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Isolation, structural identification, synthesis, and pharmacological profiling of 1,2-trans-dihydro-1,2-diol metabolites of the utrophin modulator ezutromid

Abstract:

5-(Ethylsulfonyl)-2-(naphthalen-2-yl)benzo[d]oxazole (ezutromid, 1) is a first-in-class utrophin modulator that has been evaluated in a phase 2 clinical study for the treatment of Duchenne muscular dystrophy (DMD). Ezutromid was found to undergo hepatic oxidation of its 2-naphthyl substituent to produce two regioisomeric 1,2-dihydronaphthalene-1,2-diols, DHD1 and DHD3, as the major metabolites after oral administration in humans and rodents. In many patients, plasma levels of the DHD metaboli...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.jmedchem.9b01547

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Institution:
University of Oxford
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0003-1886-7705
More by this author
Institution:
University of Oxford
Department:
Chemistry
Role:
Author
ORCID:
0000-0001-5583-6460
More by this author
Institution:
University of Oxford
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
ORCID:
0000-0003-3181-8748
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Publisher:
American Chemical Society Publisher's website
Journal:
Journal of Medicinal Chemistry Journal website
Volume:
63
Issue:
5
Pages:
2547-2556
Publication date:
2019-10-10
DOI:
EISSN:
1520-4804
ISSN:
0022-2623
Pmid:
31599580
Source identifiers:
1061696
Language:
English
Keywords:
Pubs id:
pubs:1061696
UUID:
uuid:0c130b25-6efe-4eac-8cc7-497f6bfbd019
Local pid:
pubs:1061696
Deposit date:
2020-01-17

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