Propylthiouracil

Identification

Summary

Propylthiouracil is a thiourea antithyroid agent used to treat hyperthyroidism.

Generic Name
Propylthiouracil
DrugBank Accession Number
DB00550
Background

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)

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 170.232
Monoisotopic: 170.051383642
Chemical Formula
C7H10N2OS
Synonyms
  • 2-Mercapto-6-propyl-4-pyrimidone
  • 2-Mercapto-6-propylpyrimid-4-one
  • 2-Thio-4-oxo-6-propyl-1,3-pyrimidine
  • 2-Thio-6-propyl-1,3-pyrimidin-4-one
  • 4-propyl-2-thiouracil
  • 6-Propyl-2-thio-2,4(1H,3H)pyrimidinedione
  • 6-propyl-2-thiouracil
  • 6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
  • 6-Propylthiouracil
  • 6-Thio-4-propyluracil
  • Propiltiouracilo
  • Propylthiouracil
  • Propylthiouracile
  • Propylthiouracilum
External IDs
  • NSC-6498
  • NSC-70461

Pharmacology

Indication

Used to manage hyperthyroidism which is due to an overactive thyroid gland (Grave's disease).

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofHyperthyroidism••••••••••••
Management ofHyperthyroidism••••••••••••
Management ofHyperthyroidism•••••••••••••••••••••• ••••••••••• ••••••••• •••••••
Management ofHyperthyroidism•••••••••••••••••••••• ••••••••••• ••••••••• •••••••
Management ofThyrotoxic crisis••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Propylthiouracil is a thiourea antithyroid agent. Grave's disease is the most common cause of hyperthyroidism. It is an autoimmune disease where an individual's own antibodies attach to thyroid stimulating hormone receptors within cells of the thyroid gland and then trigger overproduction of thyroid hormone. The two thyroid hormones manufactured by the thyroid gland, thyroxine (T4) and triiodothyronine (T3), are formed by combining iodine and a protein called thyroglobulin with the assistance of an enzyme called peroxidase. PTU inhibits iodine and peroxidase from their normal interactions with thyroglobulin to form T4 and T3. This action decreases thyroid hormone production. PTU also interferes with the conversion of T4 to T3, and, since T3 is more potent than T4, this also reduces the activity of thyroid hormones. The actions and use of propylthiouracil are similar to those of methimazole.

Mechanism of action

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.

TargetActionsOrganism
AThyroid peroxidase
inhibitor
Humans
Absorption

Well absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

82%

Metabolism
Not Available
Route 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

Clearance

Not Available

Adverse Effects
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Toxicity

Oral, rat: LD50 = 1250 mg/kg.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Propylthiouracil is combined with Abatacept.
AbciximabPropylthiouracil may increase the anticoagulant activities of Abciximab.
AcalabrutinibThe therapeutic efficacy of Propylthiouracil can be decreased when used in combination with Acalabrutinib.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Propylthiouracil.
AcenocoumarolPropylthiouracil may increase the anticoagulant activities of Acenocoumarol.
Food Interactions
  • Take at the same time every day.

Products

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Product Images
International/Other Brands
Antiroid (Bu Kwang) / Propil (Pfizer) / Propilracil (Biolab) / Propycil (Admeda) / Proracyl (Genopharm) / Prothiucil (Phafag) / Prothuril (Uni-Pharma) / PTU (Alkaloid) / Thiuragyl (Tanabe Mitsubishi Pharma) / Thyrosan (Sun-Farm) / Tiotil (Nevada Pharma) / Tirostat (Metlen) / Uracil (Pharmasant)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HalycilTablet50 mgOralHalewood Chemicals Limited2022-03-23Not applicableCanada flag
Propyl-thyracilTablet100 mgOralPaladin Labs Inc.1945-12-312020-04-07Canada flag
Propyl-thyracilTablet50 mgOralPaladin Labs Inc.1951-12-312020-03-05Canada flag
PropylthiouracilTablet50 mg/1OralAmerican Health Packaging2015-09-15Not applicableUS flag
PropylthiouracilTablet50 mg/1OralClinical Solutions Wholsesale2010-01-292017-06-26US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-propylthiouracilTablet50 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-propylthiouracilTablet100 mgOralApotex CorporationNot applicableNot applicableCanada flag
PMS-propylthiouracilTablet50 mgOralPharmascience IncNot applicableNot applicableCanada flag
PMS-propylthiouracilTablet100 mgOralPharmascience IncNot applicableNot applicableCanada flag
PropylthiouracilTablet50 mg/1OralCardinal Health1982-01-012013-04-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CIPROFLOXACINA 0.3% + DEXAMETASONA 0.1% SUSPENSIÓN OFTÁLMICAPropylthiouracil (3 mg) + Dexamethasone (1 mg)SuspensionOphthalmicOPHARM LTDA.2022-05-02Not applicableColombia flag

Categories

ATC Codes
H03BA02 — Propylthiouracil
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Pyrimidinethiones / 2-Thiopyrimidines / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Thioureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
2-thiopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidinethione (CHEBI:8502) / a small molecule (CPD-11429)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
721M9407IY
CAS number
51-52-5
InChI Key
KNAHARQHSZJURB-UHFFFAOYSA-N
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)
IUPAC Name
6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
SMILES
CCCC1=CC(=O)NC(=S)N1

