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Merck
CN

506154

Pifithrin-α, p-Nitro, Cyclic

A cell-permeable p53 inhibitor that exhibits 10-fold higher potency and 50% longer half-life than Pifithrin-α.

Synonym(s):

Pifithrin-α, p-Nitro, Cyclic, 2-(4-Nitrophenyl)imidazo[2,1-b]-5,6,7,8-tetrahydrobenzothiazole

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About This Item

Empirical Formula (Hill Notation):
C15H13N3O2S
CAS Number:
60477-38-5
Molecular Weight:
299.35
MDL number:
MFCD05670249
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Pifithrin-α, p-Nitro, Cyclic, A cell-permeable p53 inhibitor that exhibits 10-fold higher potency and 50% longer half-life than Pifithrin-α.

InChI key

XMFNSEDROOHGBY-UHFFFAOYSA-N

InChI

1S/C15H13N3O2S/c19-18(20)11-7-5-10(6-8-11)12-9-17-13-3-1-2-4-14(13)21-15(17)16-12/h5-9H,1-4H2

SMILES string

[s]1c2[n](c4c1CCCC4)cc(n2)c3ccc(cc3)[N+](=O)[O-]

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: 2.5 mg/mL
ethanol: 250 μg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
ED50 = 30 nM in protecting etoposide-induced cortical neuron death
Primary Target
p53
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Standard Handling (A)

General description

A cell-permeable p53 inhibitor that exhibits 10-fold higher potency (ED50 = 30 nM in protecting etoposide-induced cortical neuron death) and 50% longer half-life (t1/2 = 6h in neuron culture medium at 37°C) than Pifithrin-α (Cat. No. 506132). However, despite its in vitro efficacy, this inhibitor is not effective when adminstered in rats in vivo. For in vivo applications, please consider Pifithrin-α, p-Nitro (Cat. No. 506152).

Other Notes

Pietrancosta, N., et al. 2006. J. Med. Chem.49, 3645.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Richard A Zager et al.
American journal of physiology. Renal physiology, 316(4), F674-F681 (2019-01-31)
The cyclin kinase inhibitor p21 is acutely upregulated during acute kidney injury (AKI) and exerts cytoprotective effects. A proposed mechanism is oxidant stress-induced activation of p53, the dominant p21 transcription factor. Glycerol-induced rhabdomyolysis induces profound renal oxidant stress. Hence, we

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