Enobosarm

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Enobosarm
Ostarine.svg
Clinical data
Synonyms Ostarine; S-22; GTx-024;[1] MK-2866
Routes of
administration
By mouth
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Biological half-life 24 hours[citation needed]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
Formula C19H14F3N3O3
Molar mass 389.33 g/mol
3D model (JSmol)
Melting point 132 to 136 °C (270 to 277 °F)
  (verify)

Enobosarm, also known as ostarine, is an investigational selective androgen receptor modulator (SARM) developed by GTX, Inc for the treatment of conditions such as muscle wasting and osteoporosis, formerly under development by Merck & Company.[2]

Chemistry[edit]

Structure[edit]

Enobosarm versus andarine

According to a 2009 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."[3] While GTx has not formally disclosed the structure of enobosarm, the chemical composition of enobosarm is revealed in patent databases such the WIPO[4] and discussed by Zhang et al., 2009 in the primary literature.[5] Various SARM chemotypes exist (aryl propionamides, quinolines, quinolinones, bicyclic hydantoins), though aryl propionamides such as enobosarm, andarine/S-4, and S-23 represent some of the most advanced putative therapeutics under investigation.[6] 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.

Society and culture[edit]

Doping in sports[edit]

SARMs including enobosarm may be and have been 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.[7][8] There are a variety of known cases of doping in sports with enobosarm by professional athletes.

Recalls[edit]

May 2017: Dynamic Technical Formulations LLC. is voluntarily recalling all lots of Tri-Ton, a dietary supplement found to contain enobosarm and andarine.[9]

See also[edit]

References[edit]

  1. ^ Srinath R, Dobs A (2014). "Enobosarm (GTx-024, S-22): a potential treatment for cachexia". Future Oncol. 10 (2): 187–94. doi:10.2217/fon.13.273. PMID 24490605. 
  2. ^ James T. Dalton, Duane D. Miller, Donghua Yin, Yali He. Selective androgen receptor modulators and methods of use thereof. US Patent 6569896
  3. ^ 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. 
  4. ^ 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 
  5. ^ 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. 
  6. ^ 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 2630904Freely accessible. PMID 18772237. 
  7. ^ 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
  8. ^ 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
  9. ^ https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm559907.htm

External links[edit]