Mycophenolinsäure

Bezeichnung:Mycophenolinsäure

CAS-Nr24280-93-1

Englisch Name:Mycophenolic acid

CBNumberCB8311003

SummenformelC17H20O6

Molgewicht320.34

MOL-Datei24280-93-1.mol

Synonyma

Mycophenolinsure

Mycophenolinsäure

Mycophenolinsäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	141°C
Siedepunkt	419.24°C (rough estimate)
Dichte	1.2300 (rough estimate)
Dampfdruck	0Pa at 22℃
Brechungsindex	1.5200 (estimate)
Flammpunkt	2℃
storage temp.	Sealed in dry,Store in freezer, under -20°C
Löslichkeit	methanol: 50 mg/mL, clear, colorless to faintly yellow
Aggregatzustand	powder
pka	4.5(at 25℃)
Farbe	white to white with yellow cast
Wasserlöslichkeit	13mg/L(25 ºC)
Merck	14,6327
BRN	1295848
BCS Class	2?
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
LogP	-1.83-2.28 at 25℃ and pH5-9
Dissoziationskonstante	4.58-8.05 at 22.5-25℃
CAS Datenbank	24280-93-1(CAS DataBase Reference)
EPA chemische Informationen	4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)- (24280-93-1)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,T,F
R-Sätze:	22-61-40-68-50/53-48/25-52/53-36-20/21/22-11
S-Sätze:	53-45-36/37-61-22-26-16
RIDADR	2811
WGK Germany	3
RTECS-Nr.	MP8050000
F	10
HazardClass	6.1(b)
PackingGroup	III
HS Code	29419090
Toxizität	LD50 in mice (mg/kg): >1250 orally; 972.9±77 i.p. (Williams)

Gefahreninformationscode (GHS)

Mycophenolic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R61:Kann das Kind im Mutterleib schädigen.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Mycophenolic acid is an immunosuppresive microbial metabolite that has been found in P. brevicompactum. It is also an active metabolite of mycophenolate mofetil that is formed via carboxylesterase 1 (CES1) and CES2. Mycophenolic acid is an inhibitor of IMP dehydrogenase (IMPDH) type I and type II (IC₅₀s = 32 and 11 nM, respectively, in cell-free assays) and inhibits DNA synthesis in L strain mouse fibroblasts when used at concentrations ranging from 0.1 to 10 μg/ml. It is active against several strains of C. albicans, C. parakrusei, C. tropicalis, and C. neoformans (MICs = 3.9-31.25 μg/ml), as well as various strains of S. aureus (MICs = 31.25-125 μg/ml). Mycophenolic acid (150 mg/kg) reduces splenomegaly in a mouse model of Friend virus-induced leukemia. It decreases the number of hemolytic plaque forming cells isolated from the spleen of mice immunized with sheep red blood cells (RBCs) when administered at doses ranging from 60 to 240 mg/kg. Formulations containing mycophenolic acid have been used as immunosuppressive agents in the prevention of organ transplant rejection.
Chemische Eigenschaften
White to Off-White Powder
Verwenden
antineoplastic, progestin
Verwenden
immune suppressant, antineoplastic, antiviral
Verwenden
An antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleotides.
Verwenden
Mycophenolic acid is a common Penicillium metabolite first reported in the 1930s as a possible mycotoxin. Re-investigation showed mycophenolic acid to display broad antitumour, antiviral, antifungal and antiprotozoan activities. Its potent immunosuppressant activity led to its commercial development to prevent kidney transplant rejection. Mycophenolic acid acts by inhibiting inosine monophosphate dehydrogenase, controlling the rate of de novo purine synthesis in proliferating B and T lymphocytes.
Definition
ChEBI: A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mo etil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
Trademarks
Myfortic (Novartis).
Allgemeine Beschreibung
Assayed in therapeutic drug monitoring to ensure patients remain within the drug′s therapeutic range, mycophenolic acid is an immunosuppressant drug and the active metabolite of the prodrug mycophenolate mofetil. This analytical standard is suitable for LC-MS/MS applications including therapeutic drug monitoring and other clinical or diagnostic applications.
Biologische Aktivität
Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo . Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation.
Mechanism of action
Mycophenolic acid (MPA) is a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH) that prevents the ab initio biosynthesis of purine nucleotides. It predominantly affects lymphocytes, leading to inhibition of DNA synthesis in T cells and B cells, thereby suppressing cell-mediated immune responses and antibody formation.MPA also inhibits glycosylation and expression of adhesion molecules, as well as the recruitment of lymphocytes and monocytes to sites of inflammation.MPA depletes tetrahydrobiopterin and reduces nitric oxide production via inducible NO synthase without affecting the activity of constitutive NO synthase^[1].
Lager
Room temperature
läuterung methode
Purify the acid by dissolving it in the minimum volume of EtOAc, applying onto a silica gel column (0.05-0.2 mesh) and eluting with a mixture of EtOAc/CHCl3/AcOH (45:55:1) followed by recrystallisation from heptane/EtOAc, from aqueous EtOH or from hot H2O and drying in vacuo. It is a weak dibasic acid, moderately soluble in Et2O, CHCl3 and hot H2O but weakly soluble in *C6H6 and toluene. [Birch & Wright Aust J Chem 22 2635 1969, Canonica et al. J Chem Soc, Perkin Trans 1 2639 1972, Birkinshaw et al. Biochem J 50 630 1952, Beilstein 18 II 393, 18 III/IV 6513.]
Einzelnachweise
[1] ALLISON A. Mechanisms of action of mycophenolate mofetil[J]. Lupus, 2005, 14 1: 2-8. DOI:10.1177/096120330501400102.
Einzelnachweise
References/Citations 1) Eugui et al. (1991), Lymphocyte-selective cyostatic and immunosuppressive effects of mycophenolic acid in vitro: role of deoxyguanosine nucleotide depletion; Scand. J. Immunol., 33 161 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

Mycophenolic acid Upstream-Materialien And Downstream Produkte

Mycophenolinsäure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

24280-93-1, Mycophenolic acid Verwandte Suche:

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