NAV

Metyrapone

Identification

Summary

Metyraponeis a steroid 11-beta-monooxygenase inhibitor used to test hypothalamic-pituitary ACTH function.

Brand Names
Metopirone
Generic Name
Metyrapone
DrugBank Accession Number
DB01011
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
 3D
Similar Structures
Weight
Average: 226.2738
Monoisotopic: 226.11061308
Chemical Formula
C14H14N2O
Synonyms
  • Metirapona
  • Metyrapone
  • Métyrapone
  • Metyraponum

Pharmacology

Indication

Used as a diagnostic drug for testing hypothalamic-pituitary ACTH function. Occasionally used in Cushing's syndrome.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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 blockade of the enzymatic steps leading to production of cortisol and corticosterone, there is a marked increase in adrenocortical secretion of their immediate precursors, 11-desoxycortisol and desoxycorticosterone, which are weak suppressors of ACTH release, and a corresponding elevation of these steroids in the plasma and of their metabolites in the urine. These metabolites are readily determined by measuring urinary 17-hydroxycorticosteroids (17-OHCS) or 17-ketogenic steroids (17-KGS). Because of these actions, metopirone is used as a diagnostic test, with urinary 17-OHCS measured as an index of pituitary ACTH responsiveness. Metopirone may also suppress biosynthesis of aldosterone, resulting in a mild natriuresis.

Target Actions Organism
A细胞色素P450 11 b1, mitochondrial
inhibitor
 Humans
UCamphor 5-monooxygenase
other/unknown
 Pseudomonas putida
Absorption

Absorbed rapidly and well when administered orally. Peak plasma concentrations are usually reached 1 hour after administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic. The major biotransformation is reduction of the ketone to metyrapol, an active alcohol metabolite. Metyrapone and metyrapol are both conjugated with glucuronide.

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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.

Clearance

Not Available

Adverse Effects
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Toxicity

Oral LD50in 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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Abacavir Metyrapone may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib The metabolism of Abemaciclib can be increased when combined with Metyrapone.
Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Metyrapone.
Aceclofenac Aceclofenac may decrease the excretion rate of Metyrapone which could result in a higher serum level.
Acemetacin Acemetacin may decrease the excretion rate of Metyrapone which could result in a higher serum level.
Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Metyrapone.
Acetaminophen Metyrapone may increase the hepatotoxic activities of Acetaminophen.
Acetazolamide Acetazolamide may increase the excretion rate of Metyrapone which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Metyrapone which could result in a higher serum level.
Aclidinium Metyrapone may decrease the excretion rate of Aclidinium which could result in a higher serum level.
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Food Interactions
  • Take with food. Take metyrapone with milk or a snack according to the specific instructions for a single or multi-dose test.

Products

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International/Other Brands
Metopiron
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Metopirone Capsule, gelatin coated 250 mg/1 Oral Novartis Pharmaceuticals Corporation 2006-01-04 2006-01-04 US flag
Metopirone Capsule, gelatin coated 250 mg/1 Oral Novartis 1962-01-25 2012-11-30 US flag
Metopirone Capsule, gelatin coated 250 mg/1 Oral HRA Pharma Rare Diseases 1962-01-25 Not applicable US flag

Categories

ATC Codes
V04CD01 — Metyrapone
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl alkyl ketones
Alternative Parents
Pyridines and derivatives/Heteroaromatic compounds/Azacyclic compounds/Organopnictogen compounds/Organonitrogen compounds/Organic oxides/Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound/Aryl alkyl ketone/Azacycle/Heteroaromatic compound/Hydrocarbon derivative/Organic nitrogen compound/Organic oxide/Organoheterocyclic compound/Organonitrogen compound/Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ketone (CHEBI:44241)/a small molecule (CPD-7023)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
ZS9KD92H6V
CAS number
54-36-4
InChI Key
FJLBFSROUSIWMA-UHFFFAOYSA-N
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
IUPAC Name
2-methyl-1,2-bis(pyridin-3-yl)propan-1-one
SMILES
CC(C)(C(=O)C1=CN=CC=C1)C1=CC=CN=C1

References

General References
Not Available
Human Metabolome Database
HMDB0015146
KEGG Drug
D00410
KEGG Compound
C07205
PubChem Compound
4174
PubChem Substance
46504862
ChemSpider
4030
BindingDB
50028166
RxNav
6923
ChEBI
44241
ChEMBL
CHEMBL934
ZINC
ZINC000000001728
Therapeutic Targets Database
DAP000424
PharmGKB
PA450486
PDBe Ligand
MYT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Metyrapone
PDB Entries
1phg/1w0g/4zf8/6ma6/7e7f

