolyzed to form mycophenolic acid (MPA), which is the active metabolite. MPA 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, MPA has potent cytostatic effects on lymphocytes. MPA inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of MPA on lymphocytes. MPA also suppresses antibody formation by B-lymphocytes. MPA 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. Mycophenolate mofetil did not inhibit early events in the activation of human peripheral blood mononuclear cells, such as the production of interleukin-1 (IL-1) and interleukin-2 (IL-2), but did block the coupling of these events to DNA synthesis and proliferation.
Related Articles
AbsorptionRapidly absorbed following oral administration. In 12 healthy volunteers, the mean absolute bioavailability of oral mycophenolate mofetil relative to intravenous mycophenolate mofetil (based on MPA AUC) was 94%. The absolute bioavailability of the delayed release tablet in stable renal transplant patients on cyclosporin is 72%. Food (27 g fat, 650 calories) has no effect on the extent of absorption (MPA AUC) of mycophenolate mofetil.
Volume of distribution
  • 3.6 ±1.5 L/kg [intravenous, healthy subjects, MPA]
  • 4 ±1.2 L/kg [oral administration, healthy subjects, MPA]
Protein bindingMPA (the active metabolite), at clinically relevant concentrations, is over 98% bound to plasma albumin. The phenolic glucuronide of MPA, mycophenolic acid glucuronide (MPAG) has 82% protein bound.
Metabolism

Following oral and intravenous dosing, mycophenolate mofetil undergoes complete metabolism to MPA, the active metabolite. Metabolism to MPA occurs presystemically after oral dosing. MPA is metabolized principally by glucuronyl transferase to form the phenolic glucuronide of MPA (MPAG) which is not pharmacologically active. In vivo, MPAG is converted to MPA via enterohepatic recirculation. The following metabolites of the 2-hydroxyethyl-morpholino moiety are also recovered in the urine following oral administration of mycophenolate mofetil to healthy subjects: N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and the N-oxide of N-(2-hydroxyethyl)-morpholine. Cytochrome P450 isozymes, CYP3A4/5 and to a lesser extent by CYP2C8, is responsible for the biotransformation of MPA to 6-O-desmethyl-mycophenolic acid.

SubstrateEnzymesProduct
Mycophenolate mofetil
Not Available
Mycophenolic acid (MPA)Details
Mycophenolate mofetil
Not Available
Mycophenolic acid glucuronideDetails
Mycophenolate mofetil
Not Available
N-(2-carboxymethyl)-morpholineDetails
Mycophenolate mofetil
Not Available
N-(2-hydroxyethyl)-morpholineDetails
Mycophenolate mofetil
Not Available
N-(2-hydroxyethyl)-morpholine N-oxideDetails
Route of eliminationNegligible amount of drug is excreted as MPA (< 1% of dose) in the urine. When orally administered, mycophenolate mofetil was completely recovered with 93% of the dose found in the urine and 6% found in feces. 87% of the administered dose is excreted in the urine as MPAG.
Half lifeThe mean elimination half-life for mycophenolic acid (the active metabolite) ranges from 8-16 hours, while that of the MPAG metabolite ranges from 13-17 hours.
Clearance
  • 193 mL/min [plasma clearance, MPA, oral administration]
  • 177 mL/min [plasma clearance, MPA, IV administration]
  • 15.5 mL/min [renal clearance, MPAG, delayed-release tablet]
ToxicityOral (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
PathwayCategorySMPDB ID
Mycophenolic Acid Metabolism PathwayDrug metabolismSMP00652
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8938
Blood Brain Barrier+0.8594
Caco-2 permeable+0.5904
P-glycoprotein substrateSubstrate0.8908
P-glycoprotein inhibitor IInhibitor0.8381
P-glycoprotein inhibitor IIInhibitor0.8061
Renal organic cation transporterInhibitor0.5379
CYP450 2C9 substrateNon-substrate0.8528
CYP450 2D6 substrateNon-substrate0.602
CYP450 3A4 substrateSubstrate0.7646
CYP450 1A2 substrateNon-inhibitor0.6878
CYP450 2C9 inhibitorNon-inhibitor0.9155
CYP450 2D6 inhibitorNon-inhibitor0.7684
CYP450 2C19 inhibitorNon-inhibitor0.9122
CYP450 3A4 inhibitorNon-inhibitor0.8316
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8664
Ames testNon AMES toxic0.6484
CarcinogenicityNon-carcinogens0.953
BiodegradationNot ready biodegradable0.658
Rat acute toxicity3.0412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.771
hERG inhibition (predictor II)Non-inhibitor0.7653
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Accord healthcare inc usa
  • Apotex corp
  • Endo pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Sandoz inc
  • Strides arcolab ltd
  • Teva pharmaceuticals usa
  • Zydus pharmaceuticals usa inc
  • Accord healthcare inc
  • Apotex inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg/1
Capsuleoral250 mg
Injection, powder, lyophilized, for solutionintravenous500 mg/20mL
Powder for suspensionoral200 mg
Powder, for suspensionoral200 mg/mL
Tabletoral500 mg
Tablet, film coatedoral500 mg/1
Powder for solutionintravenous500 mg
Tabletoral500 mg/1
Tablet, coatedoral500 mg/1
Prices
Unit descriptionCostUnit
CellCept 200 mg/ml Suspension 175ml Bottle875.84USD bottle
Cellcept 500 mg vial65.03USD vial
Cellcept 500 mg tablet10.43USD tablet
Mycophenolate Mofetil 500 mg tablet8.25USD tablet
Mycophenolate 500 mg tablet7.93USD tablet
CellCept 250 mg capsule5.21USD capsule
