2-methyl-1,2-bis(pyridin-3-yl)propan-1-one

• ChemBase编号: 884
• 分子式: C14H14N2O
• 平均质量: 226.27376
• 单一同位素质量: 226.11061308
• SMILES: O=C(C(c1cccnc1)(C)C)c1cccnc1
• Canonical SMILES: O=C(C(c1cccnc1)(C)C)c1cccnc1
• InChI: InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3
• InChIKey: FJLBFSROUSIWMA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-methyl-1,2-bis(pyridin-3-yl)propan-1-one
• IUPAC传统名: metyrapone
• 商标名: Metapirone; Metapyron; Metapyrone; Metopiron; Metopyrone; Metopirone
• 别名: 2-甲基-1,2-二-3-吡啶基-1-丙酮; 美替拉酮; 2-甲基-1,2-二-3-吡啶基-1-丙酮; 2-Methyl-1,2-di-3-pyridyl-1-propanone; Metyrapone; Su-4885; Metyrapone; 2-Methyl-1,2-di-3-pyridyl-1-propanone; Methapyrapone; Mepyrapone; Methbipyranone; Methopirapone; Methopyrapone; Methopyrinine; Methopyrone; Metyrapon; Metroprione; Metyrapone; 2-Methyl-1,2-di-3-pyridyl-1-propanone

登记号

• CAS号: 54-36-4
• EC号: 200-206-2
• MDL号: MFCD00006397
• Beilstein号: 163023
• PubChem SID: 46504862; 160964347; 24888424
• PubChem CID: 4174
• CHEBI ID: 44241
• ATC码: V04CD01
• CHEMBL: 934
• Chemspider ID: 4030
• DrugBank ID: DB01011
• KEGG ID: D00410
• 美国药典/FDA物质标识码: ZS9KD92H6V
• 维基百科标题: Metyrapone

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.9471339
• LogD (pH = 7.4): 2.0277522
• Log P: 2.028889
• 摩尔折射率: 65.9444 cm^3
• 极化性: 25.544344 Å^3
• 极化表面积: 42.85 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -2.72
• 溶解度: 4.27e-01 g/l

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL; H2O: <2 mg/mL; Sparingly soluble
• 外观: solid
• 熔点: 52-55 °C(lit.)
• 闪点: >110 °C; >230 °F
• 疏水性(logP): 1.8

安全信息

• RTECS编号: UC3050000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: room temp

药理学性质

• 给药途径: Oral
• 半衰期: 1.9 ±0.7 hours.
• 妊娠期药物分类: C US

产品相关信息

• 纯度: ≥98% (HPLC); 95+%; 96%
• Empirical Formula (Hill Notation): C14H14N2O

详细说明

DrugBank - DB01011

• Drug Groups: approved
• Description: An inhibitor of the enzyme steroid 11-beta-monooxygenase. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of cushing syndrome. [PubChem]
• Indication: Used as a diagnostic drug for testing hypothalamic-pituitary ACTH function. Occasionally used in Cushing's syndrome.
• Pharmacology: Metopirone is an inhibitor of endogenous adrenal corticosteroid synthesis.
• Toxicity: Oral LD₅₀ in rats is 521 mg/kg. One case has been recorded in which a 6-year-old girl died after two doses of Metopirone, 2 g. Symptoms of overdose include cardiac arrhythmias, hypotension, dehydration, anxiety, confusion, weakness, impairment of consciousness, nausea, vomiting, epigastric pain, and diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. The major biotransformation is reduction of the ketone to metyrapol, an active alcohol metabolite. Metyrapone and metyrapol are both conjugated with glucuronide.
• Absorption: Absorbed rapidly and well when administered orally. Peak plasma concentrations are usually reached 1 hour after administration.
• Half Life: 1.9 ±0.7 hours.
• Elimination: After administration of 4.5 g metyrapone (750 mg every 4 hours), an average of 5.3% of the dose was excreted in the urine in the form of metyrapone (9.2% free and 90.8% as glucuronide) and 38.5% in the form of metyrapol (8.1% free and 91.9% as glucuronide) within 72 hours after the first dose was given.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M2696

Biochem/physiol Actions
Metyrapone is a glucocorticoid synthesis inhibitor; a standard in assessing adrenal gland function especially in response to stress, as well as pituitary gland function. In addition to acting as a glucocorticoid synthesis inhibitor, Metyrapone also inhibits cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activity and impairs learning and memory. Data shows results in activation of the sleep EEG and a robust decrease in quantitative delta sleep.

Sigma Aldrich - 856525

包装
1 g in glass bottle
250 mg in glass bottle