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    Chemistry

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    Also known as: 128794-94-5, Cellcept, 115007-34-6, Rs 61443, Myfenax, Rs-61443
    Molecular Formula
    C23H31NO7
    Molecular Weight
    433.5  g/mol
    InChI Key
    RTGDFNSFWBGLEC-SYZQJQIISA-N
    FDA UNII
    9242ECW6R0
    Mycophenolate Mofetil
    Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.
    1 2D Structure

    Mycophenolate Mofetil

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
    2.1.2 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+
    2.1.3 InChI Key
    RTGDFNSFWBGLEC-SYZQJQIISA-N
    2.1.4 Canonical SMILES
    CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OCCN3CCOCC3)O
    2.1.5 Isomeric SMILES
    CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)OCCN3CCOCC3)O
    2.2 Other Identifiers
    2.2.1 UNII
    9242ECW6R0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cellcept

    2. Mofetil Hydrochloride, Mycophenolate

    3. Mofetil, Mycophenolate

    4. Mycophenolate Mofetil Hydrochloride

    5. Mycophenolate Sodium

    6. Mycophenolate, Sodium

    7. Mycophenolic Acid

    8. Mycophenolic Acid Morpholinoethyl Ester

    9. Myfortic

    10. Rs 61443

    11. Rs-61443

    12. Rs61443

    13. Sodium Mycophenolate

    2.3.2 Depositor-Supplied Synonyms

    1. 128794-94-5

    2. Cellcept

    3. 115007-34-6

    4. Rs 61443

    5. Myfenax

    6. Rs-61443

    7. Tm-mmf

    8. Myclausen

    9. Mycophenylate Mofetil

    10. Mycophenolic Acid Morpholinoethyl Ester

    11. Mycophenolatemofetil

    12. Mycophenolate Mofetil Teva

    13. Chebi:8764

    14. 2-morpholin-4-ylethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-2-benzofuran-5-yl)-4-methylhex-4-enoate

    15. Cellcept (tn)

    16. (e)-2-morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate

    17. Nsc-724229

    18. Nsc-758905

    19. 2-morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate

    20. Mycophenolate Mofetil (cellcept)

    21. 9242ecw6r0

    22. 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

    23. 2-morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate

    24. 4-hexenoic Acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl Ester, (e)-

    25. Munoloc

    26. Dsstox_cid_3340

    27. Dsstox_rid_76982

    28. Dsstox_gsid_23340

    29. Mycophenolate Mofetil 100 Microg/ml In Acetonitrile

    30. Mycophenolic Acid 2-(4-morpholinyl)ethyl Ester

    31. Nsc 758905

    32. 2-morpholin-4-ylethyl (4e)-6-[4-hydroxy-7-methyl-6-(methyloxy)-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate

    33. 2-morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate

    34. 4-hexenoic Acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl Ester, (4e)-

    35. Smr002544686

    36. Mmf Cellcept(tm)

    37. Cas-128794-94-5

    38. Hsdb 7436

    39. Me-mpa

    40. Sr-05000001485

    41. Mycophenolate Mofetil [usan]

    42. Arzip

    43. Unii-9242ecw6r0

    44. Mycophenolatmofetil

    45. Mycophenolate Mofetil [usan:usp]

    46. Ncgc00159459-02

    47. (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-isobenzofuran-5-yl)-4-methyl-4-hexenoic Acid 2-(4-morpholinyl)ethyl Ester

    48. Mycophenolate-mofetil

    49. Mofetil Mycophenolate

    50. Mfcd00867568

    51. R-99

    52. Schembl4195

    53. Chembl1456

    54. Mls003915627

    55. Mls004774133

    56. Mls006011929

    57. Schembl218782

    58. Gtpl6831

    59. Dtxsid3023340

    60. Chebi:93612

    61. Mycophenolate Mofetil (jan/usp)

    62. Hms2090a03

    63. Pharmakon1600-01504567

    64. Mycophenolate Mofetil [jan]

    65. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-isobenzofuran-5-yl)-4-methyl-4-hexenoic Acid 2-(4-morpholinyl)ethyl Ester

