Propylthiouracil

Base Information

• Chemical Name: Propylthiouracil
• CAS No.: 51-52-5
• Deprecated CAS: 500-50-5
• Molecular Formula: C7H10N2OS
• Molecular Weight: 170.235
• Hs Code.: 29335995
• European Community (EC) Number: 200-103-2
• NSC Number: 757302,70461,6498
• UNII: 721M9407IY
• DSSTox Substance ID: DTXSID5021209
• Nikkaji Number: J1.363C
• Wikipedia: Propylthiouracil
• Wikidata: Q377342
• NCI Thesaurus Code: C781
• RXCUI: 8794
• Pharos Ligand ID: TMC3KAZX3T4H
• Metabolomics Workbench ID: 42886
• ChEMBL ID: CHEMBL1518
• Mol file: 51-52-5.mol

Synonyms:6 Propyl 2 Thiouracil;6-Propyl-2-Thiouracil;Propylthiouracil

Chemical Property of Propylthiouracil

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 218-220 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 355.2 °C at 760 mmHg
• PKA: pKa 7.8; 8.3 (Uncertain)
• Flash Point: 168.6 °C
• PSA: 80.74000
• Density: 1.24 g/cm³
• LogP: 1.38500
• Storage Temp.: Refrigerator
• Solubility.: 1.1g/l
• Water Solubility.: 1.1 g/L
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 170.05138412
• Heavy Atom Count: 11
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

Propylthiouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-40
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithyroid Agents
• Canonical SMILES: CCCC1=CC(=O)NC(=S)N1
• Recent ClinicalTrials: Networked Drug REpurposing for Mechanism-based neuroPrOtection in Acute Ischaemic STROKE
• Recent EU Clinical Trials: Prospective Randomized Clinical Trial of Total Thyroidectomy (Tx) versus Thionamides (Anti-Thyroid Drugs) in Patients with Moderate-to-Severe Graves’ Ophthalmopathy - a 1-year Follow-up
• Description: Propylthiouracil (PTU) is a thioamide antithyroid agent. It inhibits thyroid peroxidase activity in rat and monkey thyroid microsomes (IC50s = 0.081 and 4.1 μM, respectively). PTU (30 mg/kg) increases thyroid weight and serum thyroid stimulating hormone levels and decreases serum 3,5,3''-triiodothyronine and thyroxine levels in rats. Sensitivity to the bitter taste of PTU is genetically mediated and is associated with increased sensitivity to other sweet and bitter compounds. Formulations containing propylthiouracil have been used in the treatment of Graves'' disease and hyperthyroidism.
• Uses: Antihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen antibacterial Antihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen.
• Clinical Use: Propylthiouracil is useful in the treatment of hyperthyroidism.There is a delay in appearance of its effects because propylthiouracildoes not interfere with the activity of thyroid hormonesalready formed and stored in the thyroid gland. Thislag period may vary from several days to weeks, dependingon the condition of the patient. The need for three equallyspaced doses during a 24-hour period is often stressed, butevidence now indicates that a single daily dose is as effectiveas multiple daily doses in the treatment of most hyperthyroidpatients.
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Propylthiouracil

There total 7 articles about Propylthiouracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

ethyl butyroyl acetate (3249-68-1) + thiourea (17356-08-0) → propylthiouracil (51-52-5)

Guidance literature:

Reflux;

DOI:10.3390/molecules25153379

Reference yield: 78.0%

thiourea (17356-08-0) + methyl 3-oxohexanoate (30414-54-1) → propylthiouracil (51-52-5)

Guidance literature:

With potassium carbonate; In water; at 70 - 105 ℃; for 3h;

Reference yield:

→ propylthiouracil (51-52-5)

Guidance literature:

6-Propyl-2-thioxo-2,3-dihydro-1H-<2-¹⁴C>pyrimidin-4-on;

upstream raw materials:

ethyl butyroyl acetate

thiourea

methyl 3-oxohexanoate

Downstream raw materials:

2-benzylsulfanyl-6-propyl-3H-pyrimidin-4-one

2-(methylthio)-6-propylpyrimidin-4(3H)-one

6-propyl(1H,3H)pyrimidine-2,4-dione

6-n-propyl-2-methylthio-4-pyrimidone

Refernces

• 1、 Abdel-Mohsen,Conrad,Harms,Nohr,Beifuss. "Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers". . p. 17427 - 17441. Retrieved 2017/03/31.
• 2、 Nikpour, Mohsen,Mousavian, Mina,Davoodnejad, Mahdieh,Alimardani, Maliheh,Sadeghian, Hamid. "Synthesis of new series of pyrimido[4,5-b][1,4] benzothiazines as 15-lipoxygenase inhibitors and study of their inhibitory mechanism". . p. 5036 - 5043. Retrieved 2013/09/23.