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Identification
NameMycophenolic acid
Accession NumberDB01024  (APRD01603, EXPT02208)
TypeSmall Molecule
GroupsApproved
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
Mycophenolsäure
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Myfortictablet (enteric-coated)180 mgoralNovartis Pharmaceuticals Canada Inc2005-02-11Not applicableCanada
Myfortictablet, delayed release180 mg/1oralAvera Mc Kennan Hospital2015-03-01Not applicableUs
Myfortictablet, delayed release360 mg/1oralNovartis Pharmaceuticals Corporation2004-02-27Not applicableUs
Myfortictablet, delayed release180 mg/1oralNovartis Pharmaceuticals Corporation2004-02-27Not applicableUs
Myfortictablet (enteric-coated)360 mgoralNovartis Pharmaceuticals Canada Inc2005-02-11Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-mycophenolic Acidtablet (enteric-coated)360 mgoralApotex Inc2014-07-02Not applicableCanada
Apo-mycophenolic Acidtablet (enteric-coated)180 mgoralApotex Inc2014-07-02Not applicableCanada
Mycophenolic Acidtablet, delayed release180 mg/1oralMylan Pharmaceuticals Inc.2014-01-08Not applicableUs
Mycophenolic Acidtablet, delayed release180 mg/1oralGolden State Medical Supply, Inc.2014-10-13Not applicableUs
Mycophenolic Acidtablet, delayed release360 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Mycophenolic Acidtablet, delayed release180 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Mycophenolic Acidtablet, delayed release360 mg/1oralMylan Institutional Inc.2014-02-11Not applicableUs
Mycophenolic Acidtablet, delayed release360 mg/1oralApotex Corp2014-08-19Not applicableUs
Mycophenolic Acidtablet, delayed release180 mg/1oralMylan Institutional Inc.2014-02-11Not applicableUs
Mycophenolic Acidtablet, delayed release180 mg/1oralApotex Corp2012-08-21Not applicableUs
Mycophenolic Acidtablet, delayed release360 mg/1oralMylan Pharmaceuticals Inc.2014-01-08Not applicableUs
Mycophenolic Acidtablet, delayed release360 mg/1oralGolden State Medical Supply, Inc.2014-10-13Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MelbexNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mycophenolate sodium
ThumbNot applicableDBSALT001740
Categories
UNIIHU9DX48N0T
CAS number24280-93-1
WeightAverage: 320.3371
Monoisotopic: 320.125988372
Chemical FormulaC17H20O6
InChI KeyInChIKey=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
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
  • Medium-chain fatty acid
  • Anisole
  • Methyl-branched fatty acid
  • Heterocyclic fatty acid
  • Branched fatty acid
  • Alkyl aryl ether
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Vinylogous acid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the prophylaxis of organ rejection in patients receiving allogeneic renal transplants, administered in combination with cyclosporine and corticosteroids.
PharmacodynamicsMycophenolic 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 actionMycophenolic 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.
Related Articles
AbsorptionBioavailability 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.

SubstrateEnzymesProduct
Mycophenolic acid
Mycophenolic acid-acyl glucuronideDetails
Mycophenolic acid
6-O-desmethyl-mycophenolic acidDetails
Mycophenolic acid
Mycophenolic acid-7-O-glucuornideDetails
Route of eliminationNot Available
Half lifeThe 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]
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+0.9409
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, delayed releaseoral180 mg/1
Tablet, delayed releaseoral360 mg/1
Tablet (enteric-coated)oral180 mg
Tablet (enteric-coated)oral360 mg
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)
CA2250906 No2006-10-032017-04-10Canada
US6025391 No1997-04-102017-04-10Us
US6172107 No1997-04-102017-04-10Us
US6306900 No1998-02-272018-02-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point141 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
ATC CodesL04AA06
AHFS Codes
  • 92:00.00
PDB Entries
FDA labelNot Available
MSDSDownload (74 KB)
Interactions
Drug Interactions
Drug
AciclovirThe serum concentration of Mycophenolic acid can be increased when it is combined with Aciclovir.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Mycophenolic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmdinocillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Amdinocillin resulting in a loss in efficacy.
AmoxicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Amoxicillin resulting in a loss in efficacy.
AmpicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Ampicillin resulting in a loss in efficacy.
AzidocillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Azidocillin resulting in a loss in efficacy.
AzlocillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Azlocillin resulting in a loss in efficacy.
BacampicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Bacampicillin resulting in a loss in efficacy.
Benzathine benzylpenicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Benzathine benzylpenicillin resulting in a loss in efficacy.
BenzylpenicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Benzylpenicillin resulting in a loss in efficacy.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Mycophenolic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
CarbenicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid 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 Mycophenolic acid.
CholestyramineThe serum concentration of Mycophenolic acid can be decreased when it is combined with Cholestyramine.
CiprofloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Ciprofloxacin.
CloxacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Cloxacillin resulting in a loss in efficacy.
ColesevelamThe serum concentration of Mycophenolic acid can be decreased when it is combined with Colesevelam.
ColestipolThe serum concentration of Mycophenolic acid can be decreased when it is combined with Colestipol.
CyclacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Cyclacillin resulting in a loss in efficacy.
CyclosporineThe serum concentration of Mycophenolic acid can be decreased when it is combined with Cyclosporine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Mycophenolic acid.
DicloxacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Dicloxacillin resulting in a loss in efficacy.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Mycophenolic acid.
EsomeprazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Esomeprazole.
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Mycophenolic acid.
FlucloxacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid 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 Mycophenolic acid.
GemifloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Gemifloxacin.
HetacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Hetacillin resulting in a loss in efficacy.
IsavuconazoniumThe serum concentration of Mycophenolic acid can be increased when it is combined with Isavuconazonium.
LansoprazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Lansoprazole.
LeflunomideThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Leflunomide.
LevofloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Levofloxacin.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Mycophenolic acid.
Magnesium chlorideThe serum concentration of Mycophenolic acid can be decreased when it is combined with Magnesium chloride.
Magnesium citrateThe serum concentration of Mycophenolic acid can be decreased when it is combined with Magnesium citrate.
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Mycophenolic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium oxideThe serum concentration of Mycophenolic acid can be decreased when it is combined with Magnesium oxide.
Magnesium salicylateThe serum concentration of Mycophenolic acid can be decreased when it is combined with Magnesium salicylate.
Magnesium SulfateThe serum concentration of Mycophenolic acid can be decreased when it is combined with Magnesium Sulfate.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Mycophenolic acid.
MeticillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Meticillin resulting in a loss in efficacy.
MetronidazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Metronidazole.
MezlocillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Mezlocillin resulting in a loss in efficacy.
MoxifloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Moxifloxacin.
NafcillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Nafcillin resulting in a loss in efficacy.
NatalizumabThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Natalizumab.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Mycophenolic acid.
NorfloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Norfloxacin.
OfloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Ofloxacin.
OmeprazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Omeprazole.
OxacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Oxacillin resulting in a loss in efficacy.
PantoprazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Pantoprazole.
PhenoxymethylpenicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid 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 Mycophenolic acid.
PiperacillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Piperacillin resulting in a loss in efficacy.
PivampicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Pivampicillin resulting in a loss in efficacy.
PivmecillinamThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Pivmecillinam resulting in a loss in efficacy.
ProbenecidThe serum concentration of Mycophenolic acid can be increased when it is combined with Probenecid.
Procaine benzylpenicillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Procaine benzylpenicillin resulting in a loss in efficacy.
RabeprazoleThe serum concentration of Mycophenolic acid can be decreased when it is combined with Rabeprazole.
RifabutinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Mycophenolic acid can be decreased when it is combined with Rifapentine.
RoflumilastRoflumilast may increase the immunosuppressive activities of Mycophenolic acid.
SevelamerThe serum concentration of Mycophenolic acid can be decreased when it is combined with Sevelamer.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Mycophenolic acid.
SparfloxacinThe serum concentration of Mycophenolic acid can be decreased when it is combined with Sparfloxacin.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Mycophenolic acid.
TeriflunomideThe serum concentration of Mycophenolic acid can be increased when it is combined with Teriflunomide.
TicarcillinThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Ticarcillin resulting in a loss in efficacy.
TofacitinibMycophenolic acid may increase the immunosuppressive activities of Tofacitinib.
TrastuzumabTrastuzumab may increase the neutropenic activities of Mycophenolic acid.
ValaciclovirThe serum concentration of Mycophenolic acid can be increased when it is combined with Valaciclovir.
ValganciclovirThe serum concentration of Valganciclovir can be increased when it is combined with Mycophenolic acid.
Food InteractionsNot Available

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:
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. 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 ]
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. 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 ]

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. 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 transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
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 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. 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 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 ]
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Drug created on June 13, 2005 07:24 / Updated on July 28, 2016 01:52