Mycophenolate Mofetil 250 mg capsule4.13USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1333285 No1994-11-292011-11-29Canada
CA2172506 No2007-07-172014-09-27Canada
US5543408 No1993-09-152013-09-15Us
US5688529 No1994-11-182014-11-18Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySlightly soluble (43 mg/mL at pH 7.4)Not Available
logP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.095 mg/mLALOGPS
logP2.17ALOGPS
logP3.47ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)6.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.53 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.1 m3·mol-1ChemAxon
Polarizability45.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Roger C. Fu, De-Mei Leung, Jeffrey S. Fleitman, Michele C. Rizzolio, Andrew R. Miksztal, “Process for preparing pharmaceutical compositions containing crystalline anhydrous mycophenolate mofetil salts.” U.S. Patent US5545637, issued November, 1988.

US5545637
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 ]
  2. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (200 KB)
MSDSDownload (82.3 KB)
Interactions
Drug Interactions
Drug
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Mycophenolate mofetil resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmdinocillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Amdinocillin resulting in a loss in efficacy.
AmoxicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Amoxicillin resulting in a loss in efficacy.
AmpicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Ampicillin resulting in a loss in efficacy.
AzidocillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Azidocillin resulting in a loss in efficacy.
AzlocillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Azlocillin resulting in a loss in efficacy.
BacampicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Bacampicillin resulting in a loss in efficacy.
BenzylpenicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Benzylpenicillin resulting in a loss in efficacy.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Mycophenolate mofetil resulting in a reduced serum concentration and potentially a decrease in efficacy.
CarbenicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Carbenicillin resulting in a loss in efficacy.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Mycophenolate mofetil.
CholestyramineThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Cholestyramine.
CloxacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Cloxacillin resulting in a loss in efficacy.
ColesevelamThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Colesevelam.
CyclacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Cyclacillin resulting in a loss in efficacy.
CyclosporineThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Cyclosporine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Mycophenolate mofetil.
DicloxacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Dicloxacillin resulting in a loss in efficacy.
EsomeprazoleThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Esomeprazole.
FlucloxacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Flucloxacillin resulting in a loss in efficacy.
GanciclovirThe serum concentration of Ganciclovir can be increased when it is combined with Mycophenolate mofetil.
HetacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Hetacillin resulting in a loss in efficacy.
IsavuconazoniumThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Isavuconazonium.
LansoprazoleThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Lansoprazole.
LeflunomideThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Leflunomide.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Mycophenolate mofetil resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium SulfateThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Magnesium Sulfate.
MeticillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Meticillin resulting in a loss in efficacy.
MetronidazoleThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Metronidazole.
MezlocillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Mezlocillin resulting in a loss in efficacy.
NafcillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Nafcillin resulting in a loss in efficacy.
NatalizumabThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Natalizumab.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Mycophenolate mofetil.
OmeprazoleThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Omeprazole.
OxacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Oxacillin resulting in a loss in efficacy.
PantoprazoleThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Pantoprazole.
PhenoxymethylpenicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Phenoxymethylpenicillin resulting in a loss in efficacy.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Mycophenolate mofetil.
PiperacillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Piperacillin resulting in a loss in efficacy.
PivampicillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Pivampicillin resulting in a loss in efficacy.
PivmecillinamThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Pivmecillinam resulting in a loss in efficacy.
ProbenecidThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Probenecid.
RifabutinThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Rifabutin.
RoflumilastRoflumilast may increase the immunosuppressive activities of Mycophenolate mofetil.
SevelamerThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Sevelamer.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Mycophenolate mofetil.
SparfloxacinThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Sparfloxacin.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Mycophenolate mofetil.
TeriflunomideThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Teriflunomide.
TicarcillinThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Ticarcillin resulting in a loss in efficacy.
TofacitinibMycophenolate mofetil may increase the immunosuppressive activities of Tofacitinib.
TrastuzumabTrastuzumab may increase the neutropenic activities of Mycophenolate mofetil.
ValaciclovirThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Valaciclovir.
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

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 plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH1
Uniprot ID:
P20839
Molecular Weight:
55405.365 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174 ]
  4. Wang J, Yang JW, Zeevi A, Webber SA, Girnita DM, Selby R, Fu J, Shah T, Pravica V, Hutchinson IV, Burckart GJ: IMPDH1 gene polymorphisms and association with acute rejection in renal transplant patients. Clin Pharmacol Ther. 2008 May;83(5):711-7. Epub 2007 Sep 12. [PubMed:17851563 ]
  5. Sanquer S, Maison P, Tomkiewicz C, Macquin-Mavier I, Legendre C, Barouki R, Lang P: Expression of inosine monophosphate dehydrogenase type I and type II after mycophenolate mofetil treatment: a 2-year follow-up in kidney transplantation. Clin Pharmacol Ther. 2008 Feb;83(2):328-35. Epub 2007 Aug 22. [PubMed:17713475 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in t...
Gene Name:
IMPDH2
Uniprot ID:
P12268
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. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174 ]
  3. 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 IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 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:
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 regulator of isoform 1.
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
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 transferase activity but acts as a negative regulator of isoform 1 (By similarity).
Gene Name:
UGT1A6
Uniprot ID:
P19224
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 ]
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 transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular Weight:
59940.495 Da
References
  1. 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 suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. 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:
Steroid 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 regulator of isoform 1.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular Weight:
59741.035 Da
References
  1. Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein kinase c 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 regulator of isoform 1.
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular Weight:
59809.075 Da
References
  1. Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, Satoh S: Involvement of carboxylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos. 2010 Dec;38(12):2210-7. doi: 10.1124/dmd.110.034249. Epub 2010 Sep 7. [PubMed:20823294 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Methylumbelliferyl-acetate deacetylase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular Weight:
61806.41 Da
References
  1. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, Satoh S: Involvement of carboxylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos. 2010 Dec;38(12):2210-7. doi: 10.1124/dmd.110.034249. Epub 2010 Sep 7. [PubMed:20823294 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Miura M, Satoh S, Inoue K, Kagaya H, Saito M, Inoue T, Suzuki T, Habuchi T: Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9. Epub 2007 Sep 29. [PubMed:17906856 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular Weight:
77402.175 Da
References
  1. Michelon H, Konig J, Durrbach A, Quteineh L, Verstuyft C, Furlan V, Ferlicot S, Letierce A, Charpentier B, Fromm MF, Becquemont L: SLCO1B1 genetic polymorphism influences mycophenolic acid tolerance in renal transplant recipients. Pharmacogenomics. 2010 Dec;11(12):1703-13. doi: 10.2217/pgs.10.132. [PubMed:21142914 ]
  2. Miura M, Satoh S, Inoue K, Kagaya H, Saito M, Inoue T, Suzuki T, Habuchi T: Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9. Epub 2007 Sep 29. [PubMed:17906856 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Miura M, Satoh S, Inoue K, Kagaya H, Saito M, Inoue T, Suzuki T, Habuchi T: Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9. Epub 2007 Sep 29. [PubMed:17906856 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. Miura M, Kagaya H, Satoh S, Inoue K, Saito M, Habuchi T, Suzuki T: Influence of drug transporters and UGT polymorphisms on pharmacokinetics of phenolic glucuronide metabolite of mycophenolic acid in Japanese renal transplant recipients. Ther Drug Monit. 2008 Oct;30(5):559-64. doi: 10.1097/FTD.0b013e3181838063. [PubMed:18695635 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Miura M, Kagaya H, Satoh S, Inoue K, Saito M, Habuchi T, Suzuki T: Influence of drug transporters and UGT polymorphisms on pharmacokinetics of phenolic glucuronide metabolite of mycophenolic acid in Japanese renal transplant recipients. Ther Drug Monit. 2008 Oct;30(5):559-64. doi: 10.1097/FTD.0b013e3181838063. [PubMed:18695635 ]
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Drug created on June 13, 2005 07:24 / Updated on May 17, 2016 11:47