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Enobosarm

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Enobosarm
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Investigational new drug
Pharmacokinetic data
Elimination half-life4 hours
Identifiers
  • (S)-3-(4-acetylamino-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H18F3N3O6
Molar mass441.357 g/mol g·mol−1
3D model (JSmol)
Melting point70 to 74 °C (158 to 165 °F)
  • O=N(=O)c1ccc(cc1C(F)(F)F)NC(=O)C(O)(C)COc2ccc(cc2)NC(C)=O

Ostarine is an investigational selective androgen receptor modulator (SARM) developed by GTx Inc for treatment of conditions such as muscle wasting and osteoporosis.[1] Treatment with exogenous testosterone is effective in counteracting these symptoms but is associated with a range of side effects, the most serious of which is enlargement of the prostate gland, which can lead to benign prostatic hypertrophy and even prostate cancer. This means there is a clinical need for selective androgen receptor modulators, which produce anabolic effects in some tissues such as muscle and bone, but without stimulating androgen receptors in the prostate.[2] Ostarine was one of the first SARMs to be developed,[3] using the non-steroidal androgen antagonist bicalutamide as a lead compound.[4]

To correct errors formerly found on this page, and still on others websites, Ostarine is NOT S-4, nor is Ostarine also known as Acetamidoxolutamide, nor is it the compound structure listed to the left which IS S-4. While Ostarine is very close chemically to S-4, please note that S-4 failed in early safety trials.

Ostarine is an orally active, potent and selective agonist for androgen receptors which was shown in animal studies to have anabolic effects in both muscle and bone tissue, but with no measurable effect on lutenizing hormone or follicle-stimulating hormone levels at the dose range tested, although it did increase prostate weight, with an androgenic potency around 1/3rd of its anabolic potency. It was shown in vitro to increase the ratio of osteoblast formation from bone marrow osteoprogenitor cells, and reduced the number of new osteoclasts formed. It produced dose-dependent increases in bone mineral density and mechanical strength in vivo, as well as decreasing body fat and increasing lean body mass.[5] However while human trials have shown evidence of similar efficacy, ostarine has a short half-life in humans of only 4 hours,[6] and while ostarine has gone through human trials up to Phase II with positive results,[7] longer acting analogues are currently in development which may be more suitable for clinical use.

Selective androgen receptor modulators may also be used by athletes to assist in training and increase physical stamina and fitness, potentially producing effects similar to anabolic steroids but with significantly less side effects. For this reason, SARMs have already been banned by the World Anti-Doping Agency since January 2008 despite no drugs from this class yet being in clinical use, and blood tests for all known SARMs are currently being developed.[8][9]

References

  1. ^ James T. Dalton, Duane D. Miller, Donghua Yin, Yali He. Selective androgen receptor modulators and methods of use thereof. US Patent 6569896
  2. ^ Gao W, Dalton JT. Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs). Drug Discovery Today. 2007 Mar;12(5-6):241-8. PMID 17331889
  3. ^ Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT. Pharmacodynamics of selective androgen receptor modulators. Journal of Pharmacology and Experimental Therapeutics. 2003 Mar;304(3):1334-40. PMID 12604714
  4. ^ Chen J, Kim J, Dalton JT. Discovery and therapeutic promise of selective androgen receptor modulators. Molecular Interventions. 2005 Jun;5(3):173-88. PMID 15994457
  5. ^ Kearbey JD, Gao W, Narayanan R, Fisher SJ, Wu D, Miller DD, Dalton JT. Selective Androgen Receptor Modulator (SARM) treatment prevents bone loss and reduces body fat in ovariectomized rats. Pharmaceutical Research. 2007 Feb;24(2):328-35. PMID 17063395
  6. ^ Gao W, Kim J, Dalton JT. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharmaceutical Research. 2006 Aug;23(8):1641-58. PMID 16841196
  7. ^ GTx Announces That Ostarine Achieved Primary Endpoint Of Lean Body Mass And A Secondary Endpoint Of Improved Functional Performance
  8. ^ 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
  9. ^ 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


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