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Propylthiouracil

CAS# 51-52-5

Propylthiouracil

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Chemical structure

Propylthiouracil

3D structure

Chemical Properties of Propylthiouracil

Cas No. 51-52-5 SDF Download SDF
PubChem ID 657298 Appearance Powder
Formula C7H10N2OS M.Wt 170.23
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 6-n-Propylthiouracil; 6-Propyl-2-thiouracil; PTU
Solubility DMSO : ≥ 100 mg/mL (587.44 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 6-propyl-2-sulfanylidene-1H-pyrimidin-4-one
SMILES CCCC1=CC(=O)NC(=S)N1
Standard InChIKey KNAHARQHSZJURB-UHFFFAOYSA-N
Standard 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)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Propylthiouracil

DescriptionPropylthiouracil(6-Propyl-2-thiouracil) is a thyroperoxidase and 5'-deiodinase inhibitor. Target: Thyroperoxidase (TPO) Propylthiouracil (PTU) is a thiouracil-derived drug used to treat hyperthyroidism (including Graves' disease) by decreasing the amount of thyroid hormone produced by the thyroid gland [1]. The antithyroid drug 6-propylthiouracil (PTU) was shown to have an unexpectedly prolonged inhibitory effect on iodination in the thyroid glands of rats. Eighteen hours after injection of a relatively small dose, iodination in the thyroid remained inhibited by more than 90% [2]. PTU inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I-) to iodine (I0), facilitating iodine's addition to tyrosine residues on the hormone precursor thyroglobulin. This is one of the essential steps in the formation of thyroxine (T4). PTU does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells' basolateral membranes. Inhibition of this step requires competitive inhibitors, such as perchlorate and thiocyanate. From Wikipedia.

References:
[1]. Nakamura, H., et al., Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease. J Clin Endocrinol Metab, 2007. 92(6): p. 2157-62. [2]. Taurog, A. and M.L. Dorris, A reexamination of the proposed inactivation of thyroid peroxidase in the rat thyroid by propylthiouracil. Endocrinology, 1989. 124(6): p. 3038-42.

Propylthiouracil Dilution Calculator

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Propylthiouracil Molarity Calculator

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Preparing Stock Solutions of Propylthiouracil

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.8744 mL 29.372 mL 58.7441 mL 117.4881 mL 146.8601 mL
5 mM 1.1749 mL 5.8744 mL 11.7488 mL 23.4976 mL 29.372 mL
10 mM 0.5874 mL 2.9372 mL 5.8744 mL 11.7488 mL 14.686 mL
50 mM 0.1175 mL 0.5874 mL 1.1749 mL 2.3498 mL 2.9372 mL
100 mM 0.0587 mL 0.2937 mL 0.5874 mL 1.1749 mL 1.4686 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Propylthiouracil

[Pyoderma gangrenosum associated with anti-proteinase 3 antineutrophil cytoplasmic antibodies (PR3-ANCA) induced by propylthiouracil].[Pubmed:28291538]

Ann Dermatol Venereol. 2017 May;144(5):368-373.

BACKGROUND: Synthetic antithyroid drugs are often used in the treatment of hyperthyroidism, regardless of aetiology. They may cause various side effects, including the development of anti-neutrophil cytoplasmic antibodies (ANCA), ANCA-associated vasculitis, and neutrophilic dermatoses. Propylthiouracil (PTU) is the antithyroid drug most frequently implicated in ANCA-associated diseases specifically involving anti-myeloperoxidase ANCA (MPO-ANCA). To our knowledge, there are no clinical reports describing the association of pyoderma gangrenosum (PG) and anti-proteinase3-ANCA (PR3-ANCA) induced by PTU, with ANCA levels decreasing after antithyroid drug withdrawal. PATIENTS AND METHODS: A 68-year-old woman was treated with Propylthiouracil (PTU) for toxic multinodular goitre. She presented necrotic ulceration of the lower abdomen. The patient's history, physical examination, and bacteriological and histological samples led to a diagnosis of pyoderma gangrenosum. This pyoderma involved ANCA with antigenic specificity for proteinase 3. Withdrawal of PTU and a short course of corticosteroids and cyclosporine resulted in rapid and complete resolution of the pyoderma gangrenosum as well as a decrease in ANCA. No relapse was observed one year after cessation of treatment. DISCUSSION: We report a case of PG associated with PR3-ANCA induced by PTU, without any demonstrable vasculitis.

