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51-52-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:432 http://www.chembase.cn/molecule-432.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
51-52-5
EC Number
200-103-2
MDL Number
MFCD00006041
Beilstein Number
130039
PubChem SID
24898446
46505181
160963895
24870375
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.089443  H Acceptors
H Donor LogD (pH = 5.5) 1.2026387 
LogD (pH = 7.4) 1.1239698  Log P 1.2037424 
Molar Refractivity 48.9043 cm3 Polarizability 18.43689 Å3
Polar Surface Area 41.13 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.53  LOG S -2.56 
Solubility (Water) 4.66e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1200 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
218-220 °C(lit.) expand Show data source
219°C expand Show data source
219-221 °C expand Show data source
219-221°C expand Show data source
Flash Point
300 °C expand Show data source
572 °F expand Show data source
Partition Coefficient
0.76 expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
YR1400000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-40 expand Show data source
R:22-45 expand Show data source
Safety Statements
36/37 expand Show data source
S:28-36/37/39-45-53 expand Show data source
S:36/37/39-53 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H351 expand Show data source
GHS Precautionary statements
P281 expand Show data source
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 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
80%-95% expand Show data source
Half Life
2 hours expand Show data source
Pregnancy Category
D expand Show data source
Purity
95+% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Description
enzyme inhibitor expand Show data source
Empirical Formula (Hill Notation)
C7H10N2OS expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02102748 external link
Crystalline
SUSPECTED CARCINOGEN!
MP Biomedicals - 05206639 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00550 external link
Item Information
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 external link
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 external link
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 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - P838310 external link
Antihyperthyroid. Has been used to promote fattening. This substance is reasonably anticipated to be a human carcinogen.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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