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Chemical Structure| 54-36-4 Chemical Structure| 54-36-4

Structure of Metyrapone
CAS No.: 54-36-4

Chemical Structure| 54-36-4

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Metyrapone is an inhibitor of cytochrome P450-mediated ω/ω-1 hydroxylase activity and CYP11B1.

Synonyms: Su-4885; NSC 25265; Metyrapone, Metopirone, SU 4885, Methbipyranone, Methopyrapone

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Product Details of Metyrapone

CAS No. :54-36-4
Formula : C14H14N2O
M.W : 226.27
SMILES Code : CC(C1=CC=CN=C1)(C)C(C2=CC=CN=C2)=O
Synonyms :
Su-4885; NSC 25265; Metyrapone, Metopirone, SU 4885, Methbipyranone, Methopyrapone
MDL No. :MFCD00006397
InChI Key :FJLBFSROUSIWMA-UHFFFAOYSA-N
Pubchem ID :4174

Safety of Metyrapone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT00004334 - Unknown - United States, Michigan ... More >> University of Michigan Health Systems Recruiting Ann Arbor, Michigan, United States, 48109 Contact: Monica N. Starkman    313-764-6168 Less <<
NCT00310427 Alcohol Dependence ... More >> Alcoholism Less << Phase 2 Completed - United States, Maryland ... More >> National Institutes of Health Clinical Center, 9000 Rockville Pike Bethesda, Maryland, United States, 20892 Less <<
NCT00310427 - Completed - -
NCT00006270 - Unknown - United States, Texas ... More >> Transitional Learning Community Galveston, Texas, United States, 77550 University of Texas Medical Branch Galveston, Texas, United States, 77555-0209 Less <<
NCT03404817 Cocaine Use Disorder Phase 1 Completed - United States, California ... More >> Collaborative Neuroscience Network, LLC Long Beach, California, United States, 90806 Less <<
NCT00426608 Depressive Disorder and Anxiet... More >>y Disorders Less << Phase 1 Completed - United Kingdom ... More >> GSK Investigational Site Cambridge, Cambridgeshire, United Kingdom, CB2 0QQ Less <<
NCT02856854 Cocaine Use Disorder Phase 1 Completed - United States, Kansas ... More >> Vince & Associates Overland Park, Kansas, United States, 66212 Less <<
NCT00033098 Cocaine-Related Disorders|Infu... More >>sions, Intravenous Less << PHASE1 UNKNOWN 2025-05-02 Cincinnati VA Medical Center, ... More >>Cincinnati, Ohio, 45220, United States Less <<
NCT01620684 Metabolic Syndrome ... More >> Obesity Insulin Resistance Less << Phase 4 Unknown - Australia, Victoria ... More >> Heart Centre, Alfred Hospital Recruiting Prahran, Melbourne, Victoria, Australia, 3181 Contact: Nora E Straznicky, BPharm PhD MPH    61 3 8532 1371    nora.straznicky@bakeridi.edu.au    Principal Investigator: Nora E Straznicky, PhD MPH Less <<
NCT00567814 Cocaine Dependence ... More >> Cocaine Addiction Less << Not Applicable Completed - United States, Louisiana ... More >> Department of Psychiatry, Psychopharmacology Research Clinic Shreveport, Louisiana, United States, 71103 Less <<
NCT02368379 Prader Willi Syndrome ... More >> Adrenal Insufficiency Less << Not Applicable Completed - United States, Ohio ... More >> Nationwide Children's Hospital Columbus, Ohio, United States, 43205 Less <<
NCT01375920 Depression Phase 3 Completed - United Kingdom ... More >> Stockton Affective Disorders Service Newcastle upon Tyne, Teesside, United Kingdom, TS17 6SD Newcastle Community Mental Health Team Newcastle Upon Tyne, Tyne and Wear, United Kingdom, NE1 4LP Regional Affective Disorders Service Newcastle Upon Tyne, Tyne and Wear, United Kingdom, NE1 4LP North Tyneside Community Mental Health Team Newcastle Upon Tyne, Tyne and Wear, United Kingdom, NE28 7PD Newcastle Magnetic Resonance Centre Newcastle Upon Tyne, Tyne and Wear, United Kingdom, NE4 5PL Bradford District Care Trust Bradford, United Kingdom Leeds Community Mental Health Team Leeds, United Kingdom, LS12 3QE Affective Disorders Service Manchester, United Kingdom, M13 9PT Manchester Community Mental Health Team Manchester, United Kingdom, M30 0GT Manchester Magnetic Resonance Centre Manchester, United Kingdom Northumberland, Tyne and Wear NHS Foundation Trust Newcastle upon Tyne, United Kingdom, NE3 3XT Less <<
NCT00125554 Major Depressive Disorder PHASE2 COMPLETED 2025-07-01 Dept. of Psychiatry and Psycho... More >>therapy, UKE, Hamburg, 20246, Germany Less <<
