Mycophenolate mofetil

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Structural formula
Structural formula of mycophenolate mofetil
General
Non-proprietary name Mycophenolate mofetil
other names

( E ) -6 - (- 4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl) -4-methylhex-4-enoic acid-2-morpholinoethyl ester ( IUPAC )

Molecular formula C 23 H 31 NO 7
Brief description

white to almost white, crystalline powder

External identifiers / databases
CAS number
EC number 627-027-6
ECHA InfoCard 100.155.374
PubChem 5281078
ChemSpider 4444535
DrugBank DB00688
Wikidata Q4567614
Drug information
ATC code

L04 AA06

Drug class

Immunosuppressant

properties
Molar mass 433.50 g · mol -1
Physical state

firmly

Melting point

93-94 ° C

solubility

practically insoluble in water, slightly soluble in acetone , slightly soluble in absolute ethanol

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-400
P: 273
Toxicological data

500 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mycophenolate mofetil (also mycophenolate mofetil or mycophenolate mofetil, MMF ) is a drug that suppresses the effect of the immune system ( immunosuppressive agent ). It is mainly used in combination with cyclosporine and corticosteroids for the prophylaxis of acute transplant rejection reactions in patients with allogeneic kidney , heart or liver transplants .

history

Mycophenolate mofetil was developed by the pharmaceutical company Syntex . After being taken over by Roche , it was approved in the USA in May 1995 under the name CellCept . In Europe, it was one of the first drugs to be approved in a central approval process for 15 countries.

pharmacology

Mechanism of action

Mycophenolat-Mofetil is the 2-morpholinoethyl ester of mycophenolic acid (MPA) and is converted into this in the body. MPA is a selective, non-competitive and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), which therefore inhibits the synthesis of the guanine- containing nucleotides ( guanosine ). Since the de novo synthesis of purines is essential for the proliferation of T and B lymphocytes , while other cell types can use the recycling metabolism, MPA has a stronger cytostatic effect on lymphocytes than on other cells, whereby these are selectively inhibited.

Side effects

Mycophenolate mofetil has numerous side effects . More common side effects (affecting over 10% of patients) are anemia , thrombocytopenia , nausea, vomiting, and diarrhea . As a result of the suppression of the immune system, more infections ( sepsis , candidiasis , herpes simplex , herpes zoster ) can occur.

Congenital malformations have been reported in children of women who were treated with CellCept in combination with other immunosuppressants during pregnancy. The use of CellCept during pregnancy should be limited to those cases in which no suitable alternative is available. In some cases, progressive multifocal leukoencephalopathy (PML) has been observed as a life-threatening neurological side effect.

In February 2016, Novartis announced in a Rote-Hand-Brief about Myfortic® (mycophenolate sodium; ie the same active metabolite ) and the serious risk of teratogenicity .

Trade names

Monopreparations

CellCept (EU, CH), Myfortic (CH, USA, CDN) and various generics

Web links

Individual evidence

  1. ↑ a b Data sheet MYCOPHENOLATE MOFETIL CRS (PDF) at EDQM , accessed on August 15, 2008.
  2. ↑ a b Entry on mycophenolate mofetil. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.
  3. ↑ a b Data sheet Mycophenolate mofetil, ≥98% (HPLC) from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
  4. ↑ Rote-Hand-Brief on CellCept, November 12, 2007 (PDF; 91 kB).
  5. ↑ Rote-Hand-Brief on CellCept, February 18, 2008 (PDF; 111 kB).
  6. ↑ RHB from Novartis on the website of the Drug Commission of the German Medical Association, accessed on March 1, 2016.