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Merck

M5255

Mycophenolic acid

from Penicillium brevicompactum, ≥98% (HPLC), powder, IMP dehydrogenase inhibitor

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
NACRES:
NA.77
PubChem Substance ID:
24896987
UNSPSC Code:
12352106
EC Number:
246-119-3
MDL number:
MFCD00036814
Beilstein/REAXYS Number:
1295848

Product Name

Mycophenolic acid, ≥98%

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

biological source

Penicillium brevicompactum

assay

≥98%

color

white to yellow-white

mp

<143.0 °C

solubility

methanol: 49.00-51.00 mg/mL, clear, colorless to faintly yellow

mode of action

enzyme | inhibits

originator

Novartis

storage temp.

2-8°C

Quality Level

300

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.

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.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000445541
0000445541
0000359869
0000359869
0000246560

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Guste Urbonaite et al.
Communications biology, 4(1), 822-822 (2021-07-02)
Stochastic gene expression leads to inherent variability in expression outcomes even in isogenic single-celled organisms grown in the same environment. The Drop-Seq technology facilitates transcriptomic studies of individual mammalian cells, and it has had transformative effects on the characterization of
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
Amy Tarangelo et al.
Life science alliance, 5(4) (2022-01-26)
Nucleotide synthesis is a metabolically demanding process essential for DNA replication and other processes in the cell. Several anticancer drugs that inhibit nucleotide metabolism induce apoptosis. How inhibition of nucleotide metabolism impacts non-apoptotic cell death is less clear. Here, we
Natacha S Ogando et al.
Transplant international : official journal of the European Society for Organ Transplantation, 35, 10369-10369 (2022-07-12)
Kidney transplant recipients (KTRs) are at increased risk for a more severe course of COVID-19, due to their pre-existing comorbidity and immunosuppression. Consensus protocols recommend lowering immunosuppression in KTRs with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection, but the
Christine E Staatz et al.
Clinical pharmacokinetics, 50(12), 759-772 (2011-11-18)
This review seeks to summarize the available data about Bayesian estimation of area under the plasma concentration-time curve (AUC) and dosage prediction for mycophenolic acid (MPA) and evaluate whether sufficient evidence is available for routine use of Bayesian dosage prediction
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Data Sheet - M5255

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