Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H10N2OS |
| Molecular Weight | 170.232 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1=CC(=O)NC(=S)N1
InChI
InChIKey=KNAHARQHSZJURB-UHFFFAOYSA-N
InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
| Molecular Formula | C7H10N2OS |
| Molecular Weight | 170.232 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Propylthiouracil is thyroid peroxidase inhibitor used to treat hyperthyroidism, which includes hyperthyroidism due to Graves' disease and toxic multinodular goiter. Propylthiouracil is used to ameliorate symptoms of hyperthyroidism in preparation for thyroidectomy or radioactive iodine therapy in patients who are intolerant of methimazole.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1839 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26509551 |
3.38 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PROPYLTHIOURACIL Approved UsePropylthiouracil is indicated: in patients with Graves' disease with hyperthyroidism or toxic multinodular goiter who are intolerant of methimazole and for whom surgery or radioactive iodine therapy is not an appropriate treatment option. to ameliorate symptoms of hyperthyroidism in preparation for thyroidectomy or radioactive iodine therapy in patients who are intolerant of methimazole. Launch Date1947 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479714/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.62 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30522550 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1385 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479714/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.19 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30522550 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
77 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479714/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.22 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30522550 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30522550 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROPYLTHIOURACIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Bitter taste of saccharin and acesulfame-K. | 2002-01 |
|
| Neonatal thyroid enlargement associated with propylthiouracil therapy of Graves' disease during pregnancy: a problem revisited. | 2001-12 |
|
| Adverse effects of prenatal methimazole exposure. | 2001-11 |
|
| Treatment of acrodermatitis continua of Hallopeau with oral propylthiouracil and methotrexate. | 2001-11 |
|
| Altered cross-bridge characteristics following haemodynamic overload in rabbit hearts expressing V3 myosin. | 2001-10-15 |
|
| Thyroidal regulation of different isoforms of NaKATPase in glial cells of developing rat brain. | 2001-10-05 |
|
| Relationship of papillae number to bitter intensity of quinine and PROP within and between individuals. | 2001-10 |
|
| Thyroid hormone-induced oxidative damage on lipids, glutathione and DNA in the mouse heart. | 2001-10 |
|
| Binary taste mixture interactions in prop non-tasters, medium-tasters and super-tasters. | 2001-10 |
|
| Differential regulation of SR calcium transporters by thyroid hormone in rat atria and ventricles. | 2001-10 |
|
| Development and validation of a high-performance liquid chromatographic method for the analysis of propylthiouracil in pharmaceuticals. | 2001-09 |
|
| Ca(2+)/nicotinamide adenine dinucleotide phosphate-dependent H(2)O(2) generation is inhibited by iodide in human thyroids. | 2001-09 |
|
| Is the infertility in hypothyroidism mainly due to ovarian or pituitary functional changes? | 2001-09 |
|
| Plasma total homocysteine in hyper- and hypothyroid patients before and during 12 months of treatment. | 2001-09 |
|
| Thyroid status and leptin in Basedow-Graves and multinodular goiter patients. | 2001-08-24 |
|
| Myasthenia gravis in conjunction with Graves' disease: a diagnostic challenge. | 2001-08-11 |
|
| Interplay of pregnancy, lactation, and hyperthyroidism leading to severe osteoporosis in a young woman. | 2001-08-11 |
|
| The human type 2 iodothyronine deiodinase is a selenoprotein highly expressed in a mesothelioma cell line. | 2001-08-10 |
|
| Hypothyroidism and nutritional status alter 3,5,3'-triiodothyronine (T3) receptors in isolated liver nuclei of Anabas testudineus (Bloch). | 2001-08 |
|
| 46, XY pure gonadal dysgenesis: a case with Graves' disease and exceptionally tall stature. | 2001-08 |
|
| Liver necrosis induced by thyroid hormone administration in rats fed ethanol. | 2001-08 |
|
| Increased intensity perception of aversive taste following right anteromedial temporal lobe removal in humans. | 2001-08 |
|
| Modulation of rat liver mitochondrial antioxidant defence system by thyroid hormone. | 2001-07-27 |
|
| Preparation and properties of a selenium-containing catalytic antibody as type I deiodinase mimic. | 2001-07-27 |
|
| Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms. | 2001-07 |
|
| Changes in autoimmune thyroid disease following allogeneic bone marrow transplantation. | 2001-07 |
|
| Development of brief methods to classify individuals by PROP taster status. | 2001-07 |
|
| Regulation of TRH and TRH-related peptides in rat brain by thyroid and steroid hormones. | 2001-07 |
|
| Effects of oxidative stress on the erythrocyte Na+,K+ ATPase activity in female hyperthyroid patients. | 2001-06-22 |
|
| [Acute alcoholic hepatitis: treatments]. | 2001-06-09 |
|
| Effect of propylthiouracil on adenosine deaminase activity and thyroid function in patients with psoriasis. | 2001-06 |
|
| Genetic taste responses to 6-n-propylthiouracil among adults: a screening tool for epidemiological studies. | 2001-06 |
|
| A selenium-containing catalytic antibody with Type I deiodinase activity. | 2001-05-25 |
|
| Myeloperoxidase-antineutrophil cytoplasmic antibody-associated sensorineural hearing loss. | 2001-05 |
|
| Short-term effects of thyroid hormones on lipogenic enzymes and 14C-acetate incorporation into various lipid classes: in vivo and in vitro studies. | 2001-05 |
|
