Stanozolol

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Stanozolol
Stanozolol.svg
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 YesY
UNII 4R1VB9P8V3 YesY
KEGG D00444 YesY
ChEBI CHEBI:9249 N
ChEMBL CHEMBL1200324 N
Chemical data
Formula C21H32N2O 
Mol. mass 328.49
 N (what is this?)  (verify)

Stanozolol, commonly sold under the name Winstrol (oral) and Winstrol Depot (intramuscular), is a synthetic anabolic steroid derived from dihydrotestosterone. It was developed by Winthrop Laboratories (Sterling Drug) in 1962, 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 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 performance enhancing drugs and is banned from use in sports competition under the auspices of the International Association of Athletics Federations (IAAF) and many other sporting bodies. Additionally, stanozolol has been used in US horse racing.[1]

Use in bodybuilding[edit]

Seized stanozolol tablets.

Stanozolol is subject to non-medically supervised off-label use by some athletes for its anabolic properties frequently presenting with concomitant reduction of body fat. Stanozolol is a modified derivative of dihydrotestosterone (DHT) and thus not aromatized to oestrogens via the aromatase class of enzymes (see chemical structure to right). Bodybuilders frequently misuse the term "dry" in describing their joint pain while using stanozolol either orally or via IM injection of an aqueous suspension; a reference to their perceived reason for an increase in joint pain. Rather, stanozolol as a DHT derivative can selectively compete with progesterone and other natural and synthetic progestins (nandrolone) for progestin receptors; yielding a reduction in progesterone mediated anti-inflammatory processes and presenting patients with a perception of increased joint discomfort.

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

It is presented most commonly as a 50 mg/mL injection or a 5 mg tablet. However, recently 75mg/ml 100 mg/mL versions have become available

Detection of use[edit]

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[edit]

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 II.

Publicized abuse cases[edit]

Synthesis[edit]

The pyrazole ring in stanozolol can be prepared from oxymetholone by the condensation of a keto-aldehyde with hydrazine.[25]

Preparation of Stanozolol.[25]

See also[edit]

References[edit]

  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. Retrieved May 24, 2010. 
  6. ^ Ivanova Sets First Record in Helsinki The Moscow Times.com, 8-8-2005
  7. ^ Hooper, James (5 October 2006). "Webcke defends 'cover-up'". Fox Sports. Retrieved 13 August 2012. 
  8. ^ WOMEN'S SHOT-PUT CHAMPION BARRED FOR LIFE The New York Times, June 2, 2004
  9. ^ Blonska Thrown Out of Long Jump BBC Sport, August 21, 2008
  10. ^ Ukrainian Blonska Given Life Ban BBC Sport, August 29, 2008
  11. ^ Jenkins, Lee (August 3, 2005). "Popular Steroid Is at the Center of Palmeiro's Case". The New York Times. Retrieved May 24, 2010. 
  12. ^ Bonds exposed: Shadows details superstar slugger's steroid use, Sports Illustrated, March 7, 2006
  13. ^ "CAS 2006/A/1149 WADA v/ FMF & José Salvador Carmona Alvarez", May 16, 2007 Accessed May 17, 2007
  14. ^ Carson, Alan (June 30, 2009). "Ex-Celt ace Hedman faces Steroids rap". The Sun (London). Retrieved November 3, 2010. 
  15. ^ Ken Pishna (2007-07-03). "Breaking News: Phil Baroni Tests Positive". MMAWeekly.com. Retrieved 2007-07-03. 
  16. ^ "Two Positive at K-1 World GP Vegas". Nokaut. August 17, 2007. Retrieved 2007-08-17. 
  17. ^ All-Star Roster Shows Up on Mitchell Report washingtonpost.com, 12-13-2007
  18. ^ Bossert, Jerry; Red, Christian (May 16, 2008). "Big Brown's legal doping a concern". Daily News (New York). 
  19. ^ http://mma-live.com/chris-leben-fails-ufc-89-drug-test/
  20. ^ Sidelnikov Suspended for Steroid Use sherdog.com, 03-03-2009
  21. ^ Sylvia Comes Clean sherdog.com, 10-13-2003
  22. ^ http://lowkick.blitzcorner.com/Strikeforce/How-Does-Cyborgs-Failed-Drug-Test-Change-the-Landscape-of-WMMA-14823
  23. ^ Sky Sports http://www1.skysports.com/olympics/story/21822/7945311 |url= missing title (help). 
  24. ^ http://www.sport24.co.za/Rugby/VarsityCup/Tuks-star-banned-for-doping-20130306
  25. ^ a b doi:10.1021/ja01515a060
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