M2696

Metyrapone

Name: Metyrapone
Brand: SIGMA

≥98% (HPLC), glucocorticoid synthesis inhibitor, solid

Sinónimos:

Su-4885

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About This Item

Fórmula empírica (notación de Hill):

C₁₄H₁₄N₂O

Número CAS:

54-36-4

Peso molecular:

226.27

NACRES:

NA.77

PubChem Substance ID:

329817949

UNSPSC Code:

51111800

EC Number:

200-206-2

MDL number:

MFCD00006397

Beilstein/REAXYS Number:

163023

Nombre del producto

Metyrapone, ≥98% (HPLC), solid

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

SMILES string

CC(C)(c1cccnc1)C(=O)c2cccnc2

InChI key

FJLBFSROUSIWMA-UHFFFAOYSA-N

sterility

non-sterile

assay

≥98% (HPLC)

form

solid

technique(s)

toxicology assay: suitable

mp

52-55 °C (lit.)

solubility

H₂O: <2 mg/mL
DMSO: >20 mg/mL

originator

Novartis

shipped in

ambient

storage temp.

room temp

Quality Level

100

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Categorías relacionadas

Pequeñas moléculas bioactivas

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.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Some dystrophy phenotypes of dystrophin-deficient mdx mice are exacerbated by mild, repetitive daily stress.

Angus Lindsay et al.

FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 35(4), e21489-e21489 (2021-03-19)

Psychosocial stressors can cause physical inactivity, cardiac damage, and hypotension-induced death in the mdx mouse model of Duchenne muscular dystrophy (DMD). Because repeated exposure to mild stress can lead to habituation in wild-type mice, we investigated the response of mdx

A facilitative role for corticosterone in the acquisition of a spatial task under moderate stress.

Irit Akirav et al.

Learning & memory (Cold Spring Harbor, N.Y.), 11(2), 188-195 (2004-04-01)

Emotionally charged experiences alter memory storage via the activation of hormonal systems. Previously, we have shown that compared with rats trained for a massed spatial learning task in the water maze in warm water (25 degrees C), animals that were

Pathophysiology of hypercortisolism in depression: pituitary and adrenal responses to low glucocorticoid feedback.

B J Carroll et al.

Acta psychiatrica Scandinavica, 125(6), 478-491 (2012-01-04)

To test three theories of hypercortisolemia in depression-hypothalamic overdrive, impaired glucocorticoid feedback, or autonomous cortisol production. We applied an overnight low-cortisol feedback strategy by administering metyrapone to hypercortisolemic depressed in-patients and control subjects. Under metyrapone, the increases of plasma adrenocorticotropic

Interactions between cortisol and Rhesus glycoprotein expression in ureogenic toadfish, Opsanus beta.

Tamara M Rodela et al.

The Journal of experimental biology, 215(Pt 2), 314-323 (2011-12-23)

In their native environment, gulf toadfish excrete equal quantities of ammonia and urea. However, upon exposure to stressful conditions in the laboratory (i.e. crowding, confinement or air exposure), toadfish decrease branchial ammonia excretion and become ureotelic. The objective of this

Acute stress-induced sensitization of the pituitary-adrenal response to heterotypic stressors: independence of glucocorticoid release and activation of CRH1 receptors.

Xavier Belda et al.

Hormones and behavior, 62(4), 515-524 (2012-09-19)

A single exposure to some severe stressors causes sensitization of the hypothalamic-pituitary-adrenal (HPA) response to novel stressors. However, the putative factors involved in stress-induced sensitization are not known. In the present work we studied in adult male rats the possible

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