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

• ChemBase ID: 884
• Molecular Formular: C14H14N2O
• Molecular Mass: 226.27376
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-1,2-bis(pyridin-3-yl)propan-1-one
• IUPAC Traditional name: metyrapone
• Brand Name: Metapirone; Metapyron; Metapyrone; Metopiron; Metopyrone; Metopirone
• Synonyms: 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; 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

Database IDs

• CAS Number: 54-36-4
• EC Number: 200-206-2
• MDL Number: MFCD00006397
• Beilstein Number: 163023
• PubChem SID: 160964347; 46504862; 24888424
• PubChem CID: 4174
• CHEBI ID: 44241
• ATC CODE: V04CD01
• CHEMBL: 934
• Chemspider ID: 4030
• DrugBank ID: DB01011
• KEGG ID: D00410
• Unique Ingredient Identifier: ZS9KD92H6V
• Wikipedia Title: Metyrapone

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.9471339
• LogD (pH = 7.4): 2.0277522
• Log P: 2.028889
• Molar Refractivity: 65.9444 cm^3
• Polarizability: 25.544344 Å^3
• Polar Surface Area: 42.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -2.72
• Solubility (Water): 4.27e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: <2 mg/mL; Sparingly soluble
• Apperance: solid
• Melting Point: 52-55 °C(lit.)
• Flash Point: >110 °C; >230 °F
• Hydrophobicity(logP): 1.8

Safety Information

• RTECS: UC3050000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 1.9 ±0.7 hours.
• Pregnancy Category: C US

Product Information

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

DETAILS

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

Packaging
1 g in glass bottle
250 mg in glass bottle