PROPYLTHIOURACIL

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Search structure


Trade Names	PROPYLTHIOURACIL
Synonyms	NSC-6498 NSC-70461 Propacil Propylthiouracil Prothyran Thyreostat Thyreostat ii
Status
Molecule Category	Free-form
ATC	H03BA02
UNII	721M9407IY
EPA CompTox	DTXSID5021209


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	KNAHARQHSZJURB-UHFFFAOYSA-N
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C7H10N2OS
Molecular Weight	170.24
AlogP	1.38
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	2.0
Polar Surface Area	48.65
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	11.0

Bioactivity

Mechanism of Action	Action	Reference
Thyroid peroxidase inhibitor	INHIBITOR	PubMed Wikipedia FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	2810-5700	-	-	29
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	80

Assay Description	Organism	Bioactivity	Reference
Inhibition of Human Placenta Inner-Ring Iodothyronine 5-deiodinase at the compound concentration of 5 mM	None	29.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	79.91 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	90.71 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	17.4 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	8.71 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	16.2 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	12.96 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	26.31 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	3.22 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-1.39 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-2.42 %
Antithyroid activity in L-T4-induced Wistar albino rat model of hyperthyroidism assessed as reduction in T3 level at 10 mg/kg, po qd post 12 days of L-T4 challenge measured after 15 days in presence of [125I]-T3 by RIA	Rattus norvegicus	56.5 %
Antithyroid activity in L-T4-induced Wistar albino rat model of hyperthyroidism assessed as reduction in T4 level at 10 mg/kg, po qd post 12 days of L-T4 challenge measured after 15 days in presence of [125I]-T4 by RIA	Rattus norvegicus	81.0 %
Antithyroid activity in L-T4-induced Wistar albino rat model of hyperthyroidism assessed as inhibition of hepatic 5'-monodeiodinase 1 activity by measuring reduction in T3 level using T4 as substrate at 10 mg/kg, po qd post 12 days of L-T4 challenge measured after 15 days in presence of [125I]-T3 by RIA	Rattus norvegicus	59.0 %
Inhibition of N-terminal His6-tagged human Cyb5R3 expressed in Escherichia coli SoluBL21 assessed as reduction in NADH-ferricyanide reductase activity at 500 uM pre-incubated for 15 mins before addition of NADH and potassium ferricyanide by spectrophotometric assay relative to control	Homo sapiens	100.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	28.13 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.12 %

Cross References

Resources	Reference
ChEBI	8502
ChEMBL	CHEMBL1518
DrugBank	DB00550
DrugCentral	2308
FDA SRS	721M9407IY
Human Metabolome Database	HMDB0014690
Guide to Pharmacology	6650
KEGG	C07569
PDB	3CJ
PharmGKB	PA451156
PubChem	657298
SureChEMBL	SCHEMBL41239
ZINC	ZINC000004640636

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).