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

• ChemBase编号: 432
• 分子式: C7H10N2OS
• 平均质量: 170.2321
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
• IUPAC传统名: propylthiouracil
• 商标名: Thyreostat II
• 别名: 4-羟基-2-巯基-6-丙基嘧啶; 6-丙基-2-硫尿嘧啶; 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

登记号

• CAS号: 51-52-5
• EC号: 200-103-2
• MDL号: MFCD00006041
• Beilstein号: 130039
• PubChem SID: 24898446; 46505181; 160963895; 24870375
• PubChem CID: 657298
• CHEBI ID: 8502
• ATC码: H03BA02
• CHEMBL: 1518
• Chemspider ID: 571424
• DrugBank ID: DB00550
• KEGG ID: D00562
• 美国药典/FDA物质标识码: 721M9407IY
• 维基百科标题: Propylthiouracil
• Medline Plus: a682465

理论计算性质

JChem

• Acid pKa: 8.089443
• 质子受体: 1
• 质子供体: 2
• LogD (pH = 5.5): 1.2026387
• LogD (pH = 7.4): 1.1239698
• Log P: 1.2037424
• 摩尔折射率: 48.9043 cm^3
• 极化性: 18.43689 Å^3
• 极化表面积: 41.13 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.53
• LOG S: -2.56
• 溶解度: 4.66e-01 g/l

分子性质

理化性质

• 溶解度: 1200 mg/L; DMSO; Methanol
• 外观: White Solid
• 熔点: 218-220 °C(lit.); 219°C; 219-221 °C; 219-221°C
• 闪点: 300 °C; 572 °F
• 分配系数: 0.76
• 疏水性(logP): 0.4

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: YR1400000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-40; R:22-45
• 安全公开号: 36/37; S:28-36/37/39-45-53; S:36/37/39-53
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H351
• GHS警示性声明: P281
• 个人保护装置: 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

药理学性质

• 给药途径: Oral
• 生物利用度: 80%-95%
• 半衰期: 2 hours
• 妊娠期药物分类: D

产品相关信息

• 纯度: 95+%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 简要说明: enzyme inhibitor
• Empirical Formula (Hill Notation): C7H10N2OS

详细说明

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

法律信息
VETRANAL 商标 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.

参考文献

• 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)