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)
1. Bufe B, Breslin PA, Kuhn C, Reed DR, Tharp CD, Slack JP, Kim UK, Drayna D, Meyerhof W. (2005)
The molecular basis of individual differences in phenylthiocarbamide and propylthiouracil bitterness perception.
Curr Biol, 15 (4): 322-7. [PMID:15723792]
2. Nakashima T, Taurog A, Riesco G. (1978)
Mechanism of action of thioureylene antithyroid drugs: factors affecting intrathyroidal metabolism of propylthiouracil and methimazole in rats.
Endocrinology, 103 (6): 2187-97. [PMID:748042]