    66. Act01993

    67. Albb-027273

    68. Hy-b0199

    69. Mycophenolate Mofetil [hsdb]

    70. Tox21_111686

    71. Bbl029073

    72. Bdbm50248299

    73. Mycophenolate Mofetil [vandf]

    74. Nsc724229

    75. Nsc758905

    76. S1501

    77. Stl146382

    78. Zinc21297660

    79. Mycophenolate Mofetil [mart.]

    80. Akos005720900

    81. Mycophenolate Mofetil [usp-rs]

    82. Mycophenolate Mofetil [who-dd]

    83. Tox21_111686_1

    84. Ac-1562

    85. Bcp9000969

    86. Ccg-213315

    87. Db00688

    88. Ks-1209

    89. Nsc 724229

    90. Rs61443

    91. Mycophenolate Mofetil [ema Epar]

    92. Mycophenolate Mofetil, >=98% (hplc)

    93. Ncgc00159459-03

    94. Ncgc00159459-04

    95. 2-morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-isobenzofuran-5-yl)-4-methyl-hex-4-enoate

    96. Bm164622

    97. Ls-15013

    98. Smr004703518

    99. Mycophenolate Mofetil [orange Book]

    100. Mycophenolate Mofetil [ep Monograph]

    101. M2387

    102. Mycophenolate Mofetil [usp Monograph]

    103. Mycophenolate Mofetil For Peak Identification

    104. Sw219893-1

    105. C07908

    106. D00752

    107. W18801

    108. Ab01274794-01

    109. Ab01274794-02

    110. Ab01274794_03

    111. Ab01274794_04

    112. 007m346

    113. A803280

    114. A805863

    115. A888971

    116. J-005626

    117. Q-101316

    118. Q4567614

    119. Sr-05000001485-1

    120. Sr-05000001485-2

    121. Brd-k92428153-001-01-0

    122. Mycophenolic Acid 2-(4-morpholinyl)ethyl Ester [mi]

    123. Mycophenolate Mofetil, European Pharmacopoeia (ep) Reference Standard

    124. Mycophenolate Mofetil, United States Pharmacopeia (usp) Reference Standard

    125. Mycophenolate Mofetil For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    126. Mycophenolate Mofetil, Pharmaceutical Secondary Standard; Certified Reference Material

    127. (1s,3r,4s)-2-amino-9-[4-(benzyloxy)-3-(benzyloxymethyl)-2-methylidene-cyclopentyl]-3h-purin-6-one

    128. (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-morpholinyl)ethyl Ester

    129. 140401-05-4

    130. 2-(4-morpholino)ethyl (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl)-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

    131. 2-(4-morpholinyl)ethyl (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

    132. 2-morpholin-4-ylethyl (e)-6-(6-methoxy-7-methyl-4-oxidanyl-3-oxidanylidene-1h-2-benzofuran-5-yl)-4-methyl-hex-4-enoate

    133. 4-hexenoic Acid,3-dihydro-4-hydroxy-6-methoxy-7-methyl -3-oxo-5-isobenzofuranyl)-4-methyl-, 2-(4-morpholinyl)ethyl Ester, (4e)

    134. 6-((7-hydroxy-5-methoxy-4-methyl-1-oxo-3h-isobenzofuran-6-yl))-4-methyl-hex-4-enoic Acid 2-morpholinoethyl Ester

    135. 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-morpholinyl)ethyl Ester

    136. Morpholinoethyl (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

    137. Morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)- 4-methylhex-4-enoate

    138. Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

    139. Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 433.5 g/mol
    Molecular Formula C23H31NO7
    XLogP33.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count10
    Exact Mass433.21005233 g/mol
    Monoisotopic Mass433.21005233 g/mol
    Topological Polar Surface Area94.5 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity646
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCellcept
    PubMed HealthMycophenolate
    Drug ClassesImmune Suppressant
    Drug LabelCellCept (mycophenolate mofetil) is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent; inosine monophosphate dehydrogenase (IMPDH) inhibitor.The chemical name for mycophenolate mofetil (MMF) is 2-morpholinoethyl (E)-6...
    Active IngredientMycophenolate mofetil; Mycophenolate mofetil hydrochloride
    Dosage FormInjectable; Tablet; Capsule; Suspension
    RouteInjection; Oral
    Strength500mg/vial; 250mg; 200mg/ml; 500mg
    Market StatusPrescription
    CompanyRoche Palo

    2 of 4  
    Drug NameMycophenolate mofetil
    PubMed HealthMycophenolate Mofetil (Oral route)
    Drug ClassesImmune Suppressant
    Drug LabelMycophenolate mofetil is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent; inosine monophosphate dehydrogenase (IMPDH) inhibitor. The chemical name for mycophenolate mofetil (MMF) is 2-morpholinoethyl (E)-6-(1, 3-dih...
    Active IngredientMycophenolate mofetil
    Dosage FormTablet; Capsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanyVintage Pharms; Apotex; Accord Hlthcare; Alkem Labs; Sandoz; Roxane; Strides Pharma; Teva Pharms; Dr Reddys Labs; Mylan