NCT01673087 Stress Phase 1 Completed - United States, Michigan ... More >> University of Michigan Health System Ann Arbor, Michigan, United States, 48109 Less <<
NCT02297945 Cushing's Syndrome Phase 3 Recruiting November 2018 Belgium ... More >> University hospital Antwerp Not yet recruiting Antwerp, Belgium CHU Erasme Recruiting Brussels, Belgium Contact: Driessens, Dr    +32 2 5553131       University hospital Saint Luc Recruiting Brussels, Belgium Contact: Maiter, Prof    +32 2 764 11 11       CHU Liège Recruiting Liege, Belgium Contact: Beckers, Prof    +32 4 242 52 00       Germany Charité Berlin Not yet recruiting Berlin, Germany, 10117 Contact: Tina Kienitz, Dr    +49 30 45050       Universitätsklinikum Essen Recruiting Essen, Germany Contact: Führer-Sakel, Prof    +49 201 7230       Munich university Recruiting Munich, Germany Contact: Beuschlein, Prof    +49 89 440052100       University hospital Wuerzburg Recruiting Wuerzburg, Germany Contact: Fassnacht, Prof    +49 931 2010       Hungary State health center Not yet recruiting Budapest, Hungary, 10062 Contact: Laszlo Kovacs, Dr          Contact    06 465-1800 3.       Semmelweis Egyetem II. Belgyógyászati Klinika Recruiting Budapest, Hungary Contact: Toth, Dr    +36 1 266 0926       University Debrecen Not yet recruiting Debrecen, Hungary Contact: Endre Nagy, Dr          University of Pecs Recruiting Pecs, Hungary Contact: Mezosi, Dr    +36 72 501 599       University of Szeged Not yet recruiting Szeged, Hungary Contact: Zsuzsanna Valkusz, Prof          Italy San Luigi Gonzaga Hospital, University of Turin Recruiting Orbassano, Turin, Italy, 10043 Contact: Massimo Terzolo, Prof    +39 011 90261       Grande Ospedale Metropolitano Niguarda Recruiting Milan, Italy Contact: Loli, Dr    +39 02 6444.1       Ospedale San Luca IRCCS Istituto Auxologico Italiano Recruiting Milan, Italy Contact: Cavagnini, Prof    +39 02 619111       S. Giuseppe Hospital Recruiting Milan, Italy Contact: Arosio, Dr    +39 0575 37341       Federico II University Recruiting Naples, Italy Contact: Pivonello, Prof    +39 081 253 1111       University of Padova Recruiting Padova, Italy Contact: Boscaro, Prof    +39 049 827 5111       University of Turin Recruiting Turin, Italy Contact: Ghigo, Dr    +39 011 670 6111       Poland Maria Sklodowska-Curie Memorial Cancer Center and Institute of Oncology Not yet recruiting Gliwice, Poland Contact: Barbara Jarzab, Prof          University Hospital Recruiting Krakow, Poland Contact: Motyka, Dr    +48 12 424 70 00       University Clinical Hospital Not yet recruiting Wrocław, Poland Contact: Marek Bolanowski, Prof    +48 71 327 09 00       Spain University hospital clinic of Barcelona Recruiting Barcelona, Spain Contact: Hanzu, Dr    +34 932 27 54 00       Hospital Universitario La Ribera Recruiting Valencia, Spain Contact: Fajardo, Dr    +34 962 45 81 00       Turkey Ankara Numune Training and Research Hospital Not yet recruiting Ankara, Turkey Contact: Dilek Berker, Prof          Dokuz Eylul UMF Not yet recruiting Izmir, Turkey Contact: Baris Akinci, Prof          Ondokuz Mayıs University Medical Faculty Not yet recruiting Samsun, Turkey Contact: Aysegül Atmaca, Prof          Karadeniz Teknik University Not yet recruiting Trabzon, Turkey Contact: Mustafa Koçak, Prof Less <<
NCT02406066 Cocaine Use Disorder ... More >> Tobacco Use Disorder Less << Phase 1 Completed - United States, California ... More >> Collaborative Neuroscience Network, LLC Long Beach, California, United States, 90806 United States, Louisiana Pennington Biomedical Research Center Baton Rouge, Louisiana, United States, 70808 Less <<
NCT03491696 Depressive Disorder|Hormone Di... More >>sturbance Less << PHASE4 UNKNOWN 2025-09-22 Hopitaux Universitares de Stra... More >>sbourg, Strasbourg, Bas Rhin, 67000, France|Centre Hospitalier de Rouffach, Rouffach, Haut Rhin, 68250, France Less <<
NCT06106295 Autonomous Cortisol Secretion|... More >>Mild Autonomous Cortisol Secretion (MACS) Less << PHASE2 RECRUITING 2025-01-28 Mayo Clinic Minnesota, Rochest... More >>er, Minnesota, 55905, United States Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

