Mycophenolate mofetil

Base Information

• Chemical Name: Mycophenolate mofetil
• CAS No.: 128794-94-5
• Molecular Formula: C23H31NO7
• Molecular Weight: 433.502
• Hs Code.: 29349990
• Mol file: 128794-94-5.mol

Synonyms:Cellcept (TN);RS 61443;2-morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-hex-4-enoate;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)-;Mycophenolate;

Chemical Property of Mycophenolate mofetil

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 7.51E-17mmHg at 25°C
• Melting Point: 95-96 °C
• Refractive Index: 1.557
• Boiling Point: 637.6 °C at 760 mmHg
• PKA: 5.6(at 25℃)
• Flash Point: 339.4 °C
• PSA: 94.53000
• Density: 1.222 g/cm³
• LogP: 2.46190
• Storage Temp.: Store at RT
• Solubility.: DMSO: ≥15mg/mL

Purity/Quality:

99.9% ^*data from raw suppliers

Mycophenolate mofetil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Mycophenolate mofetil was launched in 1995 in the U.S.A., its first market worldwide, for the prevention of acute kidney transplant rejection in conjunction with other immunosuppressive therapy and to treat refractory acute kidney graft rejection. With improved oral absorption and bioavailability, mycophenolate mofetil is a prodrug of mycophenolic acid (MPA), a fermentation product of several Penicillium species. MPA is a selective, reversible, non-competitive inhibitor of inosinate dehydrogenase and guanylate synthetase. It inhibits the de now pathway of purine biosynthesis. MPA was found to have more potent antiproliferative effects on T and B lymphocytes than other cell types. Compared with other immunosuppressants, mycophenolate mofetil is reportedly superior due to its unique mechanism of action and excellent safety profile for long term use. Mycophenolate mofetil is being investigated clinically in the treatment of heart and liver transplantation rejection, asthma, in preventing coronary artery restenosis, and in treating rheumatoid arthritis.
• Uses: An immunosuppressant. For the prophylaxis of organ rejection in patients receiving allogeneic renal, cardiac or hepatic transplants. Mycophenolate mofetil should be used concomitantly with cyclosporine and corticosteroids. Mycophenolate mofetil has been used to treat wild-type embryos for inhibiting nucleotide synthesis.
• Indications: Mycophenolate mofetil (MMF, CellCept) is an ester prodrug of mycophenolic acid (MPA), a Penicillium-derived immunosuppressive agent that blocks de novo purine synthesis by noncompetitively inhibiting the enzyme inosine monophosphate dehydrogenase. MPA preferentially suppresses the proliferation of cells, such as T and B lymphocytes, that lack the purine salvage pathway and must synthesize de novo the guanosine nucleotides required for DNA and RNA synthesis.MPA has been used for decades as a systemic treatment for moderate to severe psoriasis. MMF was developed to increase the bioavailability of MPA.
• Clinical Use: MMF is indicated for the prophylaxis of organ rejection in patients receiving renal, hepatic, and cardiac transplants; it is often used in combination with other immunosuppressive agents for this indication. In dermatology, MMF is particularly useful as monotherapy, or as a steroid-sparing agent, for treatment of autoimmune blistering diseases (bullous pemphigoid and pemphigus). It may also be useful for the treatment of inflammatory skin diseases mediated by neutrophilic infiltration, such as pyoderma gangrenosum, and psoriasis.
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid with clozapine (increased risk of agranulocytosis). Antivirals: higher concentrations of both mycophenolate and aciclovir or ganciclovir when the two are prescribed concomitantly. Antacids: absorption of mycophenolate decreased in presence of magnesium and aluminium salts. Antibacterials: bioavailability of mycophenolate possibly reduced by metronidazole and norfloxacin; concentration of active metabolite reduced by rifampicin. Colestyramine: 40% reduction in oral bioavailability of mycophenolate. Ciclosporin: some studies show that ciclosporin decreases plasma MPA AUC levels; other studies show increases - no dose change required. Iron preparations: may significantly reduce absorption of mycophenolate. Sevelamer: reduced levels of mycophenolate. Tacrolimus: increases MPA concentrations- no dose change required but monitor closely. See 'Other information'

Technology Process of Mycophenolate mofetil

There total 2 articles about Mycophenolate mofetil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-(morpholin-4-yl)ethanol (622-40-2) + mycophenolic acid triethylamine salt → mycophenolate mofetil (128794-94-5)

Guidance literature:

2-(morpholin-4-yl)ethanol; mycophenolic acid triethylamine salt; In o-xylene; at 110 - 120 ℃; for 44 - 47h; pH=6.8 - 7.3;

With sulfuric acid; In o-xylene; water; at 20 - 28 ℃; pH=2.0 - 7.3;

With sodium hydroxide; In water; ethyl acetate; pH=8.0; Product distribution / selectivity;

Reference yield:

2-(morpholin-4-yl)ethanol (622-40-2) + mycophenolic acid triethylamine salt + MPA-OH (26644-03-1) → mycophenolate mofetil (128794-94-5) + C29H42N2O9 (1094322-91-4)

Guidance literature:

In xylene; at 120 - 125 ℃; for 3 - 71h; Conversion of starting material;

upstream raw materials:

2-(morpholin-4-yl)ethanol

MPA-OH

Refernces

• 1、 -. "METHOD FOR THE PURIFICATION OF MYCOPHENOLATE MOFETIL". Page/Page column 7. . Retrieved 2009/03/07.