References

General References
Not Available
Human Metabolome Database
HMDB0014690
KEGG Drug
D00562
KEGG Compound
C07569
PubChem Compound
657298
PubChem Substance
46505181
ChemSpider
571424
BindingDB
50133597
RxNav
8794
ChEBI
8502
ChEMBL
CHEMBL1518
ZINC
ZINC000004640636
Therapeutic Targets Database
DAP001247
PharmGKB
PA451156
PDBe Ligand
3CJ
Drugs.com
Drugs.com Drug Page
Wikipedia
Propylthiouracil
PDB Entries
5hpw
MSDS
Download (53.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentThyroid Eye Disease1
3CompletedTreatmentAtherosclerosis of Artery / Graves' Disease / Hyperthyroidism / Pathophysiology1
3CompletedTreatmentBreast Cancer2
3CompletedTreatmentColorectal Cancer3
3CompletedTreatmentGastric Cancer1

Pharmacoeconomics

Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Actavis elizabeth llc
  • Anabolic inc
  • Dava pharmaceuticals inc
  • Halsey drug co inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lannett co inc
  • Eli lilly and co
  • Mutual pharmaceutical co inc
  • L perrigo co
  • Tablicaps inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
Packagers
  • Actavis Group
  • Avkare Incorporated
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Remedy Repack
  • Shanghai Multi Med Union Co. Ltd.
  • Tya Pharmaceuticals
  • Vangard Labs Inc.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
SuspensionOphthalmic
SolutionConjunctival; Ophthalmic3 mg
SolutionOphthalmic3 mg
TabletOral250 mg
TabletOral50 mg
TabletOral100 mg
TabletOral50 mg/1
TabletOral
Prices
Unit descriptionCostUnit
Propyl-Thyracil 100 mg Tablet0.34USD tablet
Propyl-Thyracil 50 mg Tablet0.22USD tablet
Propylthiouracil 50 mg tablet0.18USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)219 °CPhysProp
water solubility1200 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.4Not Available
logS-2.15ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.466 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity48.9 m3·mol-1Chemaxon
Polarizability17.79 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.9045
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5812
P-glycoprotein inhibitor INon-inhibitor0.8141
P-glycoprotein inhibitor IINon-inhibitor0.9753
Renal organic cation transporterNon-inhibitor0.8407
CYP450 2C9 substrateNon-substrate0.6573
CYP450 2D6 substrateNon-substrate0.7926
CYP450 3A4 substrateNon-substrate0.6664
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9259
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.81
CarcinogenicityNon-carcinogens0.9396
BiodegradationNot ready biodegradable0.9643
Rat acute toxicity2.1786 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9769
hERG inhibition (predictor II)Non-inhibitor0.8423
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.33 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-3900000000-31cf32b92bb0613f3864
Mass Spectrum (Electron Ionization)MSsplash10-00dl-9800000000-dd34c50b7aa55979d5f2
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-0900000000-6549521c2c4645bc9542
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-f857bb6ee86a6e7b0ab3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-066r-7900000000-e5e5c265147935fdd8d2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-927304e1ff32407a8d18
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-343c26fd83ebb89d346d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-0d1467a930d2ddf9349b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-0b376a1be2d2d48ad875
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0900000000-f095bd0fa6c365161ec9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-2ce23fa0cb6ec6129e29
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-9ee3b1971c716e9a4dc1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-7d9cf3791e4e7800916d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ik9-5900000000-41be31a4c739b4ea29a4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03xr-9200000000-8eb9b68ae97914399fc0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-1900000000-b867c06c7c74b627274c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0900000000-6549521c2c4645bc9542
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-98761f2a554448cd02ef
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-5900000000-5842ac6566cd201a4496
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0h3j-5900000000-ad07a9e2482c8bf1fc61
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-1ab15464f642d5535d94
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-57df79e5b0a2f703c1fc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9600000000-bd72fa64bd6ee457a518
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-139.0440939
predicted
DarkChem Lite v0.1.0
[M-H]-139.1663939
predicted
DarkChem Lite v0.1.0
[M-H]-139.1361939
predicted
DarkChem Lite v0.1.0
[M-H]-134.90526
predicted
DeepCCS 1.0 (2019)
[M+H]+140.5030939
predicted
DarkChem Lite v0.1.0
[M+H]+139.8440939
predicted
DarkChem Lite v0.1.0
[M+H]+140.4225939
predicted
DarkChem Lite v0.1.0
[M+H]+138.13158
predicted
DeepCCS 1.0 (2019)
[M+Na]+139.6854939
predicted
DarkChem Lite v0.1.0
[M+Na]+139.6364939
predicted
DarkChem Lite v0.1.0
[M+Na]+139.8133939
predicted
DarkChem Lite v0.1.0
[M+Na]+147.27414
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peroxidase activity
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
Uniprot Name
Thyroid peroxidase
Molecular Weight
102961.63 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
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 o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
L-ascorbic acid binding
Specific Function
Conversion of dopamine to noradrenaline.
Gene Name
DBH
Uniprot ID
P09172
Uniprot Name
Dopamine beta-hydroxylase
Molecular Weight
69064.45 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Wang WD, Wang Y, Wen HJ, Buhler DR, Hu CH: Phenylthiourea as a weak activator of aryl hydrocarbon receptor inhibiting 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced CYP1A1 transcription in zebrafish embryo. Biochem Pharmacol. 2004 Jul 1;68(1):63-71. doi: 10.1016/j.bcp.2004.03.010. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 29, 2024 03:23