1-methyl-2,3-dihydro-1H-imidazole-2-thione

• ChemBase编号: 643
• 分子式: C4H6N2S
• 平均质量: 114.16884
• 单一同位素质量: 114.0251692
• SMILES: S=c1n(cc[nH]1)C
• Canonical SMILES: Cn1cc[nH]c1=S
• InChI: InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
• InChIKey: PMRYVIKBURPHAH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-methyl-2,3-dihydro-1H-imidazole-2-thione
• IUPAC传统名: methimazole; 1-methyl-2,3-dihydro-1H-imidazole-2-thione
• 商标名: Basolan; Danantizol; Favistan; Frentirox; Merkastan; Metizol; Metotirin; Strumazol; Strumazole; Tapazole; Tapuzole; Thacapzol; Thycapsol; Thycapzol
• 别名: 1-甲基-2-咪唑硫醇; 2-巯基-1-甲基咪唑; 甲巯咪唑; 甲巯咪唑; 2-巯基-1-甲基咪唑; Thymidazole; Thymidazol; Thimazole; Thiamazole; Thiamazol; Metothyrine; Metothyrin; Methimazol; Methiamazole; Methamazole; Metazolo; Merkazolil; Mercazolyl; Mercazole; Mercasolyl; Mercaptazole; Methimazole; Methimazole; Thiamazole; 1-Methyl-1H-imidazole-2(3H)-thione; Basolan; 1-Methyl-1H-imidazole-2-thiol; 2-Mercapto-1-methyl-1H-imidazole; 1,3-Dihydro-1-methyl-2H-imidazole-2-thione; 2-Mercapto-1-methylimidazole; 1-Methylimidazole-2-thiol; 1-Methyl-2-imidazolethiol; Methimazole; 2-Mercapto-1-methylimidazole

登记号

• CAS号: 60-56-0
• EC号: 200-482-4
• MDL号: MFCD00179321
• Beilstein号: 108646
• PubChem SID: 24858194; 24882870; 160964106; 24897266; 46506536; 24870159
• PubChem CID: 1349907
• CHEBI ID: 50673
• ATC码: H03BB02
• CHEMBL: 1515
• Chemspider ID: 1131173
• DrugBank ID: DB00763
• KEGG ID: D00401
• 美国药典/FDA物质标识码: 554Z48XN5E
• 维基百科标题: Methimazole
• Medline Plus: a682464

理论计算性质

JChem

• Acid pKa: 10.411967
• 质子受体: 0
• 质子供体: 1
• LogD (pH = 5.5): 0.74566555
• LogD (pH = 7.4): 0.74527997
• Log P: 0.7456705
• 摩尔折射率: 33.2322 cm^3
• 极化性: 12.8416 Å^3
• 极化表面积: 15.27 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -1.0
• 溶解度: 1.13e+01 g/l

分子性质

理化性质

• 溶解度: 2.75 mg/mL (20°C); 275 g/L
• 熔点: 143-145 °C; 144-147 °C(lit.); 144-147°C; 146°C (294.8°F); 146-148
• 沸点: 280(dec.)°C
• 闪点: >100°C
• 疏水性(logP): -0.2

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 保存注意事项: Harmful/Irritant/Teratogenic/Stench/Store under Argon
• RTECS编号: NI8615000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-43-62; R:22
• 安全公开号: 26-27-36-45; S:36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H317-H361
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, 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: 93%
• 排泄: Renal
• 半衰期: 5-6 hours
• 代谢: Hepatic
• 蛋白结合率: None
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: D (US)
• 相关基因信息: human ... CYP1A2(1544)
• 生物活性机理: Thyroid hormone synthesis inhibitor

产品相关信息

• 纯度: ≥97.0% (S); ≥99%; 95+%; 98%
• 级别: analytical standard; purum; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Antithyroid; Used in treatment of hyperthyroidism
• Empirical Formula (Hill Notation): C4H6N2S

详细说明

MP Biomedicals - 02155390

(2-Mercapto-1-methylimidazole; 1-Methylimidazole-2-thiol) Purity: 98% Crystalline

DrugBank - DB00763

• Drug Groups: approved
• Description: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme. [PubChem]
• Indication: For the treatment of hyperthyroidism, goiter, Graves disease and psoriasis.
• Pharmacology: Used in the treatment of hyperthyroidism or an overactive thyroid gland, methimazole inhibits the synthesis of thyroid hormones and thus is effective in the treatment of hyperthyroidism. It may also be used to ameliorate hyperthyroidism in preparation for subtotal thyroidectomy or radioactive iodine therapy.
• Toxicity: Oral LD₅₀ in rats is 2250 mg/kg. Symptoms of overdose include nausea, vomiting, epigastric distress, headache, fever, joint pain, pruritus, and edema. Aplastic anemia (pancy-topenia) or agranulocytosis may be manifested in hours to days. Less frequent events are hepatitis, nephrotic syndrome, exfoliative dermatitis, neuropathies, and CNS stimulation or depression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Metabolized rapidly, requiring frequent administration.
• Absorption: Rapid with an oral bioavailability of 93%.
• Half Life: 5-6 hours
• Protein Binding: None or minimal
• Elimination: Methimazole is excreted in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1609

Research Area: Endocrinology
Biological Activity:
Methimazole(Tapazole, Northyx) is an antithyroid medicine. Methimazole is used to treat hyperthyroidism, a condition where the thyroid gland produces too much thyroid hormone. It is also used before thyroid surgery or radioactive iodine treatment. [1] Methimazole inhibits the addition of iodine to thyroglobulin by the enzyme thyroperoxidase, a necessary step in the synthesis of triiodothyronine(T3) and thyroxine(T4). It does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells’ basolateral membranes. Inhibition of this step requires competitive inhibitors such as perchlorate and thiocyanate. [1]

Sigma Aldrich - 301507

包装
5, 25 g in glass bottle

Sigma Aldrich - 46429

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - M8506

Application
Used to model hypothyroidism in experimental animals.
Biochem/physiol Actions
甲巯咪唑为硫脲抗甲状腺剂，可阻止碘有机化，从而抑制甲状腺素的合成。
包装
25, 100 g in glass bottle

参考文献

• http://en.wikipedia.org/wiki/Methimazole
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• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 617A, (ir)
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• Raper, E.S. et al., Acta Cryst. B, 1983, 39, 355, (cryst struct)
• Anjaneyulu, B. et al., J. Labelled Compd. Radiopharm., 1983, 20, 951, (synth)
• Merck Index, 10th edn., 1983, No. 5844
• Cooper, D.S. et al., Endocrinology (Baltimore), 1984, 114, 786, (pharmacol)
• Stefaniak, L. et al., Magn. Reson. Chem., 1986, 23, 166, (tautom)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 180, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 534
• Guziec, L.J. et al., J.O.C., 1994, 59, 4691, (synth, cmr)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCO500