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128794-94-5

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  • High Quality 99% 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)- 128794-94-5 ISO Producer

    Cas No: 128794-94-5

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  • 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)- 128794-94-5

    Cas No: 128794-94-5

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128794-94-5 Usage

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.

Chemical Properties

White Powder

Originator

Roche (Switzerland)

Uses

Different sources of media describe the Uses of 128794-94-5 differently. You can refer to the following data:
1. An immunosuppressant.
2. 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.
3. Mycophenolate mofetil has been used to treat wild-type embryos for inhibiting nucleotide synthesis.

Definition

ChEBI: A carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases.

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.

Brand name

CellCept

Biochem/physiol Actions

Mycophenolate mofetil is a prodrug of mycophenolic acid (Cat. # M5255) that is cleaved by nonspecific esterases in vivo to produce the parent compound. Mycophenolic acid blocks inosine monophosphate dehydrogenase and is a potent immunosuppresive agent.

Mechanism of action

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.

Side effects

Adverse effects produced by MMF most commonly include nausea, abdominal cramps, diarrhea, and possibly an increased incidence of viral and bacterial infections. Whether MMF may be associated with an increased long-term risk of lymphoma or other malignancies is controversial; however, any such risk is likely to be lower in patients treated for skin disease with MMF monotherapy than in transplant patients treated with combination immunosuppressive therapy.

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'

Metabolism

Mycophenolate undergoes presystemic metabolism in the liver to active mycophenolic acid (MPA). MPA undergoes enterohepatic recirculation and secondary increases in plasma MPA concentrations are seen; these have been reported at between 6-12 hours after a dose of mycophenolate mofetil, and at between 6-8 hours after a dose of mycophenolate sodium. MPA is metabolised by glucuronidation to the inactive mycophenolic acid glucuronide. The majority of a dose of mycophenolate is excreted in the urine as this glucuronide, with negligible amounts of MPA; about 6% of a dose is recovered in faeces.

References

1) Allison and Eugui (1996), Purine metabolism and immunosuppressive effects of mycophenolate mofetil (MMF); Clin. Transplant., 10 77 2) Jonsson et al. (2002), Mycophenolic acid inhibits inosine 5′-monophosphate dehydrogenase and suppresses production of pro-inflammatory cytokines, nitric oxide, and LDH in macrophages; Cell. Immunol., 216 93 3) Allison et al. (1993), Mechanisms of action of mycophenolic acid; Ann. NY Acad. Sci., 696 63 4) Quemeneur et al. (2002), Mycophenolic acid inhibits IL-2-dependent T cell proliferation, but not IL-2-dependent survival and sensitization to apoptosis; J. Immunol., 169 2747 5) Ebrahimi et al. (2012) Time dependent neuroprotection of mycophenolate mofetil; effects on temporal dynamics in glial proliferation, apoptosis, and scar formation; J. Neuroinflammation, 9 89

Check Digit Verification of cas no

The CAS Registry Mumber 128794-94-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,8,7,9 and 4 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 128794-94:
(8*1)+(7*2)+(6*8)+(5*7)+(4*9)+(3*4)+(2*9)+(1*4)=175
175 % 10 = 5
So 128794-94-5 is a valid CAS Registry Number.
InChI:InChI=1/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

128794-94-5 Well-known Company Product Price

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  • TCI America

  • (M2387)  Mycophenolate Mofetil  >98.0%(HPLC)(T)

  • 128794-94-5

  • 100mg

  • 590.00CNY

  • Detail
  • TCI America

  • (M2387)  Mycophenolate Mofetil  >98.0%(HPLC)(T)

  • 128794-94-5

  • 1g

  • 3,500.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000489)  Mycophenolate mofetil  European Pharmacopoeia (EP) Reference Standard

  • 128794-94-5

  • Y0000489

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000519)  Mycophenolate mofetil for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 128794-94-5

  • Y0000519

  • 1,880.19CNY

  • Detail
  • USP

  • (1448956)  Mycophenolate mofetil  United States Pharmacopeia (USP) Reference Standard

  • 128794-94-5

  • 1448956-200MG

  • 4,662.45CNY

  • Detail

128794-94-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name mycophenolate mofetil

1.2 Other means of identification

Product number -
Other names 2-morpholin-4-ylethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:128794-94-5 SDS

128794-94-5Downstream Products

128794-94-5Relevant articles and documents

MYCOPHENOLIC ACID RECYCLING IN A METHOD FOR THE PREPARATION OF MYCOPHENOLATE MOFETIL

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Page/Page column 8-12, (2009/03/07)

The present invention provides a method for the preparation of mycophenolate mofetil wherein mycophenoiic acid is mixed with 2-morpholinoethanol in a water-immiscible solvent, followed by addition of water and adjustment of the pH to a value ranging from 0 to 3 or ranging from 7 to 10 and separating the organic and aqueous phases. Mycophenolate mofetil is isolated from the relevant phase and the mycophenoiic acid present in the alternate phase is re-used in a conversion of mycophenoiic acid to mycophenolate mofetil.

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