6-Propyl-2-thiouracil - Moligand™, ≥98% , CAS No.51-52-5

CAS: 51-52-5 Cat. No.: P106338 Molecular Weight: 170.23 Beilstein Registry Number: 130039 EC Number: 200-103-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

6-PTU | BSPBio_000387 | PROPYLTHIOURACIL [IARC] | PROPYLTHIOURACIL [EP MONOGRAPH] | Propylthiouracil; 2,3-dihydro-6-propyl-2-thioxopyrimidin-4(1H)-one | Propylthiouracilum [INN-Latin] | 6-propyl-2-thioxo-1H-pyrimidin-4-one | AI3-25477 | Propylthiorit | Pr

Storage

Room temperature

Shipped In

Normal

Overview

6-PTU is a thiolated uracil derivativewhich has been shown to acts as an antihyperthyroid agent. 6-Propyl-2-thiouracil is known to inhibit the deiodination of thyroxine to triiodothyronine via deiodinase, iodothyronine, type I (DIO1).
It is a thyreostatic (thyroid hormone) agent that may be used as a reference material in thyreostatic drug separation and detection technologies such as capillary electrophoresis, HPLC, or gas chromatography.

Specifications

Synonyms

6-PTU | BSPBio_000387 | PROPYLTHIOURACIL [IARC] | PROPYLTHIOURACIL [EP MONOGRAPH] | Propylthiouracil; 2, 3-dihydro-6-propyl-2-thioxopyrimidin-4(1H)-one | Propylthiouracilum [INN-Latin] | 6-propyl-2-thioxo-1H-pyrimidin-4-one | AI3-25477 | Propylthiorit | Pr

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Non-competitive type I iodothyronine deiodinase inhibitor (IC 50 = 0.2 μM). Thyroperoxidase inhibitor. Inhibits 5'-deiodinase peripherally. Reduces the production of thyroxine in vivo. Centrally active.

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488191003
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488191003
• Canonical Smiles: CCCC1=CC(=O)NC(=S)N1
• IUPAC Name: 6-propyl-2-sulfanylidene-1H-pyrimidin-4-one
• 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)
• Isomeric SMILES: CCCC1=CC(=O)NC(=S)N1
• WGK Germany: 3
• RTECS: YR1400000
• Molecular Weight: 170.23
• Beilstein: 130039
• Reaxy-Rn: 130039
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=130039&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidones
• Alternative Parents: Pyrimidinethiones 2-Thiopyrimidines Hydropyrimidines Vinylogous amides Heteroaromatic compounds Thioureas Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-thiopyrimidine - Pyrimidinethione - Thiopyrimidine - Pyrimidone - Hydropyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Thiourea - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• 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.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TAS2R38 Tchem Taste receptor type 2 member 38 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TPO Tclin Thyroid peroxidase (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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HMGCR Tclin HMG-CoA reductase (2475 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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INSR Tclin Insulin receptor (5558 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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TPO Tclin Thyroid peroxidase (64 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Rattus norvegicus (775804 Activities)

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MDCK (10148 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Plasma (328 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Glra2 Glycine receptor (1745 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in 10% ammonia, water (1.1 mg/ml) at 20 °C, DMSO, methanol, 1 N NaOH (50 mg/ml), aclcohol (16 mg/ml), and water (10 mg/ml,boiling). Insoluble in ether, chloroform, and benzene.
• Sensitivity: light sensitive
• Flash Point(°F): 300 °C
• Flash Point(°C): 300°C
• Melt Point(°C): 218-221°C
• Molecular Weight: 170.230 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 170.051 Da
• Monoisotopic Mass: 170.051 Da
• Topological Polar Surface Area: 73.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 222.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yongjie Zhang, Luyao Feng, Jingyan Luan, Guomei Zhang, Ning Sheng, Jinglin Shen.  (2023)  A cooperative effect of copper-induction and AIE leading to bright luminescence of gold nanoclusters.  Inorganic Chemistry Frontiers,  11  (1): (237-245).  [PMID:] [10.1039/D3QI01974H]

2. Yanmin Shen, Yu Bi, Peixia Zhao, Xiaolong Yang, Zheng Zhang, Dan Dang, Han Wang, Wenju Liu.  (2023)  Equilibrium solubility of 6-propyl-2-thiouracil in nine pure solvents: Determination, correlation, Hansen solubility parameter and thermodynamic properties.  JOURNAL OF THE INDIAN CHEMICAL SOCIETY,      [PMID:] [10.1016/j.jics.2023.100934]

3. Wenju Liu, Yanmin Shen, Fankun Zeng, Shuanghui Lu, Jun Li, Jinjin Yang, Kewen Zhang.  (2021)  Solubility Measurement and Model Correlating of 6-Propyl-2-Thiouracil in Four Binary Solvents at 278.15–323.15 K.  JOURNAL OF CHEMICAL AND ENGINEERING DATA,      [PMID:] [10.1021/acs.jced.1c00071]

4. Min Li, Qingfeng He, Li Yao, Xiaofeng Wang, Zhijia Tang, Xiao Zhu, Hai-Shu Lin, Xiaoqiang Xiang.  (2021)  Simultaneous Quantification of Propylthiouracil and Its N-β-d Glucuronide by HPLC-MS/MS: Application to a Metabolic Study.  Pharmaceuticals,  14  (11): (1194).  [PMID:34832976] [10.3390/ph14111194]

5. Yuntian Xiao, Wenchao Yang, Ling Zhou, Hongxun Hao, Ying Bao, Qiuxiang Yin, Chuang Xie.  (2021)  Growth mechanism of the spherulitic propylthiouracil–kaempferol cocrystal: new perspectives into surface nucleation.  CRYSTENGCOMM,  23  (12): (2367-2375).  [PMID:] [10.1039/D1CE00022E]