Metribolone

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Metribolone
Metribolone.png
Methyltrienolone-1E3G-3D-balls.png
Names
IUPAC name
17β-17-Hydroxy-17-methyl-estra-4,9,11-trien-3-one
Other names
Methyltrienolone, R1881
Identifiers
965-93-5 YesY
ChEBI CHEBI:379896 N
ChEMBL ChEMBL166444 YesY
ChemSpider 229099 N
2857
Jmol 3D model Interactive image
KEGG C14257 N
MeSH D015741
PubChem 261000
UNII 2C323EGI97 N
Properties
C19H24O2
Molar mass 284.39266
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Metribolone (INN) (developmental code names R1881, NSC-92858E), also known as methyltrienolone, is a potent, non-aromatizable anabolic-androgenic steroid[1] which was never marketed for clinical use but has been used in scientific research as a photoaffinity label for the androgen receptor.[2] It is the 17α-methylated derivative of trenbolone, and is a similarly potent anabolic steroid, but with high hepatotoxicity.[3] Metribolone binds with high affinity not only to the androgen receptor, but also to the progesterone receptor, and binds to the glucocorticoid receptor as well.[4][5]

11 members of the Greek national weightlifting team and 4 Greek track and field athletes tested positive with methyltrienolone prior to the 2008 Beijing Olympic Games.[6]

References[edit]

  1. ^ Bojar H, Maar K, Staib W (1980). "The endocrine background of human renal cell carcinoma. V. Binding of the highly potent androgen methyltrienolone (R 1881) by tumour cytosol". Urologia Internationalis 35 (2): 154–60. doi:10.1159/000280315. PMID 6966435. 
  2. ^ Brinkmann AO, Kuiper GG, de Boer W, Mulder E, Bolt J, van Steenbrugge GJ, van der Molen HJ (January 1986). "Characterization of androgen receptors after photoaffinity labelling with [3H]methyltrienolone (R1881)". Journal of Steroid Biochemistry 24 (1): 245–9. doi:10.1016/0022-4731(86)90058-0. PMID 2422446. 
  3. ^ Krüskemper HL, Noell G (July 1966). "Liver toxicity of a new anabolic agent: methyltrienolone (17-alpha-methyl-4,9,11-estratriene-17 beta-ol-3-one)". Steroids 8 (1): 13–24. doi:10.1016/0039-128x(66)90114-0. PMID 5955468. 
  4. ^ Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Current Medicinal Chemistry 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363. 
  5. ^ Ho-Kim MA, Tremblay RR, Dubé JY (November 1981). "Binding of methyltrienolone to glucocorticoid receptors in rat muscle cytosol". Endocrinology 109 (5): 1418–23. doi:10.1210/endo-109-5-1418. PMID 6975208. 
  6. ^ "Eleven Greek weightlifters test positive; coach suspended". Associated Press / USATODAY.com. 2008-04-04. Retrieved 2009-06-28. 

External links[edit]