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Recruiting Treatment Depressive Disorder/Hormone Disturbance 1
4 Unknown Status Treatment Obesity/Resistance, Insulin/Syndrome, Metabolic 1
3 Completed Treatment Cushing's Syndrome 1
3 Completed Treatment Depression 1
2 Completed Treatment Major Depressive Disorder (MDD) 1
2, 3 Recruiting Treatment Smoking, Cessation/Tobacco Use Disorders 1
1 Completed Basic Science Stress (Psychology) 1
1 Completed Diagnostic Depressive Disorder and Anxiety Disorders 1
1 Completed Treatment Cocaine Use Disorders 1
1 Completed Treatment Cocaine Use Disorders/Tobacco Use Disorders 1

Pharmacoeconomics

Manufacturers
  • 诺华制药集团
Packagers
  • Novartis AG
  • R.P. Scherer GmbH and Co. KG
Dosage Forms
Form Route Strength
Capsule Oral 250 MG
Capsule, gelatin coated Oral 250 mg/1
Capsule Oral
Prices
Unit description Cost Unit
Metopirone 250 mg capsule 3.39USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 50.5 °C PhysProp
water solubility Sparingly soluble Not Available
logP 1.8 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.427 mg/mL ALOGPS
logP 2.09 ALOGPS
logP 2.03 ChemAxon
logS -2.7 ALOGPS
pKa (Strongest Basic) 4.87 ChemAxon
Physiological Charge 0 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 42.85 Å2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 65.94 m3·mol-1 ChemAxon
Polarizability 23.98 Å3 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five Yes ChemAxon
Ghose Filter Yes ChemAxon
Veber's Rule No ChemAxon
MDDR-like Rule No ChemAxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9872
Blood Brain Barrier + 0.985
Caco-2 permeable + 0.7108
P-glycoprotein substrate Non-substrate 0.6099
P-glycoprotein inhibitor I Non-inhibitor 0.6787
P-glycoprotein inhibitor II Non-inhibitor 0.9579
Renal organic cation transporter Non-inhibitor 0.8039
CYP450 2C9 substrate Non-substrate 0.8174
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.6282
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 inhibitor Non-inhibitor 0.9071
CYP450 2D6 inhibitor Non-inhibitor 0.9484
CYP450 2C19 inhibitor Non-inhibitor 0.9026
CYP450 3A4 inhibitor Inhibitor 0.7959
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5382
Ames test Non AMES toxic 0.907
Carcinogenicity Non-carcinogens 0.8616
Biodegradation Not ready biodegradable 0.9518
Rat acute toxicity 2.6066 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9786
hERG inhibition (predictor II) Non-inhibitor 0.8202
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
GC-MS Spectrum - EI-B GC-MS splash10 - 05 - di - 8930000000 - 51278 - af0b7707c808df8
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS谱- 20 v,正面(注释d) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-004i-0090000000-c89f837f188fa67fb821
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-004i-0390000000-26267f0728adaecc8890
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-00di-0900000000-419dc733a49ddd749433
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-05fr-0900000000-7aca9c1d7ea794878775
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-05fr-1900000000-4becb55b9b4a151284ab
LC-MS/MS Spectrum - LC-ESI-IT , positive LC-MS/MS splash10-00di-0900000000-ebc70b90c01f86b98551
MS/MS Spectrum - , positive LC-MS/MS splash10-004i-1590000000-071c800b3f7a6a8740dc
MS/MS Spectrum - , positive LC-MS/MS splash10-00di-3900100000-8f8a87e8debee126c12c

Targets

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Details 1.细胞色素P450 11 b1, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
细胞色素P450 11 b1, mitochondrial
Molecular Weight
57572.44 Da
References
  1. Young EA, Ribeiro SC, Ye W: Sex differences in ACTH pulsatility following metyrapone blockade in patients with major depression. Psychoneuroendocrinology. 2007 Jun;32(5):503-7. Epub 2007 Apr 25. [Article]
  2. Johansson MK, Sanderson JT, Lund BO: Effects of 3-MeSO2-DDE and some CYP inhibitors on glucocorticoid steroidogenesis in the H295R human adrenocortical carcinoma cell line. Toxicol In Vitro. 2002 Apr;16(2):113-21. [Article]
  3. Hermansson V, Asp V, Bergman A, Bergstrom U, Brandt I: Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p'-DDD in Y-1 adrenal cells. Arch Toxicol. 2007 Nov;81(11):793-801. Epub 2007 May 9. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details 2.Camphor 5-monooxygenase
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Iron ion binding
Specific Function
Involved in a camphor oxidation system.
Gene Name
camC
Uniprot ID
P00183
Uniprot Name
Camphor 5-monooxygenase
Molecular Weight
46668.8 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Bistolas N, Christenson A, Ruzgas T, Jung C, Scheller FW, Wollenberger U: Spectroelectrochemistry of cytochrome P450cam. Biochem Biophys Res Commun. 2004 Feb 13;314(3):810-6. [Article]
  4. Shiro Y, Fujii M, Isogai Y, Adachi S, Iizuka T, Obayashi E, Makino R, Nakahara K, Shoun H: Iron-ligand structure and iron redox property of nitric oxide reductase cytochrome P450nor from Fusarium oxysporum: relevance to its NO reduction activity. Biochemistry. 1995 Jul 18;34(28):9052-8. [Article]
  5. Schunemann V, Jung C, Terner J, Trautwein AX, Weiss R: Spectroscopic studies of peroxyacetic acid reaction intermediates of cytochrome P450cam and chloroperoxidase. J Inorg Biochem. 2002 Sep 20;91(4):586-96. [Article]

