propylthiouracil   Click here for help

GtoPdb Ligand ID: 6650

Synonyms: Thyreostat®
Approved drug PDB Ligand
propylthiouracil is an approved drug (FDA (1947))
Compound class: Synthetic organic
Comment: Propylthiouracil is a thiouracil-derived drug, which acts as a thyroperoxidase inhibitor.
Propylthiouracil is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 80.74
Molecular weight 170.05
XLogP 1.85
No. Lipinski's rules broken 0
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Canonical SMILES CCCc1cc(=O)[nH]c(=S)[nH]1
Isomeric SMILES CCCc1cc(=O)[nH]c(=S)[nH]1
InChI InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
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Summary of Clinical Use Click here for help
Used in the treatment of Grave's disease.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibits thyroid peroxidase and thereby the conversion by this enzyme of iodide to iodine, and the incorporation of the iodine molecule onto the phenol rings to tyrosine found in thyroglobulin. As thryroglobulin is normally degraded to produce thyroxine and tri-iodothyronine, propylthiouracil inhibits the production of new thyroid hormones.
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