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
Structure for Propylthiouracil (DB00550)
- 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).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Hyperthyroidism •••••••••••• Management of Hyperthyroidism •••••••••••• Management of Hyperthyroidism •••••••••••• •••••••••• ••••••••••• ••••••••• ••••••• Management of Hyperthyroidism •••••••••••• •••••••••• ••••••••••• ••••••••• ••••••• Management of Thyrotoxic crisis ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AThyroid peroxidase inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral, rat: LD50 = 1250 mg/kg.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The risk or severity of adverse effects can be increased when Propylthiouracil is combined with Abatacept. Abciximab Propylthiouracil may increase the anticoagulant activities of Abciximab. Acalabrutinib The therapeutic efficacy of Propylthiouracil can be decreased when used in combination with Acalabrutinib. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Propylthiouracil. Acenocoumarol Propylthiouracil may increase the anticoagulant activities of Acenocoumarol. - Food Interactions
- Take at the same time every day.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Halycil Tablet 50 mg Oral Halewood Chemicals Limited 2022-03-23 Not applicable Canada 
Propyl-thyracil Tablet 100 mg Oral Paladin Labs Inc. 1945-12-31 2020-04-07 Canada Propyl-thyracil Tablet 50 mg Oral Paladin Labs Inc. 1951-12-31 2020-03-05 Canada Propylthiouracil Tablet 50 mg/1 Oral Physicians Total Care, Inc. 1996-02-01 2011-06-30 US 
Propylthiouracil Tablet 50 mg/1 Oral Par Pharmaceutical, Inc. 1947-07-28 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-propylthiouracil Tablet 100 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-propylthiouracil Tablet 50 mg Oral Apotex Corporation Not applicable Not applicable Canada PMS-propylthiouracil Tablet 100 mg Oral Pharmascience Inc Not applicable Not applicable Canada PMS-propylthiouracil Tablet 50 mg Oral Pharmascience Inc Not applicable Not applicable Canada Propylthiouracil Tablet 50 mg/1 Oral Hikma Pharmaceuticals USA Inc. 1971-07-23 2016-09-30 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CIPROFLOXACINA 0.3% + DEXAMETASONA 0.1% SUSPENSIÓN OFTÁLMICA Propylthiouracil (3 mg) + Dexamethasone (1 mg) Suspension Ophthalmic OPHARM LTDA. 2022-05-02 Not applicable Colombia 
Categories
- ATC Codes
- H03BA02 — Propylthiouracil
- Drug Categories
- Agents Causing Muscle Toxicity
- Antimetabolites
- Antithyroid agents
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Myelosuppressive Agents
- Noxae
- Pyrimidines
- Pyrimidinones
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Thiouracil
- Thiouracils
- Thyroid Hormone Synthesis Inhibitor
- Thyroid Hormone Synthesis Inhibitors
- Thyroid Products
- Toxic Actions
- 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
- External Links
- Human Metabolome Database
- HMDB0014690
- KEGG Drug
- D00562
- KEGG Compound
- C07569
- PubChem Compound
- 657298
- PubChem Substance
- 46505181
- ChemSpider
- 571424
- BindingDB
- 50133597
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Thyroid Eye Disease 1 3 Completed Treatment Atherosclerosis of Artery / Graves' Disease / Hyperthyroidism / Pathophysiology 1 3 Completed Treatment Breast Cancer 2 3 Completed Treatment Colorectal Cancer 3 3 Completed Treatment Gastric Cancer 1
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
Form Route Strength Suspension Ophthalmic Solution Conjunctival; Ophthalmic 3 mg Solution Ophthalmic 3 mg Tablet Oral 250 mg Tablet Oral 50 mg Tablet Oral 100 mg Tablet Oral 50 mg/1 Tablet Oral - Prices
Unit description Cost Unit Propyl-Thyracil 100 mg Tablet 0.34USD tablet Propyl-Thyracil 50 mg Tablet 0.22USD tablet Propylthiouracil 50 mg tablet 0.18USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 219 °C PhysProp water solubility 1200 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.4 Not Available logS -2.15 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.466 mg/mL ALOGPS logP 1.53 ALOGPS logP 1.2 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 8.09 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.13 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 48.9 m3·mol-1 Chemaxon Polarizability 17.79 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier + 0.9045 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5812 P-glycoprotein inhibitor I Non-inhibitor 0.8141 P-glycoprotein inhibitor II Non-inhibitor 0.9753 Renal organic cation transporter Non-inhibitor 0.8407 CYP450 2C9 substrate Non-substrate 0.6573 CYP450 2D6 substrate Non-substrate 0.7926 CYP450 3A4 substrate Non-substrate 0.6664 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9259 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.81 Carcinogenicity Non-carcinogens 0.9396 Biodegradation Not ready biodegradable 0.9643 Rat acute toxicity 2.1786 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9769 hERG inhibition (predictor II) Non-inhibitor 0.8423
Spectra
- Mass Spec (NIST)
- Download (9.33 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.0440939 predictedDarkChem Lite v0.1.0 [M-H]- 139.1663939 predictedDarkChem Lite v0.1.0 [M-H]- 139.1361939 predictedDarkChem Lite v0.1.0 [M-H]- 134.90526 predictedDeepCCS 1.0 (2019) [M+H]+ 140.5030939 predictedDarkChem Lite v0.1.0 [M+H]+ 139.8440939 predictedDarkChem Lite v0.1.0 [M+H]+ 140.4225939 predictedDarkChem Lite v0.1.0 [M+H]+ 138.13158 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.6854939 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.6364939 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.8133939 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.27414 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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 February 20, 2024 23:55