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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:32 UTC
HMDB IDHMDB14690
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropylthiouracil
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. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534)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 (T4) and tri-iodothyronine (T3), which are the main hormones produced by the thyroid gland. Therefore propylthiouracil effectively inhibits the production of new thyroid hormones.
Structure
Thumb
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
Chemical FormulaC7H10N2OS
Average Molecular Weight170.232
Monoisotopic Molecular Weight170.051383642
IUPAC Name6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
Traditional Namepropylthiouracil
CAS Registry Number51-52-5
SMILES
CCCC1=CC(=O)NC(=S)N1
InChI Identifier
InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
InChI KeyInChIKey=KNAHARQHSZJURB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidones. These 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
  • Pyrimidone
  • Pyrimidinethione
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Thiourea
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antimetabolites
  • Antithyroid Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.66e-01 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 mg/mLALOGPS
logP1.53ALOGPS
logP1.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.09ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.9 m3·mol-1ChemAxon
Polarizability17.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-00dl-9800000000-dd34c50b7aa55979d5f2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00550
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00550
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00550
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID571424
KEGG Compound IDC07569
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropylthiouracil
NuGOwiki LinkHMDB14690
Metagene LinkHMDB14690
METLIN IDNot Available
PubChem Compound657298
PDB IDNot Available
ChEBI ID8502
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
References
  1. Hidaka H, Nagasaka A: Inhibition of dopamine beta-hydroxylase by anti-thyroid agents, methimazole and propylthiouracil. Biochem Pharmacol. 1977 Jun 1;26(11):1092-3. [880264 ]
General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
References
  1. Sugawara M, Sugawara Y, Wen K: Methimazole and propylthiouracil increase cellular thyroid peroxidase activity and thyroid peroxidase mRNA in cultured porcine thyroid follicles. Thyroid. 1999 May;9(5):513-8. [10365684 ]
  2. Manzon RG, Holmes JA, Youson JH: Variable effects of goitrogens in inducing precocious metamorphosis in sea lampreys (Petromyzon marinus). J Exp Zool. 2001 Apr 15;289(5):290-303. [11241400 ]
  3. Ferreira AC, de Carvalho Cardoso L, Rosenthal D, de Carvalho DP: Thyroid Ca2+/NADPH-dependent H2O2 generation is partially inhibited by propylthiouracil and methimazole. Eur J Biochem. 2003 Jun;270(11):2363-8. [12755690 ]
  4. Schmutzler C, Bacinski A, Gotthardt I, Huhne K, Ambrugger P, Klammer H, Schlecht C, Hoang-Vu C, Gruters A, Wuttke W, Jarry H, Kohrle J: The ultraviolet filter benzophenone 2 interferes with the thyroid hormone axis in rats and is a potent in vitro inhibitor of human recombinant thyroid peroxidase. Endocrinology. 2007 Jun;148(6):2835-44. Epub 2007 Mar 22. [17379648 ]
  5. Taurog A, Dorris ML: A reexamination of the proposed inactivation of thyroid peroxidase in the rat thyroid by propylthiouracil. Endocrinology. 1989 Jun;124(6):3038-42. [2656250 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Lee E, Miki Y, Katsura H, Kariya K: Mechanism of inactivation of myeloperoxidase by propylthiouracil. Biochem Pharmacol. 1990 May 1;39(9):1467-71. [2159305 ]
  2. Kariya K, Lee E, Hirouchi M: Relationship between leukopenia and bone marrow myeloperoxidase in the rat treated with propylthiouracil. Jpn J Pharmacol. 1984 Oct;36(2):217-22. [6096612 ]
  3. Zhang AH, Chen M, Gao Y, Zhao MH, Wang HY: Inhibition of oxidation activity of myeloperoxidase (MPO) by propylthiouracil (PTU) and anti-MPO antibodies from patients with PTU-induced vasculitis. Clin Immunol. 2007 Feb;122(2):187-93. Epub 2006 Oct 27. [17070108 ]
  4. Lee E, Hirouchi M, Hosokawa M, Sayo H, Kohno M, Kariya K: Inactivation of peroxidases of rat bone marrow by repeated administration of propylthiouracil is accompanied by a change in the heme structure. Biochem Pharmacol. 1988 Jun 1;37(11):2151-3. [2837228 ]