Relationship of recovered hepatitis B infection with appearance of toxic propylthiouracil hepatitis.[Pubmed:28165437]

Med Glas (Zenica). 2017 Feb 1;14(1):79-84.

Aim To investigate the relationship between recovered hepatitis B infection with appearance of toxic Propylthiouracil (PTU) hepatitis and point out the growing importance of the use of drugs in the development of hepatitis. Methods A case of a 45-year-old female patient with suspicion of acute viral hepatitis who had polypragmasy of drugs in the last ten years, due to the polymorphism of symptoms/illnesses (diabetes mellitus, depression, hypertension, hypothyroidism) was presented. Results A female patient had hyperthyroidism after resolved viral hepatitis B with HBsAg seroconversion (HBsAg negative, antiHBs positive). PTU had the greatest potential for hepatotoxicity of all administered drugs. After corticosteroid therapy there was a significant improvement in liver function tests. In the course of the disease there was no change of hepatitis markers and exacerbations of hepatitis B. Conclusion Clinical practice should comprehensively monitor the effects of the intricate and tight connection between drugs, liver and endocrine system in order to better resolve all manifestations, complications and worsening of one or another organic system.

Propylthiouracil-induced liver failure and artificial liver support systems: a case report and review of the literature.[Pubmed:28138249]

Ther Clin Risk Manag. 2017 Jan 11;13:65-68.

BACKGROUND: Antithyroid drugs carry a potential risk of hepatotoxicity. Propylthiouracil (PTU) is commonly prescribed for patients with hyperthyroidism. PTU, however, can induce liver injury, ranging from mild asymptomatic elevation of aminotransferases to acute liver failure (ALF). CASE PRESENTATION: This case reports on a 16-year-old Chinese girl with hyperthyroidism, who was admitted to our hospital for jaundice, nausea, and fatigue associated with severe hyperbilirubinemia and coagulopathy. She had been prescribed PTU 5 months earlier. There was no history of hypersensitivity to drugs, viral liver diseases, blood transfusion, or surgery. On the basis of her symptoms and the clinical data, she was diagnosed with PTU-induced ALF. Due to the limited number of available donor organs for liver transplantation, she was started on treatment with artificial liver support system (ALSS). After four sessions of ALSS, her clinical signs and symptoms were found to be markedly improved, and she was discharged 25 days after admission. Four months later, her liver function normalized. CONCLUSION: Although PTU-induced liver failure is rare in clinical practice, liver function should be appropriately monitored during treatment with PTU. PTU-induced ALF in this patient was successfully managed with an ALSS, suggesting that the latter may be an alternative to liver transplantation.

Genetic specificity to 6-n-propylthiouracil and its association to dental caries: A Comparative study.[Pubmed:28139488]

J Indian Soc Pedod Prev Dent. 2017 Jan-Mar;35(1):83-85.

INTRODUCTION: Dental caries is one of the most prevalent infectious diseases to affl ict humanity. Although caries has multifactorial etiology, inherited genetic behavior and taste threshold may play an important role on caries. MATERIAL AND METHOD: Thirty mothers and thirty children in the age group of 6-14 years of both sexes who have stable mental condition and ASA physical status were selected for the study & 6-n-Propylthiouracil testing is done. RESULTS: It is observed that nontaster siblings have higher caries prevalence than medium tasters and supertasters. DISCUSSION: Genetic sensitivity to taste is an inherited trait in children from their parents, inheritance from mother being more pronounced. Hence, this study is intended. CONCLUSION: Dental caries is multi-factorial. No significant correlation between susceptibility of mother and child to genetic sensitivity exists, and genetic sensitivity is not the only criteria for severity.

Description

Propylthiouracil(6-Propyl-2-thiouracil) is a thyroperoxidase and 5'-deiodinase inhibitor.

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