Propylthiouracil (CHEM003670)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-09-11 02:06:03 UTC
Update Date2026-03-25 19:14:13 UTC
Accession NumberCHEM003670
Identification
Common NamePropylthiouracil
ClassSmall Molecule
DescriptionPropylthiouracil is only found in individuals that have used or taken this drug. It is a thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. Propylthiouracil binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (3) and tri-iodothyronine (2), which are the main hormones produced by the thyroid gland. Therefore propylthiouracil effectively inhibits the production of new thyroid hormones.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Antimetabolite
  • Antithyroid Agent
  • Drug
  • Ester
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinoneChEBI
2-Mercapto-6-propyl-4-pyrimidoneChEBI
2-Mercapto-6-propylpyrimid-4-oneChEBI
2-Thio-4-oxo-6-propyl-1,3-pyrimidineChEBI
2-Thio-6-propyl-1,3-pyrimidin-4-oneChEBI
4-Propyl-2-thiouracilChEBI
6-Propyl-2-thio-2,4(1H,3H)pyrimidinedioneChEBI
6-Propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneChEBI
6-PropylthiouracilChEBI
6-Thio-4-propyluracilChEBI
PropiltiouraciloChEBI
PropylthiouracileChEBI
PropylthiouracilumChEBI
ProcasilHMDB
PropacilHMDB
PropilthiouracilHMDB
PropycilHMDB
Propyl-thioristHMDB
Propyl-thioritHMDB
Propyl-thyracilHMDB
PropylthioritHMDB
PropythiouracilHMDB
ProthiucilHMDB
ProthiuroneHMDB
ProthycilHMDB
ProthyranHMDB
ProtiuralHMDB
ThiuragylHMDB
6-Propyl-2-thiouracilHMDB
6 Propyl 2 thiouracilHMDB
PropylthiouracilChEBI
Chemical FormulaC7H10N2OS
Average Molecular Mass170.232 g/mol
Monoisotopic Mass170.051 g/mol
CAS Registry Number51-52-5
IUPAC Name6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
Traditional Namepropylthiouracil
SMILESCCCC1=CC(=O)NC(=S)N1
InChI IdentifierInChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
InChI KeyKNAHARQHSZJURB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • 2-thiopyrimidine
  • Pyrimidinethione
  • Thiopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Thiourea
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point219°C
Boiling PointNot Available
Solubility1200 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.53ALOGPS
logP1.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.09ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.9 m³·mol⁻¹ChemAxon
Polarizability17.79 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3900000000-31cf32b92bb0613f3864Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0900000000-6549521c2c4645bc9542Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f857bb6ee86a6e7b0ab3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-7900000000-e5e5c265147935fdd8d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-927304e1ff32407a8d18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-343c26fd83ebb89d346dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0d1467a930d2ddf9349bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-0b376a1be2d2d48ad875Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fk9-0900000000-f095bd0fa6c365161ec9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-2ce23fa0cb6ec6129e29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-9ee3b1971c716e9a4dc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-7d9cf3791e4e7800916dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-5900000000-41be31a4c739b4ea29a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-9200000000-8eb9b68ae97914399fc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-1900000000-b867c06c7c74b627274cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-6549521c2c4645bc9542Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-9300000000-1c45f7c8a1ed2bb4ff1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-9000000000-316f99d9fa451f830eccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-9300000000-6e8260b8f96483c7a725Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-9000000000-acdbd4788bf0a434a52cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-c92d3e54c5a5d44238b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2900000000-02a40d3cf3fcf7117143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9100000000-d83421a35456bb2cd516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-0171c0c7c9c5fd9b0d23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066u-9700000000-e296fd0e7563b2f97dd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-74e2c284c39ca64e90d4Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-dd34c50b7aa55979d5f2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureWell absorbed following oral administration.
Mechanism of ToxicityPropylthiouracil binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (3) and tri-iodothyronine (2), which are the main hormones produced by the thyroid gland. Therefore propylthiouracil effectively inhibits the production of new thyroid hormones.
MetabolismRoute of Elimination: Propylthiouracil is readily absorbed and is extensively metabolized. Approximately 35% of the drug is excreted in the urine, in intact and conjugated forms, within 24 hours. Half Life: 2 hours
Toxicity ValuesOral, rat: LD50 = 1250 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesUsed to manage hyperthyroidism which is due to an overactive thyroid gland (Grave's disease).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00550
HMDB IDHMDB0014690
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropylthiouracil
Chemspider ID571424
ChEBI ID8502
PubChem Compound ID657298
Kegg Compound IDC07569
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11005705
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11036881
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11350963
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11401533
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12135875
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12922945
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14692727
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=14745920
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16380675
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16498810
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16880639
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17365943
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17497002
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17878268
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18055877
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=18710353
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=19530273
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=19578601
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=20166204
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21749382
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=6387489