6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

• ChemBase ID: 432
• Molecular Formular: C7H10N2OS
• Molecular Mass: 170.2321
• Monoisotopic Mass: 170.05138395
• SMILES: S=c1[nH]c(CCC)cc(=O)[nH]1
• Canonical SMILES: CCCc1cc(=O)[nH]c(=S)[nH]1
• 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)
• InChIKey: KNAHARQHSZJURB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
• IUPAC Traditional name: propylthiouracil
• Brand Name: Thyreostat II
• Synonyms: Propilthiouracil; Propyl-Thyracil; Propyl-Thiorit; Propyl-Thiorist; Propythiouracil; PTU; Procasil; Propacil; Thiuragyl; Protiural; Prothyran; Prothycil; Prothiurone; Prothiucil; Propylthiorit; Propycil; Propylthiouracil; 6-n-Propylthiouracil; 6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one; 2,3-Dihydro-6-propyl-2-thioxo-4(1H)pyrimidinone; 6-Propyl-2-thiouracil; 2-Mercapto-4-hydroxy-6-n-propylpyrimidine; 2-Mercapto-6-propylpyrimidin-4-ol; NSC 6498; NSC 70461; 4-Hydroxy-2-mercapto-6-propylpyrimidine; 6-n-PROPYL-2-THIOURACIL; 6-n-PROPYL-2-MERCAPTO-4-HYDROXYPYRIMIDINE; 6-Propyl-2-thiouracil; 4-羟基-2-巯基-6-丙基嘧啶; 6-丙基-2-硫尿嘧啶

Database IDs

• CAS Number: 51-52-5
• EC Number: 200-103-2
• MDL Number: MFCD00006041
• Beilstein Number: 130039
• PubChem SID: 24870375; 24898446; 46505181; 160963895
• PubChem CID: 657298
• CHEBI ID: 8502
• ATC CODE: H03BA02
• CHEMBL: 1518
• Chemspider ID: 571424
• DrugBank ID: DB00550
• KEGG ID: D00562
• Unique Ingredient Identifier: 721M9407IY
• Wikipedia Title: Propylthiouracil
• Medline Plus: a682465

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.089443
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.2026387
• LogD (pH = 7.4): 1.1239698
• Log P: 1.2037424
• Molar Refractivity: 48.9043 cm^3
• Polarizability: 18.43689 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.53
• LOG S: -2.56
• Solubility (Water): 4.66e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1200 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 218-220 °C(lit.); 219°C; 219-221 °C; 219-221°C
• Flash Point: 300 °C; 572 °F
• Partition Coefficient: 0.76
• Hydrophobicity(logP): 0.4

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: YR1400000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-40; R:22-45
• Safety Statements: 36/37; S:28-36/37/39-45-53; S:36/37/39-53
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 80%-95%
• Half Life: 2 hours
• Pregnancy Category: D

Product Information

• Purity: 95+%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Description: enzyme inhibitor
• Empirical Formula (Hill Notation): C7H10N2OS

DETAILS

MP Biomedicals - 02102748

Crystalline
SUSPECTED CARCINOGEN!

MP Biomedicals - 05206639

MP Biomedicals Rare Chemical collection

DrugBank - DB00550

• Drug Groups: approved
• Description: 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)
• Indication: Used to manage hyperthyroidism which is due to an overactive thyroid gland (Grave's disease).
• Pharmacology: 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.
• Toxicity: Oral, rat: LD₅₀ = 1250 mg/kg.
• Affected Organisms: Humans and other mammals
• Absorption: Well absorbed following oral administration.
• Half Life: 2 hours
• Protein Binding: 82%
• 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.
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1988

Research Area: Endocrinology ,
Biological Activity:
Propylthiouracil is a thyroperoxidase and 5’-deiodinase inhibitor. It is a thioamide drug used to treat hyperthyroidism (including Graves’ disease) by decreasing the amount of thyroid hormone produced by the thyroid gland. It 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. It also acts by inhibiting the enzyme 5’-deiodinase (tetraiodothyronine 5’ deiodinase), which converts T4 to the active form T3. [1]

Sigma Aldrich - P3755

包装
10, 25, 100 g in glass bottle
Application
6-Propyl-2-thiouracil 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.

Sigma Aldrich - 46698

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P838310

Antihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen.

REFERENCES

• http://en.wikipedia.org/wiki/Propylthiouracil
• Aboul-Enein, H.Y., et al.: Anal. Profiles Drug Subs., 6, 457 (1977)
• Cooper, D.S., et al.: N. Engl. J. Med., 311, 1353 (1977)