89287

Mycophenolic acid

analytical standard

• Synonym(s): 6-(1,3-Dihydro-7-hydroxy-5-methoxy-4-methyl-1-oxoisobenzofuran-6-yl)-4-methyl-4-hexanoic acid, 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid, NSC 129185
• Empirical Formula (Hill Notation): C₁₇H₂₀O₆
• CAS Number: 24280-93-1
• Molecular Weight: 320.34
• Beilstein: 1295848
• EC Number: 246-119-3
• MDL number: MFCD00036814
• PubChem Substance ID: 329769720
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• Assay: ≥98.5% (HPLC)
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• impurities: ≤1.0% water
• application(s): forensics and toxicology; pharmaceutical (small molecule)
• format: neat
• storage temp.: 2-8°C
• SMILES string: COc1c(C)c2COC(=O)c2c(O)c1C\C=C(/C)CCC(O)=O
• InChI: 1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
• InChI key: HPNSFSBZBAHARI-RUDMXATFSA-N
• Gene Information: human ... IMPDH1(3614) , IMPDH2(3615)

Description

General description

Mycophenolic acid is an active metabolite of the ester prodrug mycophenolate mofetil (MPM), which is prescribed as an immunosuppressant to prevent the organ transplantation rejection and also in the treatment of certain autoimmune diseases.

Application

Mycophenolic acid (MPA), produced by Penicillum brevi-compactum, is a selective inhibitor of inosine monphosphate dehydrogenase, thus inhibiting DNA synthesis in T and B lymphocytes. It has also been shown to act as an immunosuppressive agent, and as an inducer of monocyte differentiation and apoptosis in human lymphoid and monocytic cell lines. As a selection agent, MPA is used for transfected animal cells expressing the E. Coli gene for xanthine-guanine phosphoribosyl transferase, and is recommended for use at 25μg/mL.

Mycophenolic acid may be used as a reference standard for the determination of the analyte in human plasma by ultra-performance liquid chromatography tandem mass spectrometry.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Mode of Action: This product acts by suppressing the cytokine-induced nitric oxide production, inhibiting early stage biosynthesis of purine nucleotides and as a specific inhibitor of IMP dehydrogenase.

Caution

As supplied, this product should be stored desiccated at 2-8°C, and is stable for 5 years when stored properly.

Preparation Note

Mycophenolic acid is soluble in methanol at 50 mg/mL, yielding a colorless to faint yellow solution, as well as chloroform, dichloromethane, ethanol and .1 N NaOH. After reconstitution, the recommendation is to sterilize via filtration thorugh a 0.22 μm pore-size filter, aliquot, and freeze at -20°C.

Safety Information

• Pictograms: GHS07,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H302 - H341 - H360D - H372 - H410
• Precautionary Statements: P202 - P260 - P264 - P273 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Muta. 2 - Repr. 1B - STOT RE 1 Oral
• Target Organs: Immune system
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable