metyrapone

Names

[ CAS No. ]:
54-36-4

[ Name ]:
metyrapone

[Synonym ]:
Metopyrone
Metopiron
Chlorisondamine diiodide
Mepyrapone
Metyrapone
Methopirapone
Metroprione
Methapyrapone
Metyrapon
Metopirone
Methopyrinine
Methopyrone
2-methyl-1,2-dipyridin-3-ylpropan-1-one
2-Methyl-1,2-di(pyridin-3-yl)propan-1-one
1-Propanone, 2-methyl-1,2-di-3-pyridinyl-
Methopyrapone
2-Methyl-1,2-di(3-pyridinyl)-1-propanone
2-méthyl-1,2-dipyridin-3-ylpropan-1-one
2-Methyl-1,2-dipyridin-3-ylpropan-1-on

Biological Activity

[Description]:

Metyrapone is an inhibitor of cytochrome P450-mediated ω/ω-1 hydroxylase activity and CYP11B1.Target: CYP11B1Metyrapone is a drug used in the diagnosis of adrenal insufficiency and occasionally in the treatment of Cushing's syndrome (hypercortisolism). Metyrapone blocks cortisol synthesis by reversibly inhibiting steroid 11β-hydroxylase. This stimulates ACTH secretion, which in turn increases plasma 11-Deoxycortisol levels.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Metabolic Disease

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
384.4±22.0 °C at 760 mmHg

[ Melting Point ]:
53-56ºC

[ Molecular Formula ]:
C₁₄H₁₄N₂O

[ Molecular Weight ]:
226.274

[ Flash Point ]:
189.3±28.8 °C

[ Exact Mass ]:
226.110611

[ PSA ]:
42.85000

[ LogP ]:
1.19

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.565

[ Storage condition ]:
Store at +4°C

[ Water Solubility ]:
H2O: soluble (sparingly)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UC3050000

CHEMICAL NAME :: 1-Propanone, 2-methyl-1,2-di-3-pyridyl-

CAS REGISTRY NUMBER :: 54-36-4

LAST UPDATED :: 199504

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C14-H14-N2-O

MOLECULAR WEIGHT :: 226.30

WISWESSER LINE NOTATION :: T6NJ CX1&1&V- CT6NJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 521 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 531 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 270 mg/kg

SEX/DURATION :: female 19-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - respiratory system Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2160 mg/kg

SEX/DURATION :: female 8-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2600 mg/kg

SEX/DURATION :: male 13 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 800 mg/kg

SEX/DURATION :: male 40 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 18 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 300 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 100 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: male 6 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

MUTATION DATA

TEST SYSTEM :: Mammal - dog

DOSE/DURATION :: 800 mg/kg/40D (Continuous)

REFERENCE :: FOBGA8 Folia Biologica (Krakow). (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.1- 1953- Volume(issue)/page/year: 27,277,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5298 No. of Facilities: 34 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1271 (estimated) No. of Female Employees: 660 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P301 + P312 + P330-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UC3050000

[ HS Code ]:
2933399090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Cytochrome P450-dependent metabolism of caffeine in Drosophila melanogaster.

PLoS ONE 10(2) , e0117328, (2015)

Caffeine (1, 3, 7-trimethylxanthine), an alkaloid produced by plants, has antioxidant and insecticide properties that can affect metabolism and cognition. In vertebrates, the metabolites derived from ...

The different roles of glucocorticoids in the hippocampus and hypothalamus in chronic stress-induced HPA axis hyperactivity.

PLoS ONE 9(5) , e97689, (2014)

Hypothalamus-pituitary-adrenal (HPA) hyperactivity is observed in many patients suffering from depression and the mechanism underling the dysfunction of HPA axis is not well understood. Chronic stress...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...