|Biological half-life||24 hours|
|Synonyms||Ostarine; S-22; GTx-024; MK-2866|
|Chemical and physical data|
|Molar mass||389.33 g/mol|
|3D model (Jmol)|
|Melting point||70 to 74 °C (158 to 165 °F)|
Enobosarm, also known as ostarine, 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.
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." While GTx has not formally disclosed the structure of ostarine, the chemical composition of ostarine is revealed in patent databases such the WIPO and discussed by Zhang et al., 2009 in the primary literature. 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. 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.
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.
In June 2015 Azerbaijan's Chaltu Beji tested positive for doping at the 2015 European Games in Baku. The 18-year-old Ethiopian-born Beji tested positive for the banned substance Ostarine in a urine sample with a B sample confirming the result. She won the 3,000-meter steeplechase event despite falling at the last water jump, she was disqualified because of the positive tests.
In May 2016, Romanian-Canadian professional boxer Lucian Bute, former super middleweight world titleholder, tested positive for Ostarine after his draw against Swedish professional boxer and titleholder Badou Jack on April 30 at the D.C. Armory in Washington, D.C.
On December 16, 2016, Russian heavyweight boxer Alexandre Povetkin tested positive for Ostarine less than a day before an interim WBC title fight against former WBC champ Bermane Stiverne. The fight, which was scheduled for December 17 in Yekaterinburg, Russia, was cancelled.
In March 2016, Australian triathlete Lisa Marangon received a 4-year ban ending in March 2020 for use of banned substance Ostarine. American triathlete Ashley Paulson was given a 6-month suspension for use of banned substance Ostarine because officials accepted her contention that the banned drug positive came from a contaminated supplement.
In February 2017, American triathlete Beth Gerdes was given a 2-year suspension for presence of ostarine, and American triathlete Lauren Barnett was given a 6-month suspension for the presence of Ostarine. Both triathletes claimed contamination from salt tablet supplements. Lauren Barnett was able to provide tablets and sealed bottle tablets which both tested positive for contamination, thus only the 6-month suspension. The 2-year suspension still stands for Beth Gerdes who provided tablets for testing, but tests showed only low levels of ostarine not high enough to confirm the finding. .
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- James T. Dalton, Duane D. Miller, Donghua Yin, Yali He. Selective androgen receptor modulators and methods of use thereof. US Patent 6569896
- 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.
- 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
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- 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
- 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
- "Russian boxer Povetkin tests positive, fight with Canadian Stiverne cancelled – WBC". RT International. Retrieved 2016-12-17.