A modulator of utrophin production
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Ezutromid

Item No. 20309

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(ethylsulfonyl)-2-(2-naphthalenyl)-benzoxazole
CAS Number
945531-77-1
Synonyms
  • BMN 195
  • SMT-C1100
  • VOX-C1100
Molecular Formula
C19H15NO3S
Formula Weight
337.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 3 mg/mlDMSO:PBS(pH 7.2) (1:2): 0.3 mg/ml
λmax
236, 255, 262, 314 nm
SMILES
CCS(C1=CC=C2C(N=C(C3=CC(C=CC=C4)=C4C=C3)O2)=C1)(=O)=O
InChi Code
InChI=1S/C19H15NO3S/c1-2-24(21,22)16-9-10-18-17(12-16)20-19(23-18)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,2H2,1H3
InChi Key
KSGCNXAZROJSNW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

    $138

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    25 mg

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    Product Description

    Ezutromid is a modulator of utrophin production.1 It upregulates utrophin production in mouse myoblasts (EC50 = 0.91 µM in a reporter assay).2 It inhibits the activity of the cytochrome P450 (CYP) isoform CYP1A2 in pooled human liver microsomes (IC50 = 5.4 µM).3 Chronic administration of ezutromid (50 mg/kg) increases utrophin protein levels in the heart, increases grip strength, and decreases fatigue, indicated by distance traveled during forced exercise, in the mdx mouse model of muscular dystrophy.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tinsley, J.M., Fairclough, R.J., Storer, R., et al. Daily treatment with SMTC1100, a novel small molecule utrophin upregulator, dramatically reduces the dystrophic symptoms in the mdx mouse. PLoS One 6(5), e19189 (2011).

    2. Chancellor, D.R., Davies, K.E., De Moor, O., et al. Discovery of 2-arylbenzoxazoles as upregulators of utrophin production for the treatment of Duchenne muscular dystrophy. J. Med. Chem. 54(9), 3241-3250 (2011).

    3. Chatzopoulou, M., Claridge, T.D.W., Davies, K.E., et al. Isolation, structural identification, synthesis, and pharmacological profiling of 1,2- trans-dihydro-1,2-diol metabolites of the utrophin modulator ezutromid. J. Med. Chem. 63(5), 2547-2556 (2020).