| Fetal thyrotoxicosis after maternal thyroidectomy. | 2001-05 |
|
| Involvement of L-triiodothyronine in acetylcholine metabolism in adult rat cerebrocortical synaptosomes. | 2001-05 |
|
| [Pulmonary hypertension associated with refractory hyperthyroidism: a case report]. | 2001-05 |
|
| Frequency of appearance of myeloperoxidase-antineutrophil cytoplasmic antibody (MPO-ANCA) in Graves' disease patients treated with propylthiouracil and the relationship between MPO-ANCA and clinical manifestations. | 2001-05 |
|
| Method for the analysis of thyreostats in meat tissue using gas chromatography with nitrogen phosphorus detection and tandem mass spectrometric confirmation. | 2001-05 |
|
| [Pregnancy (conception) in hyper- or hypothyroidism]. | 2001-04-14 |
|
| Thiouracil antithyroid drugs as a new class of neuronal nitric oxide synthase inhibitors. | 2001-04-06 |
|
| Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy. | 2001-04 |
|
| Induction of autoimmune hypothyroidism and subsequent hyperthyroidism by TSH receptor antibodies following subacute thyroiditis: a case report. | 2001-04 |
|
| Short-term hyperthyroidism followed by transient pituitary hypothyroidism in a very low birth weight infant born to a mother with uncontrolled Graves' disease. | 2001-04 |
|
| Arrhythmogenesis in isolated rat hearts with enhanced alpha-adrenoceptor-mediated responsiveness. | 2001-02 |
|
| Drug-induced congenital defects: strategies to reduce the incidence. | 2001 |
|
| Membrane-Bound and cytosolic forms of heterotrimeric G proteins in young and adult rat myocardium: influence of neonatal hypo- and hyperthyroidism. | 2001 |
|
| 11Beta-hydroxysteroid dehydrogenase bioactivity is increased in the colon but not kidneys of rats given supplementary thyroxine. | 2001 |
|
| Liver disease caused by propylthiouracil. | 1975-02 |
Patents
Sample Use Guides
Propylthiouracil is administered orally. The total daily dosage is usually given in 3 equal doses at approximately 8 hour intervals. The initial dose in adults is 300 mg daily. In patients with severe hyperthyroidism, very large goiters, or both, the initial dose may be increased to 400 mg daily; an occasional patient will require 600 to 900 mg daily initially. The usual maintenance dose is 100 to 150 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26509551
Thyroid peroxidase activity was measured by monitoring the formation of resorufin from the oxidation of Amplex Red.Assay mixtures (100 uL) contained 50 mM sodium phosphate buffer, pH 7.4, 150 mM NaCl, 2 uM H2O2, 30 uM Amplex Red, 1 mM diethylenetriaminepentaacetic acid, and 2% DMSO. The reactions were initiated by the addition of TPO. Reaction mixtures to determine the background reaction rate consisted of all assay components and 4 uL of 500 unit/mL bovine catalase in 50 mM potassium phosphate buffer, pH 7.0. The background rate was subtracted from each reaction progress curve. IC50 for propylthiouracil was 3.38 uM.
| Substance Class |
Chemical
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| Record UNII |
721M9407IY
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Validated (UNII)
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| Classification Tree | Code System | Code | ||
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IARC | Propylthiouracil | ||
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WHO-ATC |
H03BA02
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NDF-RT |
N0000175917
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EPA PESTICIDE CODE |
57810
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NDF-RT |
N0000175918
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WHO-ESSENTIAL MEDICINES LIST |
18.8
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WHO-VATC |
QH03BA02
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LIVERTOX |
NBK547973
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NCI_THESAURUS |
C885
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8794
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51-52-5
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DB00550
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C781
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1578000
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4184
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721M9407IY
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8502
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Propylthiouracil
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CHEMBL1518
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SUB10123MIG
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200-103-2
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3390
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D011441
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m9250
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100000081364
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6650
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PROPYLTHIOURACIL
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PRIMARY | Description: Colourless or pale cream-coloured crystals or a white or cream-coloured, crystalline powder; odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Antithyroid substance. Storage: Propylthiouracil should be kept in a well-closed container, protected from light. Additional information: Propylthiouracil has a bitter taste. Definition: Propylthiouracil contains not less than 98.0% and not more than 100.5% of C7H10N2OS, calculated with reference tothe dried substance. | ||
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6498
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DTXSID5021209
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721M9407IY
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657298
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70461
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2308
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PROPYLTHIOURACIL
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC |
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