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Supelco

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
Beilstein/REAXYS Number:
1295848
EC Number:
246-119-3
MDL number:
MFCD00036814
UNSPSC Code:
41116107
PubChem Substance ID:
329769720
NACRES:
NA.24

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)

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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.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

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USP

USP

1448978

Mycophenolate Mofetil Related Compound B

Sigma-Aldrich

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Citrinin from Penicillium citrinum, ≥98% (HPLC)

Sigma-Aldrich

C1017

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Griseofulvin from Penicillium griseofulvum, 97.0-102.0%

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Cyclopiazonic acid from Penicillium cyclopium ≥98% (HPLC), powder

Sigma-Aldrich

C1530

Cyclopiazonic acid from Penicillium cyclopium

Ochratoxin A from Petromyces albertensis, ≥98% (HPLC)

Sigma-Aldrich

O1877

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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)
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)
Nicole K Bruchet et al.
Expert opinion on drug metabolism & toxicology, 5(9), 1079-1097 (2009-08-20)
Mycophenolic acid (MPA) is the active metabolite of mycophenolate mofetil, a widely used immunosuppressant. Numerous studies have developed limited sampling strategies (LSSs) to predict MPA AUC in solid organ transplant recipients. To systematically review and assess quality of literature pertaining
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
Use of mycophenolic acid in non-transplant renal diseases.
Patricia M Stassen et al.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 22(4), 1013-1019 (2007-02-20)
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