Metyrapone

Metyrapone

Systematic (IUPAC) name
2-methyl-1,2-di(pyridin-3-yl)propan-1-one
Clinical data
Trade names	Metopirone
AHFS/Drugs.com	Consumer Drug Information
Pregnancy cat.	C US
Legal status	?
Routes	Oral
Pharmacokinetic data
Half-life	1.9 ±0.7 hours.
Identifiers
CAS number	54-36-4 Y
ATC code	V04CD01
PubChem	CID 4174
DrugBank	APRD01111
ChemSpider	4030 Y
UNII	ZS9KD92H6V Y
KEGG	D00410 Y
ChEBI	CHEBI:44241 N
ChEMBL	CHEMBL934 Y
Chemical data
Formula	C14H14N2O
Mol. mass	226.274 g/mol
SMILES	eMolecules & PubChem
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 Y Key:FJLBFSROUSIWMA-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Metyrapone (trade name Metopirone) is a drug used in the diagnosis of adrenal insufficiency and occasionally in the treatment of Cushing's syndrome (hypercortisolism).

Mechanism

Metyrapone blocks cortisol synthesis^[1] by inhibiting steroid 11β-hydroxylase. This stimulates ACTH secretion, which in turn increases plasma 11-deoxycortisol levels. When excess ACTH secretion is the cause of hypercortisolism, the metyrapone test helps clarify if the source of the ACTH is pituitary or ectopic (non-pituitary).

Uses

Metyrapone can be used in the diagnosis of adrenal insufficiency. Metyrapone 30mg/kg, maximum dose 3000 mg, is administered at midnight usually with a snack. The plasma cortisol and 11-deoxycortisol are measured the next morning between 8:00 and 9:00 am. A plasma cortisol less than 220nmol/l indicates adequate inhibition of 11β-hydroxylase. In patients with intact Hypothalamo-pituitary-adrenal axis, CRH and ACTH levels rise as a response to the falling cortisol levels. This results in an increase of the steroid precursors in the pathway. Therefore if 11-deoxycortisol levels do not rise and remains less than 7 mcg/dl and ACTH rises, then it is highly suggestive of impaired adrenal insufficiency, if neither 11-deoxycortisol nor ACTH rise it is highly suggestive of an impaired HPA axis at either the pituitary or hypothalamus.

Metyrapone test may aid in verifying the cause of Cushing's syndrome. Most patients with pituitary dysfunction and/or pituitary microadenoma will increase ACTH secretion in response to metyrapone, while most ectopic ACTH-producing tumors will not. Pituitary macroadenomas do not always respond to metyrapone.

Experimental use

Metyrapone has been found in early human trials to reduce recollection of emotional memories in normal volunteers. The volunteers showed significant impairment in ability to retrieve memories with negative emotional content while not impairing memories with neutral content. This has significant implication in the study of the process of emotional healing in post traumatic stress disorder.^[2][3]

References

1. ^ Young EA, Ribeiro SC, Ye W (June 2007). "Sex Differences in ACTH Pulsatility following Metyrapone Blockade in Patients with Major Depression". Psychoneuroendocrinology 32 (5): 503–7. doi:10.1016/j.psyneuen.2007.03.003. PMC 1975691. PMID 17462829. http://linkinghub.elsevier.com/retrieve/pii/S0306-4530(07)00061-3. 
2. ^ University of Montreal (27 May 2011). "Drug may help overwrite bad memories". Science Daily (online: ScienceDaily). http://www.sciencedaily.com/releases/2011/05/110526064802.htm. Retrieved 27 May 2011. 
3. ^ Marin, Marie-Frances; A. Hupbach, F. S. Maheu, K. Nader, S. J. Lupien. "Metyrapone Administration Reduces the Strength of an Emotional Memory Trace in a Long-Lasting Manner". Journal of Clinical Endocrinology & Metabolism early release abstract (8): E1221. doi:10.1210/jc.2011-0226. 

See also

• ACTH stimulation test

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.v · Categories: Antiglucocorticoids Pyridines Pharmacology stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем написать курсовую Revolutionary Communist Party of India Watchdog timer Look at other dictionaries: metyrapone — An inhibitor of adrenocortical steroid C 11 β hydroxylation, administered orally or intravenously to determine the ability of the pituitary gland to increase its secretion of corticotropin; because 11 deoxycorticosteroids, as a consequence of m.… …   Medical dictionary metyrapone test — (for Cushing syndrome) plasma 11 deoxycortisol or urinary 17 hydroxycorticosteroids are measured after the administration of metyrapone; levels are increased in patients with Cushing disease but not in patients with ectopic ACTH syndrome …   Medical dictionary metyrapone — noun A drug used in the control of hypercortisolism …   Wiktionary metyrapone — me·tyr·a·pone …   English syllables metyrapone — n. a drug that interferes with the production of the hormones cortisol and aldosterone and is used in the diagnosis and treatment of Cushing s syndrome. It is administered by mouth. Side effects may include nausea, vomiting, low blood pressure,… …   The new mediacal dictionary metyrapone — məˈtirəˌpōn noun ( s) Etymology: methyl + rapone (perhaps alteration of propanone) : a metabolic hormone C14H14N2O that inhibits biosynthesis of cortisol and corticosterone and is used to test for normal functioning of the pituitary gland …   Useful english dictionary Метирапон (Metyrapone) — лекарственное вещество, влияющее на выработку в организме человека гормона альдостерона; применяется для лечения синдрома Кушинга. Назначается внутрь. Возможные побочные эффекты: тошнота, рвота, снижение кровяного давления и аллергические реакции …   Медицинские термины МЕТИРАПОН — (metyrapone) лекарственное вещество, влияющее на выработку в организме человека гормона альдостерона; применяется для лечения синдрома Кушинга. Назначается внутрь. Возможные побочные эффекты: тошнота, рвота, снижение кровяного давления и… …   Толковый словарь по медицине Critical illness-related corticosteroid insufficiency — (CIRCI) is a form of adrenal insufficiency in critically ill patients who have blood corticosteroid levels which are inadequate for the severe stress response they experience. Combined with decreased glucocorticoid receptor sensitivity and tissue …   Wikipedia Cyproterone — and its acetate Systematic (IUPAC) name 6 chloro 1β,2β dihydro 17 hydroxy 3′H cyclopropa[1,2]pregna 4,6 diene …   Wikipedia 18+ © Academic, 2000-2025 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”