4.42mL

0.88mL

0.44mL

22.10mL

4.42mL

2.21mL

44.19mL

8.84mL

4.42mL

References

[1]Park H, Lee S, et al. Structural and dynamical basis of broad substrate specificity, catalytic mechanism, and inhibition of cytochrome P450 3A4. J Am Chem Soc. 2005 Oct 5;127(39):13634-42.

[2]Hays SJ, Tobes MC, et al. Structure-activity relationship study of the inhibition of adrenal cortical 11 beta-hydroxylase by new metyrapone analogues. J Med Chem. 1984 Jan;27(1):15-9.

[3]Wright MC, Paine AJ, Skett P, Auld R. Induction of rat hepatic glucocorticoid-inducible cytochrome P450 3A by metyrapone. J Steroid Biochem Mol Biol. 1994 Feb;48(2-3):271-6

[4]Drouet JB, Fauvelle F, Batandier C, Peinnequin A, Alonso A, Fidier N, Maury R, Poulet L, Buguet A, Cespuglio R, Canini F. Metyrapone effects on systemic and cerebral energy metabolism. Eur J Pharmacol. 2012 May 5;682(1-3):92-8

[5]Drouet JB, Rousset C, Maury R, Michel V, Buguet A, Cespuglio R, Canini F. Single administration of metyrapone modifies sleep-wake patterns in the rat. Eur J Pharmacol. 2011 Feb 10;652(1-3):60-4

[6]Noe S, von Werder A, Iakoubov R, Schneider H, Thaler M, Luppa P, Neu B. Dynamics of Adrenocorticotropin after Application of Metyrapone. Exp Clin Endocrinol Diabetes. 2017 Jan;125(1):53-56

[7]Winhusen T, Somoza E, Harrer JM, Moore E, Ussery T, Kropp F, Singal B, Elkashef A, Mojsiak J. Metyrapone and cocaine: a double-blind, placebo-controlled drug interaction study. Pharmacol Biochem Behav. 2005 Apr;80(4):631-8

[8]Drouet JB, Michel V, Peinnequin A, Alonso A, Fidier N, Maury R, Buguet A, Cespuglio R, Canini F. Metyrapone blunts stress-induced hyperthermia and increased locomotor activity independently of glucocorticoids and neurosteroids. Psychoneuroendocrinology. 2010 Oct;35(9):1299-310

 

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