Enobosarm (also known as Ostarine, GTx-024 and MK-2866)

Martin Maric, the 2009 NCAA discus champion for the University of California in Berkeley, was suspended for using Ostarine on October 1, 2014.

Enobosarm
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Enobosarm

Systematic (IUPAC) name
((2S)-3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide)
Clinical data
Legal status
Investigational new drug
Routes Oral
Pharmacokinetic data
Half-life 24 hours[citation needed]
Identifiers
CAS number 841205-47-8
ATC code None
PubChem CID 10181786
Chemical data
Formula C19H14F3N3O3
Mol. mass 389.33 g/mol
SMILES[show]
Physical data
Melt. point 70–74 °C (158–165 °F)
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Enobosarm ((2S)-3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide) (also known as Ostarine, GTx-024 and MK-2866) is an investigational selective androgen receptor modulator (SARM) from GTX, Inc for treatment of conditions such as muscle wasting and osteoporosis, formerly under development by Merck & Company.[1]

Structure[edit]

Ostarine versus andarine
According to a recent paper authored by GTx, "Readers are cautioned to note that the name Ostarine is often mistakenly linked to the chemical structure of [S-4], which is also known as andarine. The chemical structure of Ostarine has not been publicly disclosed."[2] While GTx has not formally disclosed the structure of Ostarine, the chemical composition of Ostarine is revealed in patent databases such the WIPO[3] and discussed by Zhang et al., 2009 in the primary literature.[4] Various SARM chemotypes exist (aryl propionamides, quinolines, quinolinones, bicyclic hydantoins), though aryl propionamides such as Ostarine, Andarine/S-4, and S-23 represent some of the most advanced putative therapeutics under investigation.[5] In terms of atom connectivity, Enobosarm differs from Andarine by cyano substitutions on the phenyl rings as it replaces both the nitro and acetamido moieties.

Doping[edit]
Selective androgen receptor modulators may be used by athletes to assist in training and increase physical stamina and fitness, potentially producing effects similar to anabolic steroids. For this reason, SARMs were banned by the World Anti-Doping Agency in January 2008 despite no drugs from this class yet being in clinical use, and blood tests for all known SARMs have been developed.[6][7]

In June 2013, professional cyclist Nikita Novikov was provisionally suspended after a possible breach of anti-doping rules, due to a positive A-sample result for Ostarine. [8]

References[edit]
Jump up ^ James T. Dalton, Duane D. Miller, Donghua Yin, Yali He. Selective androgen receptor modulators and methods of use thereof. US Patent 6569896
Jump up ^ Mohler ML, Bohl CE, Jones A, et al. (June 2009). "Nonsteroidal selective androgen receptor modulators (SARMs): dissociating the anabolic and androgenic activities of the androgen receptor for therapeutic benefit". J. Med. Chem. 52 (12): 3597–617. doi:10.1021/jm900280m. PMID 19432422.
Jump up ^ WO application 2008127717, James T. Dalton and Duane D. Miller, "Selective Androgen Receptor Modulators for Treating Diabetes", published Oct 23, 2008, assigned to University of Tennessee Research Foundation, James T. Dalton, and Duane D. Miller
Jump up ^ Zhang X, Lanter JC, Sui Z (September 2009). "Recent advances in the development of selective androgen receptor modulators". Expert Opin Ther Pat 19 (9): 1239–58. doi:10.1517/13543770902994397. PMID 19505196.
Jump up ^ Jones A, Chen J, Hwang DJ, Miller DD, Dalton JT (January 2009). "Preclinical characterization of a (S)-N-(4-cyano-3-trifluoromethyl-phenyl)-3-(3-fluoro, 4-chlorophenoxy)-2-hydroxy-2-methyl-propanamide: a selective androgen receptor modulator for hormonal male contraception". Endocrinology 150 (1): 385–95. doi:10.1210/en.2008-0674. PMC 2630904. PMID 18772237.
Jump up ^ Thevis M, Kohler M, Schlörer N, Kamber M, Kühn A, Linscheid MW, Schänzer W. Mass spectrometry of hydantoin-derived selective androgen receptor modulators. Journal of Mass Spectrometry. 2008 May;43(5):639-50. PMID 18095383
Jump up ^ Thevis M, Kohler M, Thomas A, Maurer J, Schlörer N, Kamber M, Schänzer W. Determination of benzimidazole- and bicyclic hydantoin-derived selective androgen receptor antagonists and agonists in human urine using LC-MS/MS. Analytical and Bioanalytical Chemistry. 2008 May;391(1):251-61. PMID 18270691
Jump up ^ http://www.vacansoleildcm.co.uk/nieuws/nikita-novikov-provisionally-suspended-after-possible-breach-of-anti-doping-rules.html