An inhibitor of CDK/cyclin complexes and GSK3β
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(S)-PHA-533533

Item No. 45337

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(5-cyclopropyl-1H-pyrazol-3-yl)-αS-methyl-4-(2-oxo-1-pyrrolidinyl)-benzeneacetamide
CAS Number
437982-89-3
Molecular Formula
C19H22N4O2
Formula Weight
338.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile:Water (1:1): Slightly soluble: 0.1-1 mg/mlDMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C(CCC1)N1C2=CC=C([C@@H](C(NC3=NNC(C4CC4)=C3)=O)C)C=C2
InChi Code
InChI=1S/C19H22N4O2/c1-12(19(25)20-17-11-16(21-22-17)14-4-5-14)13-6-8-15(9-7-13)23-10-2-3-18(23)24/h6-9,11-12,14H,2-5,10H2,1H3,(H2,20,21,22,25)/t12-/m0/s1
InChi Key
UAOIPNOTWOYAMU-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $99

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    1 mg

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    5 mg

    $371

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    10 mg

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    Product Description

    (S)-PHA-533533 is an inhibitor of cyclin-dependent kinase 2 (Cdk2)/cyclin A, Cdk2/cyclin E, Cdk5/p25, and Cdk1/cyclin B complexes and glycogen synthase kinase 3β (GSK3β; IC50s = 37, 55, 65, 208, and 732 nM, respectively, in cell-free assays).1 It selectively inhibits these complexes and GSK3β over the Cdk4/cyclin D1 complex and a panel of 29 other kinases at 10 µM. (S)-PHA-533533 inhibits the growth of A2780 ovarian, HT-29 human colon, and HCT116 colorectal cancer cells (IC50s = 744, 639, and 1,354 nM, respectively) and induces cell cycle arrest at the G0/G1 phase in HT-29 cells. It reduces tumor growth in an A2780 mouse xenograft model when administered at a dose of 7.5 mg/kg. (S)-PHA-533533 also restores the expression of paternal UBE3A mRNA in a mouse model of Angelman syndrome.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pevarello, P., Brasca, M.G., Orsini, P., et al. 3-Aminopyrazole inhibitors of CDK2/cyclin A as antitumor agents. 2. Lead optimization. J. Med. Chem. 48(8), 2944-2956 (2005).

    2. Vihma, H., Li, K., Welton-Arndt, A., et al. Ube3a unsilencer for the potential treatment of Angelman syndrome. Nat. Commun. 15(1), 5558 (2024).