Enzymes

Details 1.细胞色素P450 11 b1, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
细胞色素P450 11 b1, mitochondrial
Molecular Weight
57572.44 Da
References
  1. Johansson MK, Sanderson JT, Lund BO: Effects of 3-MeSO2-DDE and some CYP inhibitors on glucocorticoid steroidogenesis in the H295R human adrenocortical carcinoma cell line. Toxicol In Vitro. 2002 Apr;16(2):113-21. [Article]
  2. Denner K, Vogel R, Schmalix W, Doehmer J, Bernhardt R: Cloning and stable expression of the human mitochondrial cytochrome P45011B1 cDNA in V79 Chinese hamster cells and their application for testing of potential inhibitors. Pharmacogenetics. 1995 Apr;5(2):89-96. [Article]
Details 2.Cytochrome P450 2E1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
代谢几个precarcinogens、毒品和索尔vents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Heit C, Dong H, Chen Y, Thompson DC, Deitrich RA, Vasiliou VK: The role of CYP2E1 in alcohol metabolism and sensitivity in the central nervous system. Subcell Biochem. 2013;67:235-47. doi: 10.1007/978-94-007-5881-0_8. [Article]
  2. Montoliu C, Valles S, Renau-Piqueras J, Guerri C: Ethanol-induced oxygen radical formation and lipid peroxidation in rat brain: effect of chronic alcohol consumption. J Neurochem. 1994 Nov;63(5):1855-62. [Article]
Details 3.Cytochrome P450 11B2, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name
CYP11B2
Uniprot ID
P19099
Uniprot Name
Cytochrome P450 11B2, mitochondrial
Molecular Weight
57559.62 Da
References
  1. Roumen L, Sanders MP, Pieterse K, Hilbers PA, Plate R, Custers E, de Gooyer M, Smits JF, Beugels I, Emmen J, Ottenheijm HC, Leysen D, Hermans JJ: Construction of 3D models of the CYP11B family as a tool to predict ligand binding characteristics. J Comput Aided Mol Des. 2007 Aug;21(8):455-71. Epub 2007 Jul 24. [Article]
  2. Gomez-Sanchez CE, Zhou MY, Cozza EN, Morita H, Foecking MF, Gomez-Sanchez EP: Aldosterone biosynthesis in the rat brain. Endocrinology. 1997 Aug;138(8):3369-73. [Article]
Details 4.Cytochrome P450 2A6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Pelkonen O, Sotaniemi EA, Ahokas JT: Coumarin 7-hydroxylase activity in human liver microsomes. Properties of the enzyme and interspecies comparisons. Br J Clin Pharmacol. 1985 Jan;19(1):59-66. doi: 10.1111/j.1365-2125.1985.tb02613.x. [Article]
  2. Liu C, Zhuo X, Gonzalez FJ, Ding X: Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2a6: role in metabolic activation of nasal toxicants. Mol Pharmacol. 1996 Oct;50(4):781-8. [Article]
  3. Draper AJ, Madan A, Parkinson A: Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Arch Biochem Biophys. 1997 May 1;341(1):47-61. doi: 10.1006/abbi.1997.9964. [Article]
Details 5.Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 布兰登EF, Meijerman我Klijn JS窝。艾伦D, Sparidans RW, Lazaro LL, Beijnen JH, Schellens JH: In-vitro cytotoxicity of ET-743 (Trabectedin, Yondelis), a marine anti-cancer drug, in the Hep G2 cell line: influence of cytochrome P450 and phase II inhibition, and cytochrome P450 induction. Anticancer Drugs. 2005 Oct;16(9):935-43. [Article]
  2. Sevrioukova I: Interaction of Human Drug-Metabolizing CYP3A4 with Small Inhibitory Molecules. Biochemistry. 2019 Feb 19;58(7):930-939. doi: 10.1021/acs.biochem.8b01221. Epub 2019 Jan 24. [Article]
  3. Harvey JL, Paine AJ, Maurel P, Wright MC: Effect of the adrenal 11-beta-hydroxylase inhibitor metyrapone on human hepatic cytochrome P-450 expression: induction of cytochrome P-450 3A4. Drug Metab Dispos. 2000 Jan;28(1):96-101. [Article]

Transporters

Details 1.Canalicular multispecific organic anion transporter 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Teng S, Jekerle V, Piquette-Miller M: Induction of ABCC3 (MRP3) by pregnane X receptor activators. Drug Metab Dispos. 2003 Nov;31(11):1296-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:19