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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C17H20O6
CAS Number:
24280-93-1
Molecular Weight:
320.34
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329769720
EC Number:
246-119-3
Beilstein/REAXYS Number:
1295848
MDL number:
MFCD00036814

Product Name

Mycophenolic acid, analytical standard

InChI key

HPNSFSBZBAHARI-RUDMXATFSA-N

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+

SMILES string

COc1c(C)c2COC(=O)c2c(O)c1C\C=C(/C)CCC(O)=O

grade

analytical standard

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

Quality Level

100

Gene Information

human ... IMPDH1(3614), IMPDH2(3615)

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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.

Disclaimer

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

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.

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.

signalword

Danger

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4425
BCCM3130
BCCH1901
BCCH6435
BCCF8963

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LC- MS/MS method for quantitation of mycophenolic acid, mycophenolic acid acyl-glucuronide, and 7-O-mycophenolic acid glucuronide in serum.
Merrigan SD, et al.
Clinical mass spectrometry, 3, 41- 48 (2017)
Determination of mycophenolic acid in human plasma by ultra performance liquid chromatography tandem mass spectrometry.
Upadhyay V, et al.
Journal of Pharmaceutical Analysis, 4(3), 205- 216 (2014)
Burkhard Tönshoff et al.
Transplantation reviews (Orlando, Fla.), 25(2), 78-89 (2011-04-02)
Mycophenolate mofetil (MMF) is widely used for maintenance immunosuppressive therapy in pediatric renal and heart transplant recipients. Children undergo developmental changes (ontogeny) of drug disposition, which may affect drug metabolism of the active compound mycophenolic acid (MPA). Therefore, a detailed
Hylke de Jonge et al.
Therapeutic drug monitoring, 31(4), 416-435 (2009-06-19)
Although therapeutic drug monitoring (TDM) of immunosuppressive drugs has been an integral part of routine clinical practice in solid organ transplantation for many years, ongoing research in the field of immunosuppressive drug metabolism, pharmacokinetics, pharmacogenetics, pharmacodynamics, and clinical TDM keeps
Neal M Davies et al.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 22(9), 2440-2448 (2007-06-15)
Patient and graft survival following renal transplantation have improved markedly over the past decade, meaning that physician attention has turned more towards minimizing short- and long-term toxicities associated with immunosuppressive regimens. Gastrointestinal (GI) adverse events are common following renal transplantation
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