    3 of 4  
    Drug NameCellcept
    PubMed HealthMycophenolate
    Drug ClassesImmune Suppressant
    Drug LabelCellCept (mycophenolate mofetil) is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent; inosine monophosphate dehydrogenase (IMPDH) inhibitor.The chemical name for mycophenolate mofetil (MMF) is 2-morpholinoethyl (E)-6...
    Active IngredientMycophenolate mofetil; Mycophenolate mofetil hydrochloride
    Dosage FormInjectable; Tablet; Capsule; Suspension
    RouteInjection; Oral
    Strength500mg/vial; 250mg; 200mg/ml; 500mg
    Market StatusPrescription
    CompanyRoche Palo

    4 of 4  
    Drug NameMycophenolate mofetil
    PubMed HealthMycophenolate Mofetil (Oral route)
    Drug ClassesImmune Suppressant
    Drug LabelMycophenolate mofetil is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent; inosine monophosphate dehydrogenase (IMPDH) inhibitor. The chemical name for mycophenolate mofetil (MMF) is 2-morpholinoethyl (E)-6-(1, 3-dih...
    Active IngredientMycophenolate mofetil
    Dosage FormTablet; Capsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanyVintage Pharms; Apotex; Accord Hlthcare; Alkem Labs; Sandoz; Roxane; Strides Pharma; Teva Pharms; Dr Reddys Labs; Mylan

    4.2 Therapeutic Uses

    Anti-Inflammatory Agents, Non-Steroidal, Antineoplastic Agents, Dermatologic Agents, Enzyme Inhibitors, Immunosuppressive Agents

    National Library of Medicine, SIS; ChemIDplus Record for Mycophenolate Mofetil (128794-94-5), MESH Heading. Available from, as of March 15, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp

    MEDICATION: Immunosuppressant

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1132

    Mycophenolate is indicated, in combination with cyclosporine and corticosteroids, for prevention of rejection of allogeneic cardiac, hepatic and renal transplants. /Included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2141

    Mycophenolate is indicated for the treatment of lupus nephritis. /NOT included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2141

    4.3 Drug Warning

    Severe GI bleeding (requiring hospitalization) has occurred in 3, 1.7, or 5.4% of renal, cardiac, or hepatic transplant recipients, respectively, receiving 3-g daily dosages of mycophenolate mofetil in clinical studies. Because mycophenolate mofetil has been associated rarely with an increased incidence of adverse GI effects (e.g., ulceration, hemorrhage, perforation), the drug should be administered with caution in patients with active serious GI disease.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3676

    FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2142

    Severe neutropenia (i.e., absolute neutrophil counts (ANC) of less than 500/cu mm) has been reported in up to 2, 2.8, or 3.6% of renal, cardiac, or hepatic allograft recipients, respectively, receiving 3-g daily dosages of mycophenolate mofetil. Neutropenia has been observed most frequently between 31-180 days post-transplant in patients receiving immunosuppressive therapy for the prevention of rejection of kidney, heart, or liver allograft. Neutropenia may be related to mycophenolate mofetil, concomitant therapies, viral infection, or a combination of these causes.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3676

    Potential for the development of lymphoma and other malignancies, particularly of the skin, which may result from immunosuppression. Because of the increased risk for skin cancer, patients should be advised to limit their exposure to sunlight or other UV light by wearing protective clothing and using sunscreen with a high protection factor. Lymphoproliferative disease or lymphoma occurred in 0.4-1% of allograft recipients receiving mycophenolate mofetil in conjunction with other immunosuppressive agents in clinical studies. Non-melanoma skin carcinoma was reported in 1.6-4.2% of patients while other types of malignancy were reported in 0.7-2.1% of patients.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3675

    For more Drug Warnings (Complete) data for MYCOPHENOLATE MOFETIL (15 total), please visit the HSDB record page.

    4.4 Drug Indication

    Mycophenolate mofetil is indicated for the prophylaxis of organ rejection in patients undergoing allogeneic renal, hepatic, or cardiac transplants. It should be used with cyclosporine and corticosteroids. Mycophenolate mofetil may also be used off-label as a second-line treatment for autoimmune hepatitis that has not responded adequately to first-line therapy. Other off-label uses of this drug include lupus-associated nephritis and dermatitis in children.

