Stanozolol

Stanozolol
Systematic (IUPAC) name
(1S,3aS,3bR,5aS,10aS,10bS,12aS)-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol
Clinical data
AHFS/Drugs.com Multum Consumer Information
Pregnancy cat. X
Legal status Prescription only
(US)
Routes Oral, Intramuscular
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life 1 day
Excretion Renal: 84%
Identifiers
CAS number 10418-03-8 N
ATC code A14AA02
PubChem CID 25249
DrugBank DB06718
ChemSpider 23582 Y
UNII 4R1VB9P8V3 Y
KEGG D00444 Y
ChEMBL CHEMBL1200324 N
Chemical data
Formula C21H32N2O 
Mol. mass 328.49
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Stanozolol, commonly sold under the name Winstrol (oral), Tenabol and Winstrol Depot (intramuscular), was developed by Winthrop Laboratories in 1962. It is a synthetic anabolic steroid derived from testosterone, and has been approved by the FDA for human use.

Unlike most injectable anabolic steroids, stanozolol is not esterified and is sold as an aqueous suspension, or in oral tablet form. The drug has a high oral bioavailability, due to a C17 α-alkylation which allows the hormone to survive first-pass liver metabolism when ingested. It is because of this that stanozolol is also sold in tablet form.

Stanozolol is usually considered a safer choice for female bodybuilders in that its anabolic effects predominate over its androgenic effects, although virilization and masculinization are still very common even at low doses.

Stanozolol has been used in both animal and human patients for a number of conditions. In humans, it has been demonstrated to be successful in treating anaemia and hereditary angioedema. Veterinarians may prescribe the drug to improve muscle growth, red blood cell production, increase bone density and stimulate the appetite of debilitated or weakened animals.

Stanozolol is one of the anabolic steroids commonly used as a performance enhancing drug and is banned from use in sports competition under the auspices of the International Association of Athletics Federations (IAAF) and many other sporting bodies. Stanozolol has also been used in US horse racing.[1]

Contents

Use in bodybuilding

In bodybuilding, stanozolol is typically "stacked" with other testosterone-based anabolic steroids. Stanozolol is preferred by many steroid users due to the fact that it causes strength increases without excess weight-gain, promotes increases in vascularity, and will not convert to estrogen. It also does not cause excess water retention, and is thought to have a diuretic effect on the body.

Stanozolol is commonly used by athletes and bodybuilders alike to lose fat while retaining lean body mass. It is usually used in a "cutting cycle", to help preserve lean body mass while metabolizing adipose, although it has not been proven conclusively that it has any special fat-burning properties.

It is presented most commonly as a 50 mg/mL injection or a 5 mg tablet. However, recently 100 mg/mL versions have become available. A common dosage can be 10–25 mg/day orally and 25–50 mg daily injected, with optimal results usually seen at 50 mg/day. It is reduced to micrometer particles in aqueous suspension and does not have a typical elimination half-life. Authentic stanozolol can easily be seen, because it will separate in its container if left undisturbed for a number of hours (the micronized crystal will fall to the bottom, and the water suspension will rise to the top). It has a white, milky color.

An alternative to stanozolol is furazabol. Furazabol's effects are virtually identical to stanozolol except that instead of having an extremely adverse effect on cholesterol values, furazabol actually improves a person's blood lipid profile (at therapeutic doses, not performance enhancing ones). Sold under the trade name Miotolan, Furazabol is a standard treatment in Japan for hyperlipemia.

Detection of use

Stanozolol is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary metabolites are unique to stanozolol and are detectable in the urine for up to 10 days after a single 5-10 mg oral dose. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry.[2][3][4]

Law

In the United States, like other anabolic steroids, stanozolol is classified as a controlled substance under federal regulation. In New York, the state legislature classifies anabolic steroids under DEA Schedule III.

Publicized abuse cases

Chemistry

The pyrazole ring in stanozolol can be prepared by the condensation of a keto-aldehyde with hydrazine.[21]

References

  1. ^ Win, Place, and Dope Slate, May 1, 2009
  2. ^ Mateus-Avois L, Mangin P, Saugy M. Use of ion trap gas chromatography-multiple mass spectrometry for the detection and confirmation of 3'hydroxystanozolol at trace levels in urine for doping control. J. Chromatogr. B 816: 193-201, 2005.
  3. ^ Pozo OJ, Van Eenoo P, Deventer K et al. Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry. Steroids 74: 837-852, 2009.
  4. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1442-1443.
  5. ^ "The most corrupt race ever". Guardian Unlimited (London). August 1, 2004. http://observer.guardian.co.uk/osm/story/0,,1270863,00.html. Retrieved May 24, 2010 
  6. ^ Ivanova Sets First Record in Helsinki The Moscow Times.com, 8-8-2005
  7. ^ WOMEN'S SHOT-PUT CHAMPION BARRED FOR LIFE The New York Times, June 2, 2004
  8. ^ Blonska Thrown Out of Long Jump BBC Sport, August 21, 2008
  9. ^ Ukrainian Blonska Given Life Ban BBC Sport, August 29, 2008
  10. ^ Jenkins, Lee (August 3, 2005). "Popular Steroid Is at the Center of Palmeiro's Case". The New York Times. http://www.nytimes.com/2005/08/03/sports/baseball/03steroids.html?ei=5090&en=c52da2e558ba4e10&ex=1280721600&partner=rssuserland&emc=rss&pagewanted=print. Retrieved May 24, 2010. 
  11. ^ Bonds exposed: Shadows details superstar slugger's steroid use, Sports Illustrated, March 7, 2006
  12. ^ "CAS 2006/A/1149 WADA v/ FMF & José Salvador Carmona Alvarez", May 16, 2007 Accessed May 17, 2007
  13. ^ Carson, Alan (June 30, 2009). "Ex-Celt ace Hedman faces Steroids rap". The Sun. http://www.thesun.co.uk/scotsol/homepage/news/2507007/Magnus-Hedman-is-charged-with-the-use-of-a-banned-steroid.html. Retrieved November 3, 2010. 
  14. ^ Ken Pishna (2007-07-03). "Breaking News: Phil Baroni Tests Positive". MMAWeekly.com. http://www.mmaweekly.com/absolutenm/templates/dailynews.asp?articleid=4262&zoneid=13. Retrieved 2007-07-03. 
  15. ^ "Two Positive at K-1 World GP Vegas". Nokaut. August 17, 2007. http://www.nokaut.com/?id=12&solo_news=997&lang=e&cur=eur. Retrieved 2007-08-17. 
  16. ^ All-Star Roster Shows Up on Mitchell Report washingtonpost.com, 12-13-2007
  17. ^ Bossert, Jerry; Red, Christian (May 16, 2008). "Big Brown's legal doping a concern". Daily News (New York). http://www.nydailynews.com/sports/more_sports/2008/05/15/2008-05-15_big_browns_legal_doping_a_concern.html?print=1&page=all. 
  18. ^ http://mma-live.com/chris-leben-fails-ufc-89-drug-test/
  19. ^ Sidelnikov Suspended for Steroid Use sherdog.com, 03-03-2009
  20. ^ [1] sherdog.com, 10-13-2003
  21. ^ Clinton, R. O.; Manson, A. J.; Stonner, F. W.; Beyler, A. L.; Potts, G. O.; Arnold, A. (1959). J. Amer. Chem. Soc. 81 (6): 1513. doi:10.1021/ja01515a060.