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PubChem
| Name: | Metyrapone |
|---|---|
| PubChem Compound ID: | 120837 |
| 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. |
| Molecular formula: | C18H20N2O7 |
| Molecular weight: | 376.361 g/mol |
| Synonyms: |
1-Propanone, 2-methyl-1,2-di-3-pyridyl-, ditartrate (6IC); Metopirone ditartrate; Metopirone tartrate; Metyrapone tartrate [USAN]; Metyrapone ditartrate; 1-Propanone, 2-methyl-1,2-di-3-pyridyl-, tartrate (1:2); 1-Propanone, 2-methyl-1,2-di-3-pyridinyl-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:2); Metyrapone tartrate; 2-Methyl-1,2-dipyridyl-3'-1-oxopropane ditartrate; Su 4885.
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DrugBank
Identification
| Name: | Metyrapone |
|---|---|
| Name (isomeric): | DB01011 |
| Drug Type: | small molecule |
| 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. |
| Synonyms: |
Methopyrone; Methbipyranone; Mepyrapone; Methopirapone; Methopyrapone; Metroprione; Methopyrinine; Metyrapon; Methapyrapone
|
| Brand: | Metopiron, Metapirone, Metapyron, Metopyrone, Metopirone, Metapyrone |
| Category: | Antimetabolites, Enzyme Inhibitors |
| CAS number: | 54-36-4 |
Pharmacology
| 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. |
| Mechanism of Action: |
The pharmacological effect of Metopirone is to reduce cortisol and corticosterone production by inhibiting the 11-ß-hydroxylation reaction in the adrenal cortex. Removal of the strong inhibitory feedback mechanism exerted by cortisol results in an increase in adrenocorticotropic hormone (ACTH) production by the pituitary. With continued block...
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| Absorption: | Absorbed rapidly and well when administered orally. Peak plasma concentrations are usually reached 1 hour after administration. |
| Biotransformation: | Hepatic. The major biotransformation is reduction of the ketone to metyrapol, an active alcohol metabolite. Metyrapone and metyrapol are both conjugated with glucuronide. |
| Route of 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. |
| Half Life: | 1.9 ±0.7 hours. |
| 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 |
Interactions
| Drug interaction: |
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Targets
Enzymes
Transporters