    FDA Label

    Myfenax is indicated in combination with ciclosporin and corticosteroids for the prophylaxis of acute transplant rejection in patients receiving allogeneic renal, cardiac or hepatic transplants.

    Mycophenolate mofetil Teva is indicated in combination with ciclosporin and corticosteroids for the prophylaxis of acute transplant rejection in patients receiving allogeneic renal, cardiac or hepatic transplants.

    CellCept is indicated in combination with ciclosporin and corticosteroids for the prophylaxis of acute transplant rejection in patients receiving allogeneic renal, cardiac or hepatic transplants.

    Myclausen is indicated in combination with ciclosporin and corticosteroids for the prophylaxis of acute transplant rejection in patients receiving allogeneic renal, cardiac or hepatic transplants.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Mycophenolate mofetil is a prodrug of mycophenolic acid (MPA). The active form of mycophenolate, MPA, prevents the proliferation of immune cells and the formation of antibodies that cause transplant rejection. The above effects lead to higher rates of successful transplantation, avoiding the devastating effects of graft rejection.

    5.2 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antibiotics, Antineoplastic

    Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

    Antibiotics, Antitubercular

    Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic. (See all compounds classified as Antibiotics, Antitubercular.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Antimetabolite Immunosuppressant [EPC]
    5.4 ATC Code

    L04AA06

    L04AA06

    L04AA06

    L04AA06

    5.5 Absorption, Distribution and Excretion

    Absorption

    Mycophenolate mofetil is rapidly absorbed in the small intestine. The maximum concentration of its active metabolite, MPA, is attained 60 to 90 minutes following an oral dose. The average bioavailability of orally administered mycophenolate mofetil in a pharmacokinetic study of 12 healthy patients was 94%. In healthy volunteers, the Cmax of mycophenolate mofetil was 24.5 (9.5)g/mL. In renal transplant patients 5 days post-transplant, Cmax was 12.0 (3.82) g/mL, increasing to 24.1 (12.1)g/mL 3 months after transplantation. AUC values were 63.9 (16.2) gh/mL in healthy volunteers after one dose, and 40.8 (11.4) gh/mL, and 65.3 (35.4)gh/mL 5 days and 3 months after a renal transplant, respectively. The absorption of mycophenolate mofetil is not affected by food.

    Route of Elimination

    A small amount of drug is excreted as MPA in the urine (less than 1%). When mycophenolate mofetil was given orally in a pharmacokinetic study, it was found to be 93% excreted in urine and 6% excreted in feces. Approximately 87% of the entire administered dose is found to be excreted in the urine as MPAG, an inactive metabolite.

    Volume of Distribution

    The volume of distribution of mycophenolate mofetil is 3.6 (1.5) to 4.0 (1.2) L/kg.

    Clearance

    Plasma clearance of mycophenolate mofetil is 193 mL/min after an oral dose and 177 (31) mL/min after an intravenous dose.

    /Absorption/ is rapid and extensive after oral administration.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2142

    In 12 healthy volunteers, the mean absolute bioavailability of oral mycophenolate mofetil relative to intravenous mycophenolate mofetil (based on MPA AUC) was 94%. The area under the plasma-concentration time curve (AUC) for MPA appears to increase in a dose-proportional fashion in renal transplant patients receiving multiple doses of mycophenolate mofetil up to a daily dose of 3 g.

    Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2752

    Protein binding: To plasma albumin: High (97% for mycophenolic acid (MPA) at concentration ranges normally seen in stable renal transplant patients). At higher mycophenolic acid glucuronide (MPAG) concentrations (e.g., in patients with renal impairment or delayed graft function), binding of MPA may be decreased as a result of competition between MPA and MPAG for binding sites.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2142

    The mean (+/-SD) apparent volume of distribution of MPA in 12 healthy volunteers is approximately 3.6 (+/-1.5) and 4.0 (+/-1.2) L/kg following intravenous and oral administration, respectively. MPA, at clinically relevant concentrations, is 97% bound to plasma albumin. MPAG is 82% bound to plasma albumin at MPAG concentration ranges that are normally seen in stable renal transplant patients; however, at higher MPAG concentrations (observed in patients with renal impairment or delayed renal graft function), the binding of MPA may be reduced as a result of competition between MPAG and MPA for protein binding. Mean blood to plasma ratio of radioactivity concentrations was approximately 0.6 indicating that MPA and MPAG do not extensively distribute into the cellular fractions of blood.

    Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2752

    For more Absorption, Distribution and Excretion (Complete) data for MYCOPHENOLATE MOFETIL (9 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    After both oral and intravenous administration mycophenolate mofetil is entirely metabolized by liver carboxylesterases 1 and 2 to mycophenolic acid (MPA), the active parent drug. It is then metabolized by the enzyme glucuronyl transferase, producing the inactive phenolic glucuronide of MPA (MPAG). The glucuronide metabolite is important, as it is then converted to MPA through enterohepatic recirculation. Mycophenolate mofetil that escapes metabolism in the intestine enters the liver via the portal vein and is transformed to pharmacologically active MPA in the liver cells.N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and the N-oxide portion of N-(2-hydroxyethyl)-morpholine are additional metabolites of MMF occurring in the intestine as a result of liver carboxylesterase 2 activity. UGT1A9 and UGT2B7 in the liver are the major enzymes contributing to the metabolism of MPA in addition to other UGT enzymes, which also play a role in MPA metabolism. The four major metabolites of MPA are 7-O-MPA--glucuronide (MPAG, inactive), MPA acyl-glucuronide (AcMPAG), produced by uridine 5-diphosphate glucuronosyltransferases (UGT) activities, 7-O-MPA glucoside produced via UGT, and small amounts 6-O-des-methyl-MPA (DM-MPA) via CYP3A4/5 and CYP2C8 enzymes.

    Following oral and intravenous dosing, mycophenolate mofetil undergoes complete metabolism to MPA /mycophenolic acid/, 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.

    Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2752

    5.7 Biological Half-Life

    The average apparent half-life of mycophenolate mofetil is 17.9 (6.5) hours after oral administration and 16.6 (5.8) hours after intravenous administration.

    For mycophenolic acid (MPA):Mean apparent: Approximately 17.9 hours after oral administration and 16.6 hours after intravenous administration.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2142

    Mean (+/-SD) apparent half-life and plasma clearance of MPA are 17.9 (+/-6.5) hours and 193 (+/-48) mL/min following oral administration and 16.6 (+/-5.8) hours and 177 (+/-31) mL/min following intravenous administration, respectively.

    Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2752

    5.8 Mechanism of Action

    The active metabolite of mycophenolate, mycophenolic acid, prevents T-cell and B-cell proliferation and the production of cytotoxic T-cells and antibodies. Lymphocyte and monocyte adhesion to endothelial cells of blood vessels that normally part of inflammation is prevented via the glycosylation of cell adhesion molecules by MPA. MPA inhibits de novo purine biosynthesis (that promotes immune cell proliferation) by inhibiting inosine 5-monophosphate dehydrogenase enzyme (IMPDH), with a preferential inhibition of IMPDH II. IMPDH normally transforms inosine monophosphate (IMP) to xanthine monophosphate (XMP), a metabolite contributing to the production of guanosine triphosphate (GTP). GTP is an important molecule for the synthesis of ribonucleic acid (RNA), deoxyribonucleic acid (DNA), and protein. As a result of the above cascade of effects, mycophenolate mofetil reduces de-novo production of guanosine nucleotides, interfering with the synthesis of DNA, RNA, and protein required for immune cell production. Further contributing to the above anti-inflammatory effects, MMF depletes tetrahydrobiopterin, causing the decreased function of inducible nitric oxide synthase enzyme, in turn decreasing the production of peroxynitrite, a molecule that promotes inflammation.

    As a potent, selective, noncompetitive, and reversible, inhibitor of inosine monophosphate dehydrogenase (IMPDH), mycophenolic acid (MPA), the active metabolite /of mycophenolate mofetil/, inhibits the de novo synthesis pathway of guanosine nucleotides without being incorporated into DNA. Because T and B lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, while other cell types can utilize salvage pathways, MPA has potent cytostatic effects on lymphocytes. MPA inhibit proliferative responses of T and B lymphocytes to both mitogenic and allospecific stimulation. The 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 lymphocytes and monocyte glycoproteins that are involved in intercellular adhesion of these cells to endothelial cells, and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection. Mycophenolate mofetil dose not inhibit the early events in the activation of human peripheral blood mononuclear cells, such as the production of interleukin-1 and interleukin-2, but does block the coupling of these events to DNA synthesis and proliferation.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2141

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    02-Jan-2021
    21-Aug-2024
    KGS
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    DOSAGE - CAPSULE;ORAL - 250MG

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