CAS 54-36-4|Methapyrapone|2-methyl-1,2-bis(pyridin-3-yl)propan-1-one|Methbipyranone|Methopyrapone|Methopyrone|Metroprione|Mepyrapone|Metopiron|Metapyron|Metyrapone|Metopirone|Metapirone|Methopirapon...

General Information

Structure

Molecular Formula

C₁₄H₁₄N₂O

Molecular Mass

226.27376

Exact Mass

226.11061308

Charge

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

Canonic Smiles

O=C(C(c1cccnc1)(C)C)c1cccnc1

Isomeric Smiles

O=C(C(c1cccnc1)(C)C)c1cccnc1

Calculated Properties

JChem

LogD (pH = 7.4)

2.03

LogD (pH = 5.5)

1.95

Log P

2.03

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.87

Polar Surface Area

42.85

Polarizability

23.95

Molar Refractivity

65.94

LOG S

-1.63

Data Source

Names and Identifiers

Synonyms

MethopyroneMethbipyranoneMethopyraponeMethopiraponeMethapyraponeMetyraponeMetroprioneMetyraponMepyraponeMethopyrinine2-Methyl-1,2-di-3-pyridyl-1-propanone美替拉酮Su-48852-甲基-1,2-二-3-吡啶基-1-丙酮Metyrapone2-Methyl-1,2-di-3-pyridyl-1-propanone2-甲基-1,2-二-3-吡啶基-1-丙酮Metyrapone2-Methyl-1,2-di-3-pyridyl-1-propanoneMetyraponeMETYRAPONEmetyrapone

Brand Name

MetapyroneMetopironMetapyronMetopyroneMetopironeMetapirone

IUPAC Traditional name

metyrapone

IUPAC name

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

International Nonproprietary Name (INN)

metyraponemetyraponummetirapona

Names and Identifiers

Registration numbers

Beilstein Number

163023

CAS Number

54-36-4

EC Number

200-206-2

PubChem SID

248884244650486216096434726697184

MDL Number

MFCD00006397

PubChem CID

4174

ATC CODE

V04CD01

Unique Ingredient Identifier

DrugBank ID

CHEMBL

KEGG ID

Chemspider ID

CHEBI ID

44241CHEBI:6911CHEBI:44238CHEBI:44241

Wikipedia Title

Metyrapone

Drug Central Database

1,791

MetaboLights Database

MTBLS2267MTBLS3750MTBLS1693

UniProt Database

D5JBW8P80701Q9FH76P80702

PDBeChem Database

MYT

BRENDA Ligand Database

172767

BindingDB Database

50028166

LINCS Database

LSM-3035

Patent number

US2008076828US2008057068US2008076829

Protein Data Bank

6ma67e7f1phg4zf81w0g

ACToR Database

37245-80-054-36-4

KEGG DRUG Database

D00410

EnzymePortal Database

SABIO-RK Database

SureChEMBL Database

Reaxys Registry

CompTox Database

BKMS React Database

Registration numbers

Properties

Pharmacology Properties

Half Life

1.9 ±0.7 hours.

Admin Routes

Oral

Pregnancy Category

C US

Product Information

Empirical Formula (Hill Notation)

C14H14N2O

Purity

96%

≥98% (HPLC)

95+%

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Metyrapone

Sigma Aldrich

856525

Packaging
1 g in glass bottle
250 mg in glass bottle

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.

ChEBI

CHEBI:44241

An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.

Molecule Details

References

PubChem Literature

No Data Available

Click here to submit data

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

MetapyroneMetopironMetapyronMetopyroneMetopironeMetapirone

IUPAC Traditional name

metyrapone

IUPAC name

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

International Nonproprietary Name (INN)

metyraponemetyraponummetirapona

Registration numbers

Beilstein Number

163023

CAS Number

54-36-4

EC Number

200-206-2

PubChem SID

248884244650486216096434726697184

MDL Number

MFCD00006397

PubChem CID

4174

ATC CODE

V04CD01

Unique Ingredient Identifier

DrugBank ID

CHEMBL

KEGG ID

Chemspider ID

CHEBI ID

44241CHEBI:6911CHEBI:44238CHEBI:44241

Wikipedia Title

Metyrapone

Drug Central Database

1,791

MetaboLights Database

MTBLS2267MTBLS3750MTBLS1693

UniProt Database

D5JBW8P80701Q9FH76P80702

PDBeChem Database

MYT

BRENDA Ligand Database

172767

BindingDB Database

50028166

LINCS Database

LSM-3035

Patent number

US2008076828US2008057068US2008076829

Protein Data Bank

6ma67e7f1phg4zf81w0g

ACToR Database

37245-80-054-36-4

KEGG DRUG Database

D00410

EnzymePortal Database

SABIO-RK Database

SureChEMBL Database

Reaxys Registry

CompTox Database

BKMS React Database

Molecule Details

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

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

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Metyrapone

